dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-61f0ee9e53284e909a4f42fef272fe81 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O[C@H](C(=O)O)C(C)C.ClCCl>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O[C@H](C(=O)OCCl)C(C)C | C(C)O.ClCCl.C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)O[C@H](C(=O)O)C(C)C>>C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)O[C@H](C(=O)OCCl)C(C)C | [CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O:18][C@H:19]([C:20](=[O:21])[OH:22])[CH:25]([CH3:26])[CH3:27].Cl[CH2:23][Cl:24]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:1... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O[C@H](C(=O)O)C(C)C.ClCCl | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O[C@H](C(=O)OCCl)C(C)C | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2f16a3cac6d3c4085515a42267501b7a0eef68b042dbe72a334a9b3dd1458b44 | 20b23d23df2ca888376bbfdf646588e67491b315935b071cb9ba310488e4ee8f | c1ccccc1 | Cl-[CH2;D2;+0:1]-[Cl;D1;H0:2].[C:3]-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6]>>[C:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[Cl;D1;H0:2] | null | [] | null | null | null | null | 2-(N-benzyloxycarbonyl-L-valyloxy)-3-methyl-(S)-(+)-butyric acid was esterified by the method described in Example A-I-1, step d. The title compound (2.96 g) was obtained after silica gel column chromatography (0, 1, 2% ethanol in dichloromethane). Rf (2% MeOH/CHCl3) 0.85.
Conditions: See reaction.notes.procedure_detai... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carboxylic acid | Primary halide.Ester | null | null | c1ccccc1 | HCl | null | null | null | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O[C@H](C(=O)O)C(C)C.ClCCl>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O[C@H](C(=O)OCCl)C(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-370d9a4b19734d8fb3aef00c27116c59 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O[C@H](C(=O)OCCl)C(C)C.[I-]>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O[C@H](C(=O)OCI)C(C)C | C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)O[C@H](C(=O)OCCl)C(C)C.[I-]>>C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)O[C@H](C(=O)OCI)C(C)C | Cl[CH2:23][O:22][C:20]([C@@H:19]([O:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)=[O:17])[CH:25]([CH3:26])[CH3:27])=[O:21].[I-:24]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:1... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O[C@H](C(=O)OCCl)C(C)C.[I-] | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O[C@H](C(=O)OCI)C(C)C | null | null | null | Functional Group Interconversion | OtherReaction | 10bee13c50a4ba107934328c21250869f883899fc8944cf8a0ebee609aa1691d | fe69d77c5ffecf9aa0236c58528d10fdb0294a434868899e60e585d0629b72f9 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5].[I-;H0;D0:6]>>[C:4]-[C:3](=[O;D1;H0:5])-[#8:2]-[CH2;D2;+0:1]-[I;H0;D1;+0:6] | null | [] | null | null | null | null | Chloromethyl 2-(N-benzyloxycarbonyl-L-valyloxy)-3-methyl-(S)-(+)-butyrate was converted to iodide by the method described in Example A-I-1, step e to give the title compound (3.64 g) practically pure. Rf (2% MeOH/CHCl3) 0.85.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Primary halide | null | null | c1ccccc1 | Other | null | null | null | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O[C@H](C(=O)OCCl)C(C)C.[I-]>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O[C@H](C(=O)OCI)C(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-91dabd86c5564e138cd707cba42a46db | COc1ccc(CCl)cc1.O=C(O)c1ccc(O)cc1>>COc1ccc(COC(=O)c2ccc(O)cc2)cc1 | C(C)O.OC1=CC=C(C(=O)O)C=C1.COC1=CC=C(CCl)C=C1>>OC1=CC=C(C(=O)OCC2=CC=C(C=C2)OC)C=C1 | Cl[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:19][cH:18]1.[OH:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([OH:15])[cH:16][cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([OH:15])[cH:16][cH:17]2)[cH:18][cH:19]1 | COc1ccc(CCl)cc1.O=C(O)c1ccc(O)cc1 | COc1ccc(COC(=O)c2ccc(O)cc2)cc1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | O=C(OCc1ccccc1)c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6](-[OH;D1;+0:7])-[c:8]>>[O;D1;H0:5]=[C:6](-[c:8])-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 4-Hydroxybenzoic acid (1.38 g) was esterified by alkylation with 4-methoxybenzyl chloride by the method described in Example A-I-1, step a. The title compound (2.06 g) was obtained after silica gel column chromatography (0, 1, 2, 3% ethanol in dichloromethane). Rf (2% MeOH/CHCl3) 0.40.
Conditions: See reaction.notes.pr... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | c1ccccc1.c1ccccc1 | HCl | ClCCl | null | null | COc1ccc(CCl)cc1.O=C(O)c1ccc(O)cc1>ClCCl>COc1ccc(COC(=O)c2ccc(O)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6ae3b203561f432597488aa5bc496f60 | C=CCC(C)(C)C(=O)O.COc1ccc(CCl)cc1>>C=CCC(C)(C)C(=O)OCc1ccc(OC)cc1 | COC1=CC=C(CCl)C=C1.CC(C(=O)O)(CC=C)C.CC(C)([O-])C.[K+]>>CC(C(=O)OCC1=CC=C(C=C1)OC)(CC=C)C | [CH2:1]=[CH:2][CH2:3][C:4]([CH3:5])([CH3:6])[C:7](=[O:8])[OH:9].Cl[CH2:10][c:11]1[cH:12][cH:13][c:14]([O:15][CH3:16])[cH:17][cH:18]1>>[CH2:1]=[CH:2][CH2:3][C:4]([CH3:5])([CH3:6])[C:7](=[O:8])[O:9][CH2:10][c:11]1[cH:12][cH:13][c:14]([O:15][CH3:16])[cH:17][cH:18]1 | C=CCC(C)(C)C(=O)O.COc1ccc(CCl)cc1 | C=CCC(C)(C)C(=O)OCc1ccc(OC)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]>>[C:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 95.8 | [{"value": 95.8, "product": "CC(C(=O)OCC1=CC=C(C=C1)OC)(CC=C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 1 | HOUR | To a solution of 2,2-dimethyl-4-pentenoic acid (11.5 g, 90 mmol) in DMF (250 mL) at room temperature, was added potassium tert-butoxide (11.1 g, 99 mmol). The reaction mixture was stirred at 60° C. for 1 h. 4-Methoxybenzyl chloride (16.9 g, 108 mmol) was added and the reaction mixture was stirred at 60° C. for 4 h. The... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | c1ccccc1 | HCl | CN(C)C=O | 60 | 1 | C=CCC(C)(C)C(=O)O.COc1ccc(CCl)cc1>CN(C)C=O>C=CCC(C)(C)C(=O)OCc1ccc(OC)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-34c43178559645b88dc193ff2dd7b3a1 | C=CCC(C)(C)C(=O)OCc1ccc(OC)cc1.OO>>COc1ccc(COC(=O)C(C)(C)CCCO)cc1 | OO.CC(C(=O)OCC1=CC=C(C=C1)OC)(CC=C)C.B1C2CCCC1CCC2.[OH-].[Na+]>>OCCCC(C(=O)OCC1=CC=C(C=C1)OC)(C)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][C:9](=[O:10])[C:11]([CH3:12])([CH3:13])[CH2:14][CH:15]=[CH2:16])[cH:18][cH:19]1.O[OH:17]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][C:9](=[O:10])[C:11]([CH3:12])([CH3:13])[CH2:14][CH2:15][CH2:16][OH:17])[cH:18][cH:19]1 | C=CCC(C)(C)C(=O)OCc1ccc(OC)cc1.OO | COc1ccc(COC(=O)C(C)(C)CCCO)cc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | a60d6b71e8ccffcb99d0520269e8a26dfb6e6127271b139d41fb1b3b13102989 | 1ce8c00754fe0f5a8ed975b07fdc26de74ee4b991b12a7a47b4cd82546d5f701 | c1ccccc1 | O-[OH;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]-[C:6]-[CH;D2;+0:7]=[CH2;D1;+0:8]>>[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]-[C:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[OH;D1;+0:1] | null | [] | 60 | CELSIUS | 60 | MINUTE | A mixture of 4-methoxybenzyl 2,2-dimethyl-4-pentenoate (9.50 g, 38 mmol) and 9-BBN (115 mL, 57 mmol, 0.5 M in THF) was stirred at 60° C. for 60 min, whereupon the reaction mixture was cooled to −5° C. H2O (35 mL) was added, the reaction mixture was stirred for 5 min at −5° C., an aqueous solution of NaOH (35 mL, 3M) wa... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide.Allyl | Primary alcohol | null | null | c1ccccc1 | Other | O | 60 | 1 | C=CCC(C)(C)C(=O)OCc1ccc(OC)cc1.OO>O>COc1ccc(COC(=O)C(C)(C)CCCO)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5da5a07db2244bf5b88d8e9cacaf53d1 | COc1ccc(COC(=O)C(C)(C)CCCOC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)cc1>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCCC(C)(C)C(=O)O | C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCCCC(C(=O)OCC1=CC=C(C=C1)OC)(C)C.FC(C(=O)O)(F)F>>C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCCCC(C(=O)O)(C)C | COc1ccc(C[O:27][C:25]([C:22]([CH2:21][CH2:20][CH2:19][O:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)=[O:17])([CH3:23])[CH3:24])=[O:26])cc1>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:... | COc1ccc(COC(=O)C(C)(C)CCCOC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)cc1 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCCC(C)(C)C(=O)O | null | null | C(Cl)Cl | Reduction | Ester saponification (alkyl deprotection) | af4a00273af84ecb3074b1842201a78a3aac9a41d2050132ad8c8c1c9d796dee | 8d997f8b7994d8c9cf23425771b3f80d4d4830ac4e3d6552f381db244a5a65c5 | c1ccccc1 | C-O-c1:c:c:c(-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]):c:c:1>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 95.8 | [{"value": 95.8, "product": "C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCCCC(C(=O)O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 4-methoxybenzyl 5-(N-CBz-L-valyloxy)-2,2-dimethylvalerate (8.24 g, 16.5 mmol) in CH2Cl2 (100 mL) at room temperature, was added trifluoroacetic acid (5 mL). After 1 h at room temperature, the reaction mixture was concentrated under reduced pressure. The crude product was column chromatographed (silica ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Carboxylic acid | c1ccccc1 | null | c1ccccc1 | HO- | C(Cl)Cl | null | 1 | COc1ccc(COC(=O)C(C)(C)CCCOC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)cc1>C(Cl)Cl>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCCC(C)(C)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dbfa9f674327486c8236e3ab08a0e7c1 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCCC(C)(C)C(=O)O.ClCI>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCCC(C)(C)C(=O)OCCl | ClCI.C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCCCC(C(=O)O)(C)C.[OH-].C(CCC)[N+](CCCC)(CCCC)CCCC>>C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCCCC(C(=O)OCCl)(C)C | [CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O:18][CH2:19][CH2:20][CH2:21][C:22]([CH3:23])([CH3:24])[C:25](=[O:26])[OH:27].I[CH2:28][Cl:29]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCCC(C)(C)C(=O)O.ClCI | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCCC(C)(C)C(=O)OCCl | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2f16a3cac6d3c4085515a42267501b7a0eef68b042dbe72a334a9b3dd1458b44 | 20b23d23df2ca888376bbfdf646588e67491b315935b071cb9ba310488e4ee8f | c1ccccc1 | I-[CH2;D2;+0:1]-[Cl;D1;H0:2].[C:3]-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6]>>[C:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[Cl;D1;H0:2] | 59.6 | [{"value": 59.6, "product": "C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCCCC(C(=O)OCCl)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a solution of 5-(N-CBz-L-valyloxy)-2,2-dimethylvaleric acid (5.88 g, 15.5 mmol) in dioxane (100 mL), was added dropwise a 40% aqueous solution of tetrabutylammonium hydroxide (10.1 g). After stirring for 5 min, the solution was evaporated to dryness through co-evaporation with dioxane and toluene. The residue was di... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carboxylic acid | Primary halide.Ester | null | null | c1ccccc1 | HI | O1CCOCC1 | null | 0.083333 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCCC(C)(C)C(=O)O.ClCI>O1CCOCC1>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCCC(C)(C)C(=O)OCCl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f7023d254b9f4b65a57c2830ce8ec08f | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCCC(C)(C)C(=O)OCCl.[I-]>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCCC(C)(C)C(=O)OCI | C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCCCC(C(=O)OCCl)(C)C.[I-].[Na+]>>C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCCCC(C(=O)OCI)(C)C | Cl[CH2:28][O:27][C:25]([C:22]([CH2:21][CH2:20][CH2:19][O:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)=[O:17])([CH3:23])[CH3:24])=[O:26].[I-:29]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCCC(C)(C)C(=O)OCCl.[I-] | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCCC(C)(C)C(=O)OCI | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | 10bee13c50a4ba107934328c21250869f883899fc8944cf8a0ebee609aa1691d | fe69d77c5ffecf9aa0236c58528d10fdb0294a434868899e60e585d0629b72f9 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5].[I-;H0;D0:6]>>[C:4]-[C:3](=[O;D1;H0:5])-[#8:2]-[CH2;D2;+0:1]-[I;H0;D1;+0:6] | 91.1 | [{"value": 91.1, "product": "C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCCCC(C(=O)OCI)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 4 | HOUR | To a solution of chloromethyl 5-(N-CBz-L-valyloxy)-2,2-dimethylvalerate (3.85 g, 9 mmol) in acetonitrile (50 mL), was added sodium iodide (5.40 g, 36 mmol). The solution was stirred for 4 h at 60° C. The resulting suspension was filtered and the filtrate was evaporated. The residue was dissolved in CH2Cl2 and washed wi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Primary halide | null | null | c1ccccc1 | Other | C(C)#N | 60 | 4 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCCC(C)(C)C(=O)OCCl.[I-]>C(C)#N>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCCC(C)(C)C(=O)OCI |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6f293788d4df43258d54eb833145349c | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.OCCO>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCO | C1CCC(CC1)N=C=NC2CCCCC2.C(CO)O.C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)O>>C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCCO | [CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[OH:18].O[CH2:19][CH2:20][OH:21]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O:18][CH2:19][CH2:20][OH:21] | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.OCCO | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCO | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Heteroatom Alkylation and Arylation | Esterification of Carboxylic Acids | 3f9a9ace480b666da05fcfe5450d12b5c1ea5b0d435c195e1dd4bd20281604bb | dcbf04ec563ed0e9dfc79070490a028958024079a671c385858bb18cc8ec995a | c1ccccc1 | O-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3].[C:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7]>>[C:4]-[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3] | 81.3 | [{"value": 81.3, "product": "C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a mixture of DCC (11.4 g, 55 mmol), DMAP (0.611 g, 5 mmol) and ethyleneglycol (55.8 mL, 1 mol) in CH2Cl2 (300 mL) at 0° C., was added dropwise a solution of N-CBz-L-valine (12.6 g, 50 mmol) in CH2Cl2 (100 mL). After 1 h at 0° C., the temperature of the reaction mixture was allowed to assume room temperature and then... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | CN(C)C=1C=CN=CC1.C(Cl)Cl | null | 1 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.OCCO>CN(C)C=1C=CN=CC1.C(Cl)Cl>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCO |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d377cf83feed416fbef1bc8dd32fb1ec | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCO.O=C(Cl)OCCl>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCOC(=O)OCCl | C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCCO.ClC(=O)OCCl>>C(OCCOC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)(OCCl)=O | [CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O:18][CH2:19][CH2:20][OH:21].Cl[C:22](=[O:23])[O:24][CH2:25][Cl:26]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O:18][CH2... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCO.O=C(Cl)OCCl | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCOC(=O)OCCl | null | N1=CC=CC=C1 | C(Cl)Cl | Acylation | Schotten-Baumann to ester | ab2604cac7a0887c37303ad0fec59fb6a84cf40820c840730a9f7f5636dcc83e | 7ed0ec8c4c25c8af523f531911c9dd0a60119de4cab841f882ce9a65c39be54c | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4] | 52.5 | [{"value": 52.5, "product": "C(OCCOC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)(OCCl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a mixture of 2-(N-CBz-L-valyloxy)-ethanol (12.0 g, 40.6 mmol) and pyridine (19.7 mL, 0.24 mmol) in CH2Cl2 (300 mL) at 0° C., was added dropwise chloromethyl chloroformate (10.5 g, 81.2 mmol). After 30 min at 0° C., the reaction mixture was washed with H2O (200 mL). The H2O phase was washed with CH2Cl2 (100 mL) and t... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary alcohol | Carbonic Ester | null | null | c1ccccc1 | HCl | N1=CC=CC=C1.C(Cl)Cl | null | 0.5 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCO.O=C(Cl)OCCl>N1=CC=CC=C1.C(Cl)Cl>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCOC(=O)OCCl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-efe6847848e54281b6087f19f3eb7e69 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCOC(=O)OCCl.[I-]>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCOC(=O)OCI | C(OCCOC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)(OCCl)=O.[I-].[Na+]>>C(OCCOC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)(OCI)=O | Cl[CH2:25][O:24][C:22]([O:21][CH2:20][CH2:19][O:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)=[O:17])=[O:23].[I-:26]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O:18][CH2:... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCOC(=O)OCCl.[I-] | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCOC(=O)OCI | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | 22e4ae0c85daffd0078fd40b928ca1a4ed497239b66c1b767f5c2602965f1e0a | e5953f4c2f3e929ebd5c80667db5cd8a1df5fb6bd8f8f4de947f99af74ff7227 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3](-[#8:4])=[O;D1;H0:5].[I-;H0;D0:6]>>[#8:4]-[C:3](=[O;D1;H0:5])-[#8:2]-[CH2;D2;+0:1]-[I;H0;D1;+0:6] | 94.1 | [{"value": 94.1, "product": "C(OCCOC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)(OCI)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 4 | HOUR | To a solution of 2-(N-CBz-L-valyloxy)-ethyl chloromethyl carbonate (3.88 g, 10 mmol) in acetonitrile (50 mL), was added sodium iodide (7.50 g, 50 mmol). The solution was stirred for 4 h at 60° C. The resulting suspension was filtered and the filtrate was evaporated. The residue was dissolved in CH2Cl2 and washed with a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbonic Ester | Primary halide | null | null | c1ccccc1 | Other | C(C)#N | 60 | 4 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCOC(=O)OCCl.[I-]>C(C)#N>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCOC(=O)OCI |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ac0ad24d7bde4d719570c09c5d7bd9ae | CC(C)[C@@H](NC(=O)OCc1ccccc1)C(=O)O.COc1ccc(COC(=O)C(C)(C)C)cc1>>CC(C)[C@@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)C(=O)O | COC1=CC=C(COC(C(C)(C)C)=O)C=C1.C(=O)(OCC1=CC=CC=C1)N[C@H](C(C)C)C(=O)O.C1CCC(CC1)N=C=NC2CCCCC2>>CC(C(=O)O)(COC([C@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)C | [CH3:1][CH:2]([CH3:3])[C@@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[OH:18].COc1ccc(C[O:25][C:23]([C:20]([CH3:19])([CH3:21])[CH3:22])=[O:24])cc1>>[CH3:1][CH:2]([CH3:3])[C@@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])... | CC(C)[C@@H](NC(=O)OCc1ccccc1)C(=O)O.COc1ccc(COC(=O)C(C)(C)C)cc1 | CC(C)[C@@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)C(=O)O | null | CN(C1=CC=NC=C1)C | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | fa114fc659c6ab41d73e72319b0f3b912b30819cdb9dad87e31e219e414ae723 | 3e9ddf61382439b4601a41a3b5fba1e61f883ac205600a1e7e0bcb8a6114c6db | c1ccccc1 | C-O-c1:c:c:c(-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[CH3;D1;+0:7]):c:c:1.[C:8]-[C:9](=[O;D1;H0:10])-[OH;D1;+0:11]>>[C:8]-[C:9](=[O;D1;H0:10])-[O;H0;D2;+0:11]-[CH2;D2;+0:7]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | 18 | HOUR | To a solution of 2,2-dimethyl propionic acid 4-methoxybenzyl ester (4.7 g, 20 mmole) and N-CBz-D-valine (5.5 g, 22 mmole) in dichloromethane (100 ml) were added 4-dimethyaminopyridine (305 mg, 2.5 mmole) and DCC (5.15 g, 25 mmole). After 18 hr, the solution was washed successively with sodium bicarbonate aqueous soluti... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Ether | Carboxylic acid.Ester | c1ccccc1 | null | c1ccccc1 | HO- | CN(C1=CC=NC=C1)C.ClCCl | null | 18 | CC(C)[C@@H](NC(=O)OCc1ccccc1)C(=O)O.COc1ccc(COC(=O)C(C)(C)C)cc1>CN(C1=CC=NC=C1)C.ClCCl>CC(C)[C@@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-74c2111d57ea4efa849d158c09f1a797 | CC(C)[C@@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)C(=O)O.ClCI>>CC(C)[C@@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)C(=O)OCCl | CC(C(=O)O)(COC([C@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)C.[OH-].C(CCC)[N+](CCCC)(CCCC)CCCC.ClCI>>ClCOC(C(COC([C@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)(C)C)=O | [CH3:1][CH:2]([CH3:3])[C@@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O:18][CH2:19][C:20]([CH3:21])([CH3:22])[C:23](=[O:24])[OH:25].I[CH2:26][Cl:27]>>[CH3:1][CH:2]([CH3:3])[C@@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:1... | CC(C)[C@@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)C(=O)O.ClCI | CC(C)[C@@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)C(=O)OCCl | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2f16a3cac6d3c4085515a42267501b7a0eef68b042dbe72a334a9b3dd1458b44 | 20b23d23df2ca888376bbfdf646588e67491b315935b071cb9ba310488e4ee8f | c1ccccc1 | I-[CH2;D2;+0:1]-[Cl;D1;H0:2].[C:3]-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6]>>[C:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[Cl;D1;H0:2] | null | [] | null | null | 18 | HOUR | (2,2-dimethyl-3-(N-CBz-D-valyloxy)-propionic acid (4.5 g, 12.8 mmole) was dissolved in dioxane (20 ml). To the solution was added tetrabutylammonium hydroxide aqueous solution (40%, 8.3 ml, 12.8 mmole). The solution was dried in vacuo, and it was coevaporated with toluene several times. The residue was dissolved in met... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carboxylic acid | Primary halide.Ester | null | null | c1ccccc1 | HI | O1CCOCC1 | null | 18 | CC(C)[C@@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)C(=O)O.ClCI>O1CCOCC1>CC(C)[C@@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)C(=O)OCCl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ea743c27e60e434ba747b637b192a3f3 | CC(C)[C@@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)C(=O)OCCl.[I-]>>CC(C)[C@@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)C(=O)OCI | ClCOC(C(COC([C@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)(C)C)=O.[I-].[Na+]>>ICOC(C(COC([C@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)(C)C)=O | Cl[CH2:26][O:25][C:23]([C:20]([CH2:19][O:18][C:16]([C@@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)=[O:17])([CH3:21])[CH3:22])=[O:24].[I-:27]>>[CH3:1][CH:2]([CH3:3])[C@@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:1... | CC(C)[C@@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)C(=O)OCCl.[I-] | CC(C)[C@@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)C(=O)OCI | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | 10bee13c50a4ba107934328c21250869f883899fc8944cf8a0ebee609aa1691d | fe69d77c5ffecf9aa0236c58528d10fdb0294a434868899e60e585d0629b72f9 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5].[I-;H0;D0:6]>>[C:4]-[C:3](=[O;D1;H0:5])-[#8:2]-[CH2;D2;+0:1]-[I;H0;D1;+0:6] | null | [] | null | null | null | null | 2,2-Dimethyl-3-(N-CBz-D-valyloxy)-propionic acid chloromethyl ester (2.4 g, 6 mmole) was dissolved in acetonitrile (30 ml). Sodium iodide (1.26 g, 8.4 mmole) was added to the solution. After reaction at 70° C. for 2 hr, the reaction mixture was filtered and the residue was dissolved in methylene chloride (20 ml) and re... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Primary halide | null | null | c1ccccc1 | Other | C(C)#N | null | null | CC(C)[C@@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)C(=O)OCCl.[I-]>C(C)#N>CC(C)[C@@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)C(=O)OCI |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5add802c0df94ca59baad3fa9997c470 | CC(C)(C)OC(=O)CCCBr.CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCCC(=O)OC(C)(C)C | C([O-])(O)=O.[Na+].CC(C)([O-])C.[K+].C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)O.C(C)(C)(C)OC(CCCBr)=O>>C(C)(C)(C)OC(CCCOC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)=O | Br[CH2:19][CH2:20][CH2:21][C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28].[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[OH:18]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:1... | CC(C)(C)OC(=O)CCCBr.CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCCC(=O)OC(C)(C)C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#8:5])=[O;D1;H0:6].[C:7]-[C:8](=[O;D1;H0:9])-[OH;D1;+0:10]>>[#8:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:10]-[C:8](-[C:7])=[O;D1;H0:9] | null | [] | null | null | 10 | MINUTE | N-CBz-L-valine (16.25 g, 65 mmole) was dissolved in DMF (40 ml). To the solution was added potassium t-butoxide (7.24 g, 65 mmole). After 10 min, 4-bromobutyric acid t-butyl ester (12 g, 53 mmole) was added. The reaction mixture was kept at 65° C. for 2.5 hr and then poured into sodium bicarbonate aqueous solution and ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | c1ccccc1 | HBr | CN(C)C=O | null | 0.166667 | CC(C)(C)OC(=O)CCCBr.CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O>CN(C)C=O>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCCC(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-10ee54ec1b354fc8ba1f7e6a405322d6 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCCC(=O)OC(C)(C)C.ClCI>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCCC(=O)OCCl | [OH-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(C)(C)OC(CCCOC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)=O.FC(C(=O)O)(F)F.ClCI>>ClCOC(CCCOC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)=O | CC(C)(C)[O:24][C:22]([CH2:21][CH2:20][CH2:19][O:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)=[O:17])=[O:23].I[CH2:25][Cl:26]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCCC(=O)OC(C)(C)C.ClCI | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCCC(=O)OCCl | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 385841bdc77d5801a502c6a772ae3ab48348c27c634481f5cadd962b632f7ae9 | cbaef06e3b5b8699ab3eeed9b7ece4c48dcd2b2c60b6f8c6f857f5d60634f513 | c1ccccc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].I-[CH2;D2;+0:5]-[Cl;D1;H0:6]>>[C:3]-[C:2](=[O;D1;H0:4])-[O;H0;D2;+0:1]-[CH2;D2;+0:5]-[Cl;D1;H0:6] | null | [] | null | null | 18 | HOUR | 4-(N-CBz-L-valyloxy) butyric acid t-butyl ester (20 g, 50.8 mmole) was treated with trifluoroacetic acid (30 ml) at 0° C. for 3 h and then evaporated. The residue was coevaporated with toluene several time. The intermediate acid (2.56 g, 7.6 mmole) was dissolved in dioxane (10 ml) and to the solution was added tetrabut... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Ester.Boc | Primary halide.Ester | null | null | c1ccccc1 | HI | O1CCOCC1 | null | 18 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCCC(=O)OC(C)(C)C.ClCI>O1CCOCC1>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCCC(=O)OCCl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1833c421a063426589e0c1652741d270 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCCC(=O)OCCl.[I-]>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCCC(=O)OCI | ClCOC(CCCOC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)=O.[I-].[Na+]>>ICOC(CCCOC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)=O | Cl[CH2:25][O:24][C:22]([CH2:21][CH2:20][CH2:19][O:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)=[O:17])=[O:23].[I-:26]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O:18][CH... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCCC(=O)OCCl.[I-] | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCCC(=O)OCI | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | 10bee13c50a4ba107934328c21250869f883899fc8944cf8a0ebee609aa1691d | fe69d77c5ffecf9aa0236c58528d10fdb0294a434868899e60e585d0629b72f9 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5].[I-;H0;D0:6]>>[C:4]-[C:3](=[O;D1;H0:5])-[#8:2]-[CH2;D2;+0:1]-[I;H0;D1;+0:6] | null | [] | null | null | null | null | 4-(N-CBz-L-valyloxy) butyric acid chloromethyl ester (1.54 g, 4 mmole) was dissolved in acetonitrile (15 ml). Sodium iodide (840 mg, 5.6 mmole) was added to the solution. After reaction at 55° C. for 3 hr, the reaction mixture was filtered and the residue was dissolved in methylene chloride (20 ml) and refiltered. The ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Primary halide | null | null | c1ccccc1 | Other | C(C)#N | null | null | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCCC(=O)OCCl.[I-]>C(C)#N>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCCC(=O)OCI |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c1b5f9b9749241d99f999a1d1f16fad0 | COc1ccc(CCl)cc1.O=C(O)c1cccc(O)c1>>COc1ccc(COC(=O)c2cccc(O)c2)cc1 | COC1=CC=C(CCl)C=C1.OC=1C=C(C(=O)O)C=CC1.[K].CC(C)([O-])C>>OC=1C=C(C(=O)OCC2=CC=C(C=C2)OC)C=CC1 | Cl[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:19][cH:18]1.[OH:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][c:15]([OH:16])[cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][c:15]([OH:16])[cH:17]2)[cH:18][cH:19]1 | COc1ccc(CCl)cc1.O=C(O)c1cccc(O)c1 | COc1ccc(COC(=O)c2cccc(O)c2)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | O=C(OCc1ccccc1)c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6](-[OH;D1;+0:7])-[c:8]>>[O;D1;H0:5]=[C:6](-[c:8])-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 1 | HOUR | To a solution of 3-hydroxybenzoic acid (6.9 g, 50 mmole) in DMF (100 ml) was added potassium-tert.-butoxide (6.17 g, 55 mmole) and the mixture was stirred at room temperature for one hour. 4-Methoxybenzyl chloride (9.4 g, 60 mmole) was added and the mixture was stirred for 16 hours at 60° C. The mixture was evaporated ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | c1ccccc1.c1ccccc1 | HCl | CN(C)C=O | null | 1 | COc1ccc(CCl)cc1.O=C(O)c1cccc(O)c1>CN(C)C=O>COc1ccc(COC(=O)c2cccc(O)c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bdcc6a57c94444a9bf5ef696bb0a5468 | COc1ccc(Cc2c(OC(=O)[C@@H](NC(=O)OCc3ccccc3)C(C)C)cccc2C(=O)[O-])cc1>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1cccc(C(=O)O)c1 | COC1=CC=C(CC2=C(C(=O)[O-])C=CC=C2OC([C@@H](NC(=O)OCC2=CC=CC=C2)C(C)C)=O)C=C1.FC(C(=O)O)(F)F>>C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OC=1C=C(C(=O)O)C=CC1 | COc1ccc(C[c:27]2[c:19]([O:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)=[O:17])[cH:20][cH:21][cH:22][c:23]2[C:24](=[O:25])[O-:26])cc1>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[... | COc1ccc(Cc2c(OC(=O)[C@@H](NC(=O)OCc3ccccc3)C(C)C)cccc2C(=O)[O-])cc1 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1cccc(C(=O)O)c1 | null | null | ClCCl | Reduction | OtherReaction | 769a404e671d0d594f18f3ad3a2501c86e8dc547c4c19035456800f300835e25 | fc36b78de76f2c5141892df769222d9a793f25ecdae731308a2cae6bc6b43b17 | O=C(CNC(=O)OCc1ccccc1)Oc1ccccc1 | C-O-c1:c:c:c(-C-[c;H0;D3;+0:1](:[c:2](-[#8:3]-[C:4]=[O;D1;H0:5]):[c:6]):[c:7](-[C:8](-[O-;H0;D1:9])=[O;D1;H0:10]):[c:11]):c:c:1>>[O;D1;H0:5]=[C:4]-[#8:3]-[c:2](:[c:6]):[cH;D2;+0:1]:[c:7](-[C:8](=[O;D1;H0:10])-[OH;D1;+0:9]):[c:11] | null | [] | null | null | 2 | HOUR | To a solution of 4-methoxybenzyl-3-(N-benzyloxycarbonyl-L-valyloxy)-benzoate (13.7 g, 27.8 mmole) in dichloromethane (150 ml) was added trifluoroacetic acid (20 ml) and the mixture was stirred for 2 hours at room temperature. The solution was evaporated under reduced pressure and the product crystallized from toluene. ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Carboxylic acid | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | ClCCl | null | 2 | COc1ccc(Cc2c(OC(=O)[C@@H](NC(=O)OCc3ccccc3)C(C)C)cccc2C(=O)[O-])cc1>ClCCl>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1cccc(C(=O)O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-127fc892cc714e3a87233a5a5f30f622 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1cccc(C(=O)O)c1.ClCI>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1cccc(C(=O)OCCl)c1 | ClCI.C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OC=1C=C(C(=O)O)C=CC1.[OH-].C(CCC)[N+](CCCC)(CCCC)CCCC>>C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OC=1C=C(C(=O)OCCl)C=CC1 | [CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O:18][c:19]1[cH:20][cH:21][cH:22][c:23]([C:24](=[O:25])[OH:26])[cH:29]1.I[CH2:27][Cl:28]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:1... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1cccc(C(=O)O)c1.ClCI | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1cccc(C(=O)OCCl)c1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2f16a3cac6d3c4085515a42267501b7a0eef68b042dbe72a334a9b3dd1458b44 | 20b23d23df2ca888376bbfdf646588e67491b315935b071cb9ba310488e4ee8f | O=C(CNC(=O)OCc1ccccc1)Oc1ccccc1 | I-[CH2;D2;+0:1]-[Cl;D1;H0:2].[O;D1;H0:3]=[C:4](-[OH;D1;+0:5])-[c:6]>>[Cl;D1;H0:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[C:4](=[O;D1;H0:3])-[c:6] | null | [] | null | null | 2 | HOUR | To a solution of 3-(N-benzyloxycarbonyl-valyloxy)benzoic acid (7.42 g, 20 mmole) in 1,4-dioxane (100 ml) was added a 40% solution of tetrabutylammonium hydroxide (12.97 g, 20 mmole) and the mixture was stirred 2 hours at room temperature. The mixture was evaporated under reduced pressure and co-evaporated two times wit... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carboxylic acid | Primary halide.Ester | null | null | c1ccccc1.c1ccccc1 | HI | O1CCOCC1 | null | 2 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1cccc(C(=O)O)c1.ClCI>O1CCOCC1>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1cccc(C(=O)OCCl)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5f12592096b94cda8e243ca27d971988 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1cccc(C(=O)OCCl)c1.[I-]>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1cccc(C(=O)OCI)c1 | C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OC=1C=C(C(=O)OCCl)C=CC1.[I-].[Na+]>>C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OC=1C=C(C(=O)OCI)C=CC1 | Cl[CH2:27][O:26][C:24]([c:23]1[cH:22][cH:21][cH:20][c:19]([O:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)=[O:17])[cH:29]1)=[O:25].[I-:28]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:1... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1cccc(C(=O)OCCl)c1.[I-] | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1cccc(C(=O)OCI)c1 | null | null | CC(=O)C | Functional Group Interconversion | OtherReaction | 10bee13c50a4ba107934328c21250869f883899fc8944cf8a0ebee609aa1691d | fe69d77c5ffecf9aa0236c58528d10fdb0294a434868899e60e585d0629b72f9 | O=C(CNC(=O)OCc1ccccc1)Oc1ccccc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c:5].[I-;H0;D0:6]>>[I;H0;D1;+0:6]-[CH2;D2;+0:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c:5] | null | [] | null | null | 8 | HOUR | To a solution of chloromethyl 3-(N-benzyloxycarbonyl-L-valyloxy)-benzoate (2.0 g, 4.76 mmole) in dry acetone (30 ml) was added sodium iodide (3.15 g, 21 mmole) and the mixture was stirred overnight at room temperature. The mixture was evaporated under reduced pressure and extracted with ethyl actate/water. The organic ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Primary halide | null | null | c1ccccc1.c1ccccc1 | Other | CC(=O)C | null | 8 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1cccc(C(=O)OCCl)c1.[I-]>CC(=O)C>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1cccc(C(=O)OCI)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bcc8e27aeab242b28597087af1c81f63 | CCC=CC(CC(=O)[O-])OC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCC(=O)O | Cl.S([O-])(O)=O.[Na+].[Mn](=O)(=O)(=O)[O-].[K+].C(=CCC)C(CC(=O)[O-])OC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O>>C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OCCC(=O)O | CCC=C[CH:19]([O:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)=[O:17])[CH2:20][C:21](=[O:22])[O-:23]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O:18][CH2:19][CH2:20][C:21]... | CCC=CC(CC(=O)[O-])OC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCC(=O)O | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | C1=CC=CC=C1.O | Miscellaneous | OtherReaction | 6964d317f96e5ec443b628aa20adcf9ce59df51c6e752f0ba688d0106c9a8846 | 25b53624051778d7b93b11291d8ead79ccbffb1e81819be753f1ab1ae25d1334 | c1ccccc1 | C-C-C=C-[CH;D3;+0:1](-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5])-[C:6]-[C:7](-[O-;H0;D1:8])=[O;D1;H0:9]>>[C:4]-[C:3](=[O;D1;H0:5])-[#8:2]-[CH2;D2;+0:1]-[C:6]-[C:7](=[O;D1;H0:9])-[OH;D1;+0:8] | null | [] | 5 | CELSIUS | 2 | HOUR | To a solution of 3-buten-1-yl-3-(N-benzyloxycarbonyl-L-valyloxy)-propionate (9.2 g, 30 mmole) in 150 ml benzene was added tetrabutylammonium bromide (1.62 g, 5 mmole) and 100 ml water. The mixture was cooled to about 5° C. and potassium permanganate (14.82 g, 90 mmole) was added in portions. The mixture was stirred 2 h... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid.Ester | null | null | c1ccccc1 | Other | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C1=CC=CC=C1.O | 5 | 2 | CCC=CC(CC(=O)[O-])OC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C1=CC=CC=C1.O>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCC(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-60abc4731e7a4155b94e64e9ccfee06b | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCC(=O)O.ClCI>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCC(=O)OCCl | ClCI.C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OCCC(=O)O.[OH-].C(CCC)[N+](CCCC)(CCCC)CCCC>>C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OCCC(=O)OCCl | [CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O:18][CH2:19][CH2:20][C:21](=[O:22])[OH:23].I[CH2:24][Cl:25]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O:18][CH2:19][CH... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCC(=O)O.ClCI | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCC(=O)OCCl | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2f16a3cac6d3c4085515a42267501b7a0eef68b042dbe72a334a9b3dd1458b44 | 20b23d23df2ca888376bbfdf646588e67491b315935b071cb9ba310488e4ee8f | c1ccccc1 | I-[CH2;D2;+0:1]-[Cl;D1;H0:2].[C:3]-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6]>>[C:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[Cl;D1;H0:2] | null | [] | null | null | 2 | HOUR | To a solution of 3-(N-benzyloxycarbonyl-L-valyloxy)propanoic acid (5.2 g, 16.08 mmole) in 1,4-dioxane (50 ml) was added a 40% solution of tetrabutylammonium hydroxide (10.43 g, 16.08 mmole) and the mixture was stirred 2 hours at room temperature. The mixture was evaporated under reduced pressure and co-evaporated two t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carboxylic acid | Primary halide.Ester | null | null | c1ccccc1 | HI | O1CCOCC1 | null | 2 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCC(=O)O.ClCI>O1CCOCC1>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCC(=O)OCCl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d34fd30451ab471999f96eb0b4131d24 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCC(=O)OCCl.[I-]>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCC(=O)OCI | C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OCCC(=O)OCCl.[I-].[Na+]>>ICOC(CCOC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)=O | Cl[CH2:24][O:23][C:21]([CH2:20][CH2:19][O:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)=[O:17])=[O:22].[I-:25]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O:18][CH2:19][CH... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCC(=O)OCCl.[I-] | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCC(=O)OCI | null | null | CC(=O)C | Functional Group Interconversion | OtherReaction | 10bee13c50a4ba107934328c21250869f883899fc8944cf8a0ebee609aa1691d | fe69d77c5ffecf9aa0236c58528d10fdb0294a434868899e60e585d0629b72f9 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5].[I-;H0;D0:6]>>[C:4]-[C:3](=[O;D1;H0:5])-[#8:2]-[CH2;D2;+0:1]-[I;H0;D1;+0:6] | null | [] | null | null | 8 | HOUR | To a solution of chloromethyl 3-(N-benzyloxycarbonyl-L-valyloxy)-propionate (2.05 g, 5.51 mmole) in dry acetone (50 ml) was added sodium iodide (4.12 g, 27.5 mmole) and the mixture was stirred overnight at room temperature. The mixture was evaporated under reduced pressure and extracted with ethyl acetate water. The or... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Primary halide | null | null | c1ccccc1 | Other | CC(=O)C | null | 8 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCC(=O)OCCl.[I-]>CC(=O)C>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCC(=O)OCI |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9c84975618664030a01291419378dd4f | CC(C)(CO)CO.CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)CO | C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)O.CC(CO)(CO)C.C1(CCCCC1)N=C=NC1CCCCC1>>C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OCC(CO)(C)C | O[CH2:19][C:20]([CH3:21])([CH3:22])[CH2:23][OH:24].[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[OH:18]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O:18][CH2:19][C:20]... | CC(C)(CO)CO.CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)CO | null | CN(C1=CC=NC=C1)C | C(Cl)Cl | Heteroatom Alkylation and Arylation | Esterification of Carboxylic Acids | 3f9a9ace480b666da05fcfe5450d12b5c1ea5b0d435c195e1dd4bd20281604bb | dcbf04ec563ed0e9dfc79070490a028958024079a671c385858bb18cc8ec995a | c1ccccc1 | O-[CH2;D2;+0:1]-[C:2](-[C:3])(-[C;D1;H3:4])-[C;D1;H3:5].[C:6]-[C:7](=[O;D1;H0:8])-[OH;D1;+0:9]>>[C:3]-[C:2](-[C;D1;H3:4])(-[C;D1;H3:5])-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-[C:7](-[C:6])=[O;D1;H0:8] | 88.6 | [{"value": 87.0, "product": "C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OCC(CO)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.6, "product": "C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OCC(CO)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 23 | HOUR | A mixture of N-benzyloxycarbonyl-L-valine (2.50 g, 10.0 mmol), 2,2-dimethyl-1,3-propanediol (5.30 g, 50.9 mmol), dicyclohexylcarbodiimide (2.60 g, 12.6 mmol), and 4-dimethylaminopyridine (125 mg, 1.0 mmol) in 100 mL dry CH2Cl2 was stirred for 23 h. The reaction mixture was filtered and washed successively with 50 mL ea... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | CN(C1=CC=NC=C1)C.C(Cl)Cl | null | 23 | CC(C)(CO)CO.CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O>CN(C1=CC=NC=C1)C.C(Cl)Cl>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)CO |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1222edc98359491496ffe3b491ce50a1 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)CO.O=C(Cl)OCCl>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)COC(=O)OCCl | ClC(=O)OCCl.C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OCC(CO)(C)C.N1=CC=CC=C1>>C(OCC(COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)(C)C)(OCCl)=O | [CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O:18][CH2:19][C:20]([CH3:21])([CH3:22])[CH2:23][OH:24].Cl[C:25](=[O:26])[O:27][CH2:28][Cl:29]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)CO.O=C(Cl)OCCl | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)COC(=O)OCCl | null | null | C(Cl)Cl | Acylation | Schotten-Baumann to ester | ab2604cac7a0887c37303ad0fec59fb6a84cf40820c840730a9f7f5636dcc83e | 7ed0ec8c4c25c8af523f531911c9dd0a60119de4cab841f882ce9a65c39be54c | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4] | 95 | [{"value": 95.0, "product": "C(OCC(COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)(C)C)(OCCl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.8, "product": "C(OCC(COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)(C)C)(OCCl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Chloromethyl chloroformate (1.50 mL, 16.6 mmol) was added to a solution of the alcohol (2.74 g, 8.12 mmol) from step (a) and pyridine (4.9 mL, 61 mmol) in 40 mL dry CH2Cl2, in an ice bath. After stirring for 1 h, the mixture was diluted with CH2Cl2 and washed successively with water, saturated NaHCO3, and brine. The or... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary alcohol | Carbonic Ester | null | null | c1ccccc1 | HCl | C(Cl)Cl | null | 1 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)CO.O=C(Cl)OCCl>C(Cl)Cl>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)COC(=O)OCCl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-71d178c0e41e47e897e88702e8948b62 | CC(C)(O)CO.CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)O | C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)O.C1(CCCCC1)N=C=NC1CCCCC1.CC(CO)(C)O.CN(C)C=O>>C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OCC(C)(O)C | [OH:18][CH2:19][C:20]([CH3:21])([CH3:22])[OH:23].O[C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)=[O:17]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O:18][CH2:19][C:20]([CH3:21... | CC(C)(O)CO.CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)O | null | CN(C1=CC=NC=C1)C | C(Cl)Cl | Acylation | Esterification of Carboxylic Acids | d9bd78214ee7dbc907e499722ae01849a72d188753963443e5df9fe42c31c43b | 3652e761944e8ef7ee40675a156c8ae39909c72166786934d88652debf2ec1ac | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[C:9]-[OH;D1;+0:10]>>[C:8]-[C:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7] | 88.9 | [{"value": 88.9, "product": "C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OCC(C)(O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 10 | CELSIUS | 5 | HOUR | N-Benzyloxycarbonyl-L-valine (2.02 g, 8.0 mmol), 4-dimethylaminopyridine (100 mg, 0.8 mmol), and), and dicyclohexylcarbodiimide (2.04 g, 9.9 mmol, in 20 mL CH2Cl2) were added to 2-methyl-1,2-propanediol (12.2 mmol) in 30 mL dry CH2Cl2, with cooling in an ice bath. DMF (5 mL) was added. After stirring for 5 h at 10° C.,... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | CN(C1=CC=NC=C1)C.C(Cl)Cl | 10 | 5 | CC(C)(O)CO.CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O>CN(C1=CC=NC=C1)C.C(Cl)Cl>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7816bbdb33bd49adbb5d35fffe45bea2 | COc1ccc(CC(Cc2ccc(OC(=O)[C@@H](NC(=O)OCc3ccccc3)C(C)C)c(OC(=O)[C@@H](NC(=O)OCc3ccccc3)C(C)C)c2)C(=O)[O-])cc1>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1ccc(CCC(=O)O)cc1OC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C | COC1=CC=C(CC(C(=O)[O-])CC2=CC(=C(C=C2)OC([C@@H](NC(=O)OCC2=CC=CC=C2)C(C)C)=O)OC([C@@H](NC(=O)OCC2=CC=CC=C2)C(C)C)=O)C=C1.C(=O)(C(F)(F)F)O>>C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OC=1C=C(CCC(=O)O)C=CC1OC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O | COc1ccc(C[CH:24]([CH2:23][c:22]2[cH:21][cH:20][c:19]([O:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)=[O:17])[c:29]([O:30][C:31](=[O:32])[C@@H:33]([NH:34][C:35](=[O:36])[O:37][CH2:38][c:39]3[cH:40][cH:41][cH:42][cH:43][cH:44]3)[CH:45]([CH3:46])[CH3:... | COc1ccc(CC(Cc2ccc(OC(=O)[C@@H](NC(=O)OCc3ccccc3)C(C)C)c(OC(=O)[C@@H](NC(=O)OCc3ccccc3)C(C)C)c2)C(=O)[O-])cc1 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1ccc(CCC(=O)O)cc1OC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C | null | null | ClCCl | Reduction | OtherReaction | 63b60d5a898a00ae9b34da7ba2b91d97ecc242a88bc6ab4376369c26968079ae | fc36b78de76f2c5141892df769222d9a793f25ecdae731308a2cae6bc6b43b17 | O=C(CNC(=O)OCc1ccccc1)Oc1ccccc1OC(=O)CNC(=O)OCc1ccccc1 | C-O-c1:c:c:c(-C-[CH;D3;+0:1](-[C:2]-[c:3])-[C:4](-[O-;H0;D1:5])=[O;D1;H0:6]):c:c:1>>[O;D1;H0:6]=[C:4](-[OH;D1;+0:5])-[CH2;D2;+0:1]-[C:2]-[c:3] | 80 | [{"value": 80.0, "product": "C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OC=1C=C(CCC(=O)O)C=CC1OC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.4, "product": "C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OC=1C=C(CCC(=O)O)C=CC1OC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O", "details":... | null | null | null | null | 4-Methoxybenzyl-3,4-di-(N-CBZ-L-valyloxy)hydrocinnamate (10 g, 13 mmol) was dissolved in dichloromethane and 1,1,1 trifluoroacetic acid (30 ml) and left at ambient temperature for 3.5 h. Evaporation under reduced pressure and purification by chromatography (chloroform-methanol, 10:1) yielded 6.7 g (80%) pure title prod... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Carboxylic acid | c1ccccc1 | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | ClCCl | null | null | COc1ccc(CC(Cc2ccc(OC(=O)[C@@H](NC(=O)OCc3ccccc3)C(C)C)c(OC(=O)[C@@H](NC(=O)OCc3ccccc3)C(C)C)c2)C(=O)[O-])cc1>ClCCl>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1ccc(CCC(=O)O)cc1OC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bbb1328e493c4550b5d471a3230a4e66 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1ccc(CCC(=O)OCCl)cc1OC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C.[I-]>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1ccc(CCC(=O)OCI)cc1OC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C | C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OC=1C=C(CCC(=O)OCCl)C=CC1OC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O.[I-].[Na+]>>C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OC=1C=C(CCC(=O)OCI)C=CC1OC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O | Cl[CH2:28][O:27][C:25]([CH2:24][CH2:23][c:22]1[cH:21][cH:20][c:19]([O:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)=[O:17])[c:31]([O:32][C:33](=[O:34])[C@@H:35]([NH:36][C:37](=[O:38])[O:39][CH2:40][c:41]2[cH:42][cH:43][cH:44][cH:45][cH:46]2)[CH:47](... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1ccc(CCC(=O)OCCl)cc1OC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C.[I-] | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1ccc(CCC(=O)OCI)cc1OC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | 10bee13c50a4ba107934328c21250869f883899fc8944cf8a0ebee609aa1691d | fe69d77c5ffecf9aa0236c58528d10fdb0294a434868899e60e585d0629b72f9 | O=C(CNC(=O)OCc1ccccc1)Oc1ccccc1OC(=O)CNC(=O)OCc1ccccc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5].[I-;H0;D0:6]>>[C:4]-[C:3](=[O;D1;H0:5])-[#8:2]-[CH2;D2;+0:1]-[I;H0;D1;+0:6] | 90 | [{"value": 90.0, "product": "C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OC=1C=C(CCC(=O)OCI)C=CC1OC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.2, "product": "C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OC=1C=C(CCC(=O)OCI)C=CC1OC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O", "detai... | 65 | CELSIUS | null | null | Chloromethyl 3,4-di-(N-CBZ-L-valyloxy)hydrocinnamate (1.9 g, 2.7 mmol) and sodium iodide (2 g, 13.3 mmol) were dissolved in acetonitrile (50 ml) and heated to 65° C. for 60 min. The solvent was removed under reduced pressure and the residue was taken up in dichloromethane and filtrated. Removal of the solvent and purif... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Primary halide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | Other | C(C)#N | 65 | null | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1ccc(CCC(=O)OCCl)cc1OC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C.[I-]>C(C)#N>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1ccc(CCC(=O)OCI)cc1OC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d207e27a45db4852acedf58671452cf2 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.Oc1cccc(O)c1>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1cccc(O)c1 | C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)O.OC1=CC(=CC=C1)O>>C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OC=1C=C(C=CC1)O | O[C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)=[O:17].[OH:18][c:19]1[cH:20][cH:21][cH:22][c:23]([OH:24])[cH:25]1>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O:18][c:19]1[cH:2... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.Oc1cccc(O)c1 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1cccc(O)c1 | null | CN(C1=CC=NC=C1)C | CN(C)C=O | Protection | Mitsunobu esterification | 1cb1611b2951091632a151ab5081ff56216b7f18870755e817fb3880bd0f0e0f | 9e53e3e7cecdca657d645cff0c754541858d0ddbb0fd44141675c3a705d7f934 | O=C(CNC(=O)OCc1ccccc1)Oc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11] | 79.4 | [{"value": 79.0, "product": "C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OC=1C=C(C=CC1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.4, "product": "C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OC=1C=C(C=CC1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | CBz-L-valine (10 g, 40 mmol), 1,3-dihydroxybenzene (8.7 g, 79 mmol) N,N′dicychlohexylcarbodiimide (10.2 g, 44 mmol) and 4-dimethylaminopyridine (2.4 g, 20 mmol) were dissolved in DMF (50 ml) and left at ambient temperature overnight. The reaction mixture was filtered, the solvent removed under reduced pressure and the ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol | Ester | null | null | c1ccccc1.c1ccccc1 | HO- | CN(C1=CC=NC=C1)C.CN(C)C=O | null | 8 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.Oc1cccc(O)c1>CN(C1=CC=NC=C1)C.CN(C)C=O>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1cccc(O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7b3a7ee360b1461e8cd3f42ab200f8fa | COc1ccc(CCl)cc1.O=C(O)Cc1ccccc1O>>COc1ccc(COC(=O)Cc2ccccc2O)cc1 | COC1=CC=C(CCl)C=C1.OC1=C(C=CC=C1)CC(=O)O.CC(C)([O-])C.[K+]>>OC1=C(C=CC=C1)CC(=O)OCC1=CC=C(C=C1)OC | Cl[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:20][cH:19]1.[OH:8][C:9](=[O:10])[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[OH:18]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][C:9](=[O:10])[CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[OH:18])[cH:19][cH:20]1 | COc1ccc(CCl)cc1.O=C(O)Cc1ccccc1O | COc1ccc(COC(=O)Cc2ccccc2O)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | O=C(Cc1ccccc1)OCc1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]>>[C:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 42.3 | [{"value": 42.0, "product": "OC1=C(C=CC=C1)CC(=O)OCC1=CC=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.3, "product": "OC1=C(C=CC=C1)CC(=O)OCC1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 2-hydroxyphenylacetic acid (10 g, 66 mmol) was dissolved in N,N-dimethylformamide (100 ml) and cooled on ice-bath. Potassium tert-butoxide (8.85 g, 78 mmol) was added. The mixture was left for 30 min and allowed to reach room temperature. 4-Methoxy-benzylchloride (11.7 g, 72 mmol) in N,N-dimethylformamide (30 ml) was t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | c1ccccc1.c1ccccc1 | HCl | CN(C=O)C | null | 0.5 | COc1ccc(CCl)cc1.O=C(O)Cc1ccccc1O>CN(C=O)C>COc1ccc(COC(=O)Cc2ccccc2O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b2dfc0b229c6457b8b7e3ffde9156c9d | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.COc1ccc(COC(=O)Cc2ccccc2O)cc1>>COc1ccc(COC(=O)Cc2ccccc2OC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)cc1 | OC1=C(C=CC=C1)CC(=O)OCC1=CC=C(C=C1)OC.C1CCC(CC1)N=C=NC2CCCCC2.CN(C)C1=NC=CC=C1.C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)O>>C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OC1=C(C=CC=C1)CC(=O)OCC1=CC=C(C=C1)OC | O[C:19](=[O:20])[C@@H:21]([NH:22][C:23](=[O:24])[O:25][CH2:26][c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1)[CH:33]([CH3:34])[CH3:35].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][C:9](=[O:10])[CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[OH:18])[cH:36][cH:37]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][C:... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.COc1ccc(COC(=O)Cc2ccccc2O)cc1 | COc1ccc(COC(=O)Cc2ccccc2OC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)cc1 | null | null | ClCCl | Acylation | Mitsunobu esterification | f18451ac648b00cb7c6684a3e64bee855b0320c7eb0f62b757b29d5fb6745560 | 1489fe0065c6531b60fda87a3857d7da1cd21873868856f058c20706f927fa08 | O=C(Cc1ccccc1OC(=O)CNC(=O)OCc1ccccc1)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11] | 93.5 | [{"value": 93.0, "product": "C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OC1=C(C=CC=C1)CC(=O)OCC1=CC=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.5, "product": "C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OC1=C(C=CC=C1)CC(=O)OCC1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | null | null | null | null | 4-Methoxybenzyl 2-hydroxyphenylacetate 3 g, 11 mmol), N,N,-dichyclohexyl-carbodiimide (2.7 g, 13.2 mmol), dimethylaminopyridine (0.134 g, 1.1 mmol) and CBz-L-valine (3.3 g, 13.2 mmol) were dissolved in dichloromethane (50 ml). After the weekend the solid was filtered off, the solvent removed under reduced pressure and ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol | Ester | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | ClCCl | null | null | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.COc1ccc(COC(=O)Cc2ccccc2O)cc1>ClCCl>COc1ccc(COC(=O)Cc2ccccc2OC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2a1d1d166b4c41e98f6b104e0e2d2336 | COc1ccc(COC(=O)Cc2ccccc2OC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)cc1>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1ccccc1CC(=O)O | C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OC1=C(C=CC=C1)CC(=O)OCC1=CC=C(C=C1)OC.FC(C(=O)O)(F)F>>C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OC1=C(C=CC=C1)CC(=O)O | COc1ccc(C[O:28][C:26]([CH2:25][c:24]2[c:19]([O:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)=[O:17])[cH:20][cH:21][cH:22][cH:23]2)=[O:27])cc1>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[... | COc1ccc(COC(=O)Cc2ccccc2OC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)cc1 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1ccccc1CC(=O)O | null | null | ClCCl | Reduction | Ester saponification (alkyl deprotection) | af4a00273af84ecb3074b1842201a78a3aac9a41d2050132ad8c8c1c9d796dee | 8d997f8b7994d8c9cf23425771b3f80d4d4830ac4e3d6552f381db244a5a65c5 | O=C(CNC(=O)OCc1ccccc1)Oc1ccccc1 | C-O-c1:c:c:c(-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]):c:c:1>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 80.3 | [{"value": 80.0, "product": "C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OC1=C(C=CC=C1)CC(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.3, "product": "C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OC1=C(C=CC=C1)CC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 40 | MINUTE | 4-Methoxybenzyl 2-(N-CBz-L-valyloxy)phenylacetate (4.25 g, 8.4 mmol), was dissolved in dichloromethane (40 ml). Triflouroacetic acid (8 ml) was added with cooling on ice. The mixture was allowed to reach room temperature and stirred for 40 min. The solvent was removed under reduced pressure and the crude product was re... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Carboxylic acid | c1ccccc1 | null | c1ccccc1.c1ccccc1 | HO- | ClCCl | null | 0.666667 | COc1ccc(COC(=O)Cc2ccccc2OC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)cc1>ClCCl>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1ccccc1CC(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-949de7d1effa4335a57ffe9e3c6b70e7 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1ccccc1CC(=O)OCCl.[I-]>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1ccccc1CC(=O)OCI | C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OC1=C(C=CC=C1)CC(=O)OCCl.[Na+].[I-]>>C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OC1=C(C=CC=C1)CC(=O)OCI | Cl[CH2:29][O:28][C:26]([CH2:25][c:24]1[c:19]([O:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)=[O:17])[cH:20][cH:21][cH:22][cH:23]1)=[O:27].[I-:30]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:1... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1ccccc1CC(=O)OCCl.[I-] | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1ccccc1CC(=O)OCI | null | null | null | Functional Group Interconversion | OtherReaction | 10bee13c50a4ba107934328c21250869f883899fc8944cf8a0ebee609aa1691d | fe69d77c5ffecf9aa0236c58528d10fdb0294a434868899e60e585d0629b72f9 | O=C(CNC(=O)OCc1ccccc1)Oc1ccccc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5].[I-;H0;D0:6]>>[C:4]-[C:3](=[O;D1;H0:5])-[#8:2]-[CH2;D2;+0:1]-[I;H0;D1;+0:6] | null | [] | null | null | null | null | Chloromethyl 2-(N-CBZ-L-valyloxy)phenylacetate is treated with NaI and purified as described in the Examples above to yield the title compound.
Conditions: See reaction.notes.procedure_details.
Workup: purified | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Primary halide | null | null | c1ccccc1.c1ccccc1 | Other | null | null | null | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1ccccc1CC(=O)OCCl.[I-]>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1ccccc1CC(=O)OCI |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7608148152b84d779098fb4f6a8f574e | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1ccc(CC(=O)OCCl)cc1.[I-]>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1ccc(CC(=O)OCI)cc1 | C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OC1=CC=C(C=C1)CC(=O)OCCl.[I-].[Na+]>>C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OC1=CC=C(C=C1)CC(=O)OCI | Cl[CH2:27][O:26][C:24]([CH2:23][c:22]1[cH:21][cH:20][c:19]([O:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)=[O:17])[cH:30][cH:29]1)=[O:25].[I-:28]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:1... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1ccc(CC(=O)OCCl)cc1.[I-] | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1ccc(CC(=O)OCI)cc1 | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | 10bee13c50a4ba107934328c21250869f883899fc8944cf8a0ebee609aa1691d | fe69d77c5ffecf9aa0236c58528d10fdb0294a434868899e60e585d0629b72f9 | O=C(CNC(=O)OCc1ccccc1)Oc1ccccc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5].[I-;H0;D0:6]>>[C:4]-[C:3](=[O;D1;H0:5])-[#8:2]-[CH2;D2;+0:1]-[I;H0;D1;+0:6] | 80.1 | [{"value": 80.0, "product": "C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OC1=CC=C(C=C1)CC(=O)OCI", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.1, "product": "C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OC1=CC=C(C=C1)CC(=O)OCI", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Chloromethyl 4-(N-CBZ-L-valyloxy)phenylacetate (0.83 g, 1.9 mmol) and sodium iodide (1.15 g, 7.6 mmol) were heated in acetonitril (45 ml) for 5 h. The mixture was filtrated, the solvent removed, taken up in dichloromethane and filtrated again. Evaporation and purification by chromatography (ether-hexane, 2:3) yielded t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Primary halide | null | null | c1ccccc1.c1ccccc1 | Other | C(C)#N | null | null | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1ccc(CC(=O)OCCl)cc1.[I-]>C(C)#N>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1ccc(CC(=O)OCI)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b1f474890e4a4967a4873bd30108ba7b | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCc1ccc(C(=O)O)cc1.ClCI>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCc1ccc(C(=O)OCCl)cc1 | ICCl.C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OCCC1=CC=C(C(=O)O)C=C1.[OH-].C(CCC)[N+](CCCC)(CCCC)CCCC>>C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OCCC1=CC=C(C(=O)OCCl)C=C1 | [CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O:18][CH2:19][CH2:20][c:21]1[cH:22][cH:23][c:24]([C:25](=[O:26])[OH:27])[cH:30][cH:31]1.I[CH2:28][Cl:29]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCc1ccc(C(=O)O)cc1.ClCI | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCc1ccc(C(=O)OCCl)cc1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2f16a3cac6d3c4085515a42267501b7a0eef68b042dbe72a334a9b3dd1458b44 | 20b23d23df2ca888376bbfdf646588e67491b315935b071cb9ba310488e4ee8f | O=C(CNC(=O)OCc1ccccc1)OCCc1ccccc1 | I-[CH2;D2;+0:1]-[Cl;D1;H0:2].[O;D1;H0:3]=[C:4](-[OH;D1;+0:5])-[c:6]>>[Cl;D1;H0:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[C:4](=[O;D1;H0:3])-[c:6] | null | [] | null | null | 2 | HOUR | To a solution of 4-(2-N-benzyloxycarbonyl-L-valyloxyethyl)benzoic acid (2.0 g, 5.0 mmole) in 1,4-dioxane (20 ml)was added a 40% solution of tetrabutylammonium hydroxide (3.1 g, 4.75 mmole) and the mixture was stirred 2 hours at room temperature. The mixture was evaporated under reduced pressure and coevaporated two tim... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carboxylic acid | Primary halide.Ester | null | null | c1ccccc1.c1ccccc1 | HI | O1CCOCC1 | null | 2 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCc1ccc(C(=O)O)cc1.ClCI>O1CCOCC1>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCc1ccc(C(=O)OCCl)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9d12840f41c2495088230f709298611a | CCOC(=O)C1CCC(O)CC1.COc1ccc(CCl)cc1>>COc1ccc(COC(=O)C2CCC(O)CC2)cc1 | COC1=CC=C(CCl)C=C1.OC1CCC(CC1)C(=O)OCC.[OH-].[K+]>>OC1CCC(CC1)C(=O)OCC1=CC=C(C=C1)OC | CC[O:8][C:9](=[O:10])[CH:11]1[CH2:12][CH2:13][CH:14]([OH:15])[CH2:16][CH2:17]1.Cl[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:19][cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][C:9](=[O:10])[CH:11]2[CH2:12][CH2:13][CH:14]([OH:15])[CH2:16][CH2:17]2)[cH:18][cH:19]1 | CCOC(=O)C1CCC(O)CC1.COc1ccc(CCl)cc1 | COc1ccc(COC(=O)C2CCC(O)CC2)cc1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 159720cebf7e6166f5c8ba53526145c1ecadb9f37dd9d8f17cd0da6f6463d5a2 | 6007d70cc3173f3039a472489995dad2781e8d749be1f1aa209b0bf2f190a4b4 | O=C(OCc1ccccc1)C1CCCCC1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].Cl-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[C:3]-[C:2](=[O;D1;H0:4])-[O;H0;D2;+0:1]-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | 70 | CELSIUS | 6 | HOUR | To a solution of ethyl 4-hydroxycyclohexanoate (8.61 g, 50 mmole) in 50 ml ethanol was added a solution of potassium hydroxide 85% (3.63 g, 55 mmole) and the mixture was stirred for 6 hours at 70° C. The mixture was evaporated under reduced pressure, coevaporated two times with N,N-dimethylformamide and reduced to abou... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | null | null | c1ccccc1.C1CCCCC1 | HCl | C(C)O | 70 | 6 | CCOC(=O)C1CCC(O)CC1.COc1ccc(CCl)cc1>C(C)O>COc1ccc(COC(=O)C2CCC(O)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ea904dee533e4d0f807493821a2f3c37 | COc1ccc(COC(=O)C2CCC(OC(=O)[C@@H](NC(=O)OCc3ccccc3)C(C)C)CC2)cc1>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OC1CCC(C(=O)O)CC1 | C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OC1CCC(CC1)C(=O)OCC1=CC=C(C=C1)OC.FC(C(=O)O)(F)F>>C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OC1CCC(CC1)C(=O)O | COc1ccc(C[O:25][C:23]([CH:22]2[CH2:21][CH2:20][CH:19]([O:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)=[O:17])[CH2:27][CH2:26]2)=[O:24])cc1>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:... | COc1ccc(COC(=O)C2CCC(OC(=O)[C@@H](NC(=O)OCc3ccccc3)C(C)C)CC2)cc1 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OC1CCC(C(=O)O)CC1 | null | null | ClCCl | Reduction | Ester saponification (alkyl deprotection) | af4a00273af84ecb3074b1842201a78a3aac9a41d2050132ad8c8c1c9d796dee | 8d997f8b7994d8c9cf23425771b3f80d4d4830ac4e3d6552f381db244a5a65c5 | O=C(CNC(=O)OCc1ccccc1)OC1CCCCC1 | C-O-c1:c:c:c(-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]):c:c:1>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | 3 | HOUR | To a solution of 4-methoxybenzyl 4-(N-benzyloxycarbonyl-L-valyloxy)cyclohexanoate (12 g, 24.1 mmole) in dichloromethane (100 ml) was added trifluoroacetic acid (20 ml) and the mixture was stirred for 3 hours at room temperature. The solution was evaporated under reduced pressure and coevaporated two times with toluene.... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Carboxylic acid | c1ccccc1 | null | c1ccccc1.C1CCCCC1 | HO- | ClCCl | null | 3 | COc1ccc(COC(=O)C2CCC(OC(=O)[C@@H](NC(=O)OCc3ccccc3)C(C)C)CC2)cc1>ClCCl>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OC1CCC(C(=O)O)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b9c9d1ce89cf4d4fbc8fd22e5ac47023 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OC1CCC(C(=O)O)CC1.ClCI>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OC1CCC(C(=O)OCCl)CC1 | ICCl.C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OC1CCC(CC1)C(=O)O.[OH-].C(CCC)[N+](CCCC)(CCCC)CCCC>>C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OC1CCC(CC1)C(=O)OCCl | [CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O:18][CH:19]1[CH2:20][CH2:21][CH:22]([C:23](=[O:24])[OH:25])[CH2:28][CH2:29]1.I[CH2:26][Cl:27]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OC1CCC(C(=O)O)CC1.ClCI | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OC1CCC(C(=O)OCCl)CC1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2f16a3cac6d3c4085515a42267501b7a0eef68b042dbe72a334a9b3dd1458b44 | 20b23d23df2ca888376bbfdf646588e67491b315935b071cb9ba310488e4ee8f | O=C(CNC(=O)OCc1ccccc1)OC1CCCCC1 | I-[CH2;D2;+0:1]-[Cl;D1;H0:2].[C:3]-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6]>>[C:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[Cl;D1;H0:2] | null | [] | null | null | 2 | HOUR | To a solution of 4-(N-benzyloxycarbonyl-L-valyloxy) cyclohexanoic acid (6.6 g, 20 mmole) in 1,4-dioxane (70 ml) was added a 40% solution of tetrabutylammonium hydroxide (11.34 g, 17.5 mmole) and the mixture was stirred 2 hours at room temperature. The mixture was evaporated under reduced pressure and co-evaporated two ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carboxylic acid | Primary halide.Ester | null | null | c1ccccc1.C1CCCCC1 | HI | O1CCOCC1 | null | 2 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OC1CCC(C(=O)O)CC1.ClCI>O1CCOCC1>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OC1CCC(C(=O)OCCl)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-eebfa6f8744647d9bd9124e53f6b80f5 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OC1CCC(C(=O)OCCl)CC1.[I-]>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OC1CCC(C(=O)OCI)CC1 | C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OC1CCC(CC1)C(=O)OCCl.[I-].[Na+]>>C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OC1CCC(CC1)C(=O)OCI | Cl[CH2:26][O:25][C:23]([CH:22]1[CH2:21][CH2:20][CH:19]([O:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)=[O:17])[CH2:29][CH2:28]1)=[O:24].[I-:27]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OC1CCC(C(=O)OCCl)CC1.[I-] | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OC1CCC(C(=O)OCI)CC1 | null | null | CC(=O)C | Functional Group Interconversion | OtherReaction | 10bee13c50a4ba107934328c21250869f883899fc8944cf8a0ebee609aa1691d | fe69d77c5ffecf9aa0236c58528d10fdb0294a434868899e60e585d0629b72f9 | O=C(CNC(=O)OCc1ccccc1)OC1CCCCC1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5].[I-;H0;D0:6]>>[C:4]-[C:3](=[O;D1;H0:5])-[#8:2]-[CH2;D2;+0:1]-[I;H0;D1;+0:6] | null | [] | null | null | 8 | HOUR | To a solution of chloromethyl 4-(N-benzyloxycarbonyl-L-valyloxy)-cyclohexanoate (4.0 g, 9.4 mmole) in dry acetone (50 ml) was added sodium iodide (6.3 g, 42 mmole) and the mixture was stirred overnight at room temperature. The mixture was evaporated under reduced pressure and extracted with ethyl actate water. The orga... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Primary halide | null | null | c1ccccc1.C1CCCCC1 | Other | CC(=O)C | null | 8 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OC1CCC(C(=O)OCCl)CC1.[I-]>CC(=O)C>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OC1CCC(C(=O)OCI)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-148fd3d2081f40a0ab81c04f4766a0e1 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.CCC(CC)(CO)CO>>CCC(CC)(CO)COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C | C(C)C(CO)(CC)CO.C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)O.C1(CCCCC1)N=C=NC1CCCCC1>>C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OCC(CO)(CC)CC | [OH:9][C:10](=[O:11])[C@@H:12]([NH:13][C:14](=[O:15])[O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[CH:24]([CH3:25])[CH3:26].O[CH2:8][C:3]([CH2:2][CH3:1])([CH2:4][CH3:5])[CH2:6][OH:7]>>[CH3:1][CH2:2][C:3]([CH2:4][CH3:5])([CH2:6][OH:7])[CH2:8][O:9][C:10](=[O:11])[C@@H:12]([NH:13][C:14](=[O:15])[O:16][CH2:17]... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.CCC(CC)(CO)CO | CCC(CC)(CO)COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C | null | CN(C1=CC=NC=C1)C | ClCCl | Heteroatom Alkylation and Arylation | Esterification of Carboxylic Acids | 3f9a9ace480b666da05fcfe5450d12b5c1ea5b0d435c195e1dd4bd20281604bb | dcbf04ec563ed0e9dfc79070490a028958024079a671c385858bb18cc8ec995a | c1ccccc1 | O-[CH2;D2;+0:1]-[C:2](-[C:3])(-[C:4])-[C:5].[C:6]-[C:7](=[O;D1;H0:8])-[OH;D1;+0:9]>>[C:6]-[C:7](=[O;D1;H0:8])-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2](-[C:3])(-[C:4])-[C:5] | null | [] | null | null | 2 | DAY | To a cooled solution of 2-ethyl-2-hydroxymethyl-butan-1-ol (33.1 g, 250 mmole), 4-dimethylaminopyridine (1.22 g, 10 mmole) and N-benzyloxycarbonyl-L-valine (12.6 g, 50 mmole) in 350 ml dichloromethane was added dropwise a solution of dicyclohexyl-carbodiimide (12.4 g, 60 mmole) in 50 ml dichloromethane. The mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | CN(C1=CC=NC=C1)C.ClCCl | null | 48 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.CCC(CC)(CO)CO>CN(C1=CC=NC=C1)C.ClCCl>CCC(CC)(CO)COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7d1246d3a5fe49a7859fef5a7822b97f | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)N.O=C(Cl)OCCl>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)NC(=O)OCCl | NC(COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)(C)C.N1=CC=CC=C1.ClC(=O)OCCl>>ClCOC(=O)NC(COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)(C)C | [CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O:18][CH2:19][C:20]([CH3:21])([CH3:22])[NH2:23].Cl[C:24](=[O:25])[O:26][CH2:27][Cl:28]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16]... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)N.O=C(Cl)OCCl | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)NC(=O)OCCl | null | null | ClCCl | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]-[C:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[NH2;D1;+0:9]>>[C:5]-[C:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4] | null | [] | null | null | 3 | HOUR | To a solution of 2-amino-2-methyl-1-(N-benzyloxycarbonyl-L-valyloxy)-propane (2.9 g, 9 mmole) and pyridine (2 ml) in dichloromethane (50 ml) was added chloromethyl chloroformate(1.55 g, 12 mmole) and the mixture was stirred for 3 hours at room temperature. The mixture was evaporated under reduced pressure and ethyl ace... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccccc1 | HCl | ClCCl | null | 3 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)N.O=C(Cl)OCCl>ClCCl>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)NC(=O)OCCl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f28d440a594445d4b0e29dfdde2a7baa | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)NC(=O)OCCl.[I-]>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)NC(=O)OCI | ClCOC(=O)NC(COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)(C)C.[I-].[Na+]>>ICOC(=O)NC(COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)(C)C | Cl[CH2:27][O:26][C:24]([NH:23][C:20]([CH2:19][O:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)=[O:17])([CH3:21])[CH3:22])=[O:25].[I-:28]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)NC(=O)OCCl.[I-] | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)NC(=O)OCI | null | null | CC(=O)C | Functional Group Interconversion | OtherReaction | ae95b7ce8f8a90e5eebebe26f268c29c069f7ae68b7a932c1b0ef0abce7eceb8 | e0262737f717563a26e69fddaa33db3e2aa0a1dbbce66e7c19184ed68a5e5ada | c1ccccc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3](-[#7:4])=[O;D1;H0:5].[I-;H0;D0:6]>>[#7:4]-[C:3](=[O;D1;H0:5])-[#8:2]-[CH2;D2;+0:1]-[I;H0;D1;+0:6] | null | [] | null | null | 36 | HOUR | To a solution of 2-(N-(chloromethoxycarbonyl)-amino)-2-methyl-1-(N-benzyloxycarbonyl-L-valyloxy)propane (1.05 g, 2.53 mmole) in dry acetone (20 ml) was added sodium iodide (1.8 g, 12 mmole) and the mixture was stirred for 36 hours at room temperature. The mixture was evaporated under reduced pressure and ethyl acetate ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Primary halide | null | null | c1ccccc1 | Other | CC(=O)C | null | 36 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)NC(=O)OCCl.[I-]>CC(=O)C>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(C)(C)NC(=O)OCI |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f1bfc1bbd53e4502bb8a5a2ecf296c94 | COc1ccc(CCl)cc1.O=C(O)c1ccc(O)nc1>>COc1ccc(COC(=O)c2ccc(=O)[nH]c2)cc1 | COC1=CC=C(CCl)C=C1.OC1=NC=C(C(=O)O)C=C1.CC(C)([O-])C.[K+]>>COC1=CC=C(COC(=O)C2=CNC(C=C2)=O)C=C1 | Cl[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:19][cH:18]1.[OH:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([OH:15])[n:16][cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14](=[O:15])[nH:16][cH:17]2)[cH:18][cH:19]1 | COc1ccc(CCl)cc1.O=C(O)c1ccc(O)nc1 | COc1ccc(COC(=O)c2ccc(=O)[nH]c2)cc1 | null | null | CN(C)C=O | Acylation | OtherReaction | 4fb23717fb723486b8e9376e4f8ad6c61642c5ba6d63edb3bca1a8a61333446f | 3a7b461c445389971d866059c143d2fad456b02cecb66617acf4ceb2fda303df | O=C(OCc1ccccc1)c1ccc(=O)[nH]c1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6](-[OH;D1;+0:7])-[c:8]1:[c:9]:[c:10]:[c;H0;D3;+0:11](-[OH;D1;+0:12]):[n;H0;D2;+0:13]:[c:14]:1>>[O;D1;H0:5]=[C:6](-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[c:8]1:[c:9]:[c:10]:[c;H0;D3;+0:11](=[O;H0;D1;+0:12]):[nH;D2;+0:13]:[c:14]:1 | 48.6 | [{"value": 48.6, "product": "COC1=CC=C(COC(=O)C2=CNC(C=C2)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 1 | HOUR | To a solution of 6-hydroxynicotinic acid (4.87 g, 35 mmol) in DMF (100 mL) at room temperature, was added potassium tert-butoxide (3.93 g, 35 mmol). The reaction mixture was stirred at 60° C. for 1 h. 4-Methoxybenzylchloride (8.30 g, 53 mmol) was added and the reaction mixture was stirred at 60° C. for 4 h. The DMF was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid.Aromatic alcohol | Ester | c1ccncc1 | c1cccnc1 | c1ccccc1.c1cccnc1 | HCl | CN(C)C=O | 60 | 1 | COc1ccc(CCl)cc1.O=C(O)c1ccc(O)nc1>CN(C)C=O>COc1ccc(COC(=O)c2ccc(=O)[nH]c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ecce1927c95d42dab8d8a8a497f449ad | COc1ccc(COC(=O)c2ccc(=O)[nH]c2)cc1.OCCBr>>COc1ccc(COC(=O)c2ccc(=O)n(CCO)c2)cc1 | COC1=CC=C(COC(=O)C2=CNC(C=C2)=O)C=C1.C(=O)([O-])[O-].[K+].[K+].BrCCO>>COC1=CC=C(COC(=O)C2=CN(C(C=C2)=O)CCO)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14](=[O:15])[nH:16][cH:20]2)[cH:21][cH:22]1.Br[CH2:17][CH2:18][OH:19]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14](=[O:15])[n:16]([CH2:17][CH2:18][OH:19])[cH:20]2)[cH:21][cH:22]1 | COc1ccc(COC(=O)c2ccc(=O)[nH]c2)cc1.OCCBr | COc1ccc(COC(=O)c2ccc(=O)n(CCO)c2)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 63a13d77f5d9f4813bc1b2b9a5015f57257f9cd754c67cc86ce1c9d958dfe9d3 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=C(OCc1ccccc1)c1ccc(=O)[nH]c1 | Br-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3].[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8]:[nH;D2;+0:9]:[c:10](=[O;D1;H0:11]):[c:12]>>[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8]:[n;H0;D3;+0:9](-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3]):[c:10](=[O;D1;H0:11]):[c:12] | 79.6 | [{"value": 79.6, "product": "COC1=CC=C(COC(=O)C2=CN(C(C=C2)=O)CCO)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 6-oxo-1,6-dihydro-pyridine-3-carboxylic acid 4-methoxybenzyl ester (4.41 g, 17 mmol) and K2CO3 (2.58 g, 18.7 mmol) in DMF (100 mL) at room temperature, was added 2-bromoethanol (2.02 g, 16.2 mmol). The reaction mixture was stirred at 80° C. for 30 h, whereupon the DMF was evaporated under vacuum. The c... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cccnc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | HBr | CN(C)C=O | null | null | COc1ccc(COC(=O)c2ccc(=O)[nH]c2)cc1.OCCBr>CN(C)C=O>COc1ccc(COC(=O)c2ccc(=O)n(CCO)c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1b392be574854eb89473495727cb5b14 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.COc1ccc(COC(=O)c2ccc(=O)n(CCO)c2)cc1>>COc1ccc(COC(=O)c2ccc(=O)n(CCOC(=O)[C@@H](NC(=O)OCc3ccccc3)C(C)C)c2)cc1 | C1CCC(CC1)N=C=NC2CCCCC2.C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)O.COC1=CC=C(COC(=O)C2=CN(C(C=C2)=O)CCO)C=C1>>COC1=CC=C(COC(=O)C2=CN(C(C=C2)=O)CCOC([C@@H](NC(=O)OCC2=CC=CC=C2)C(C)C)=O)C=C1 | O[C:20](=[O:21])[C@@H:22]([NH:23][C:24](=[O:25])[O:26][CH2:27][c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1)[CH:34]([CH3:35])[CH3:36].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14](=[O:15])[n:16]([CH2:17][CH2:18][OH:19])[cH:37]2)[cH:38][cH:39]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.COc1ccc(COC(=O)c2ccc(=O)n(CCO)c2)cc1 | COc1ccc(COC(=O)c2ccc(=O)n(CCOC(=O)[C@@H](NC(=O)OCc3ccccc3)C(C)C)c2)cc1 | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Acylation | Esterification of Carboxylic Acids | d9bd78214ee7dbc907e499722ae01849a72d188753963443e5df9fe42c31c43b | 3652e761944e8ef7ee40675a156c8ae39909c72166786934d88652debf2ec1ac | O=C(CNC(=O)OCc1ccccc1)OCCn1cc(C(=O)OCc2ccccc2)ccc1=O | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[C:9]-[OH;D1;+0:10]>>[C:8]-[C:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7] | 52.9 | [{"value": 52.9, "product": "COC1=CC=C(COC(=O)C2=CN(C(C=C2)=O)CCOC([C@@H](NC(=O)OCC2=CC=CC=C2)C(C)C)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a mixture of DCC (5.06 g, 24.5 mmol), DMAP (318 mg, 2.6 mmol) and N-CBz-L-valine (6.48 g, 25.8 mmol) in CH2Cl2 (200 mL) at 0° C., was added dropwise a solution of 1-(2-hydroxyethyl)-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid 4-methoxybenzyl ester (6.40 g, 24 mmol) in CH2Cl2 (200 mL). After 1 h at 0° C., the temper... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1.c1ccncc1.c1ccccc1 | HO- | CN(C)C=1C=CN=CC1.C(Cl)Cl | null | 1 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.COc1ccc(COC(=O)c2ccc(=O)n(CCO)c2)cc1>CN(C)C=1C=CN=CC1.C(Cl)Cl>COc1ccc(COC(=O)c2ccc(=O)n(CCOC(=O)[C@@H](NC(=O)OCc3ccccc3)C(C)C)c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-64999eba73344140b1252812f44546db | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCn1cc(C(=O)OCCl)ccc1=O.[I-]>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCn1cc(C(=O)OCI)ccc1=O | ClCOC(=O)C1=CN(C(C=C1)=O)CCOC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O.[I-].[Na+]>>ICOC(=O)C1=CN(C(C=C1)=O)CCOC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O | Cl[CH2:27][O:26][C:24]([c:23]1[cH:22][n:21]([CH2:20][CH2:19][O:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)=[O:17])[c:31](=[O:32])[cH:30][cH:29]1)=[O:25].[I-:28]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCn1cc(C(=O)OCCl)ccc1=O.[I-] | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCn1cc(C(=O)OCI)ccc1=O | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | 10bee13c50a4ba107934328c21250869f883899fc8944cf8a0ebee609aa1691d | fe69d77c5ffecf9aa0236c58528d10fdb0294a434868899e60e585d0629b72f9 | O=C(CNC(=O)OCc1ccccc1)OCCn1ccccc1=O | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]:[#7;a:7].[I-;H0;D0:8]>>[#7;a:7]:[c:6]:[c:5]-[C:3](=[O;D1;H0:4])-[#8:2]-[CH2;D2;+0:1]-[I;H0;D1;+0:8] | 94.7 | [{"value": 94.7, "product": "ICOC(=O)C1=CN(C(C=C1)=O)CCOC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 4 | HOUR | To a solution of 1-(2-N-CBz-L-valyloxyethyl)-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid chloromethyl ester (1.80 g, 3.87 mmol) in acetonitrile (30 mL), was added sodium iodide (2.32 g, 15.5 mmol). The solution was stirred for 4 h at 60° C. The resulting suspension was filtered and the filtrate was evaporated. The res... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Primary halide | null | null | c1ccccc1.c1ccncc1 | Other | C(C)#N | 60 | 4 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCn1cc(C(=O)OCCl)ccc1=O.[I-]>C(C)#N>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCn1cc(C(=O)OCI)ccc1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0f1e0aa8ae024949b3da1e0337cecb11 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCc1ccc(C=O)o1>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCc1ccc(C(=O)O)o1 | [O-]Cl=O.[Na+].C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OCC1=CC=C(O1)C=O.C(=O)(O)[O-].[Na+]>>C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OCC1=CC=C(O1)C(=O)O | [CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O:18][CH2:19][c:20]1[cH:21][cH:22][c:23]([CH:24]=[O:25])[o:27]1>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O:18][CH2:19]... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCc1ccc(C=O)o1 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCc1ccc(C(=O)O)o1 | null | null | O.CC#N | Oxidation | Oxidation of aldehydes to carboxylic acids | 53d556378d4cb30c33d50a2e1886f8fba4abcbb7065d1faceeb5e5968b58008d | 2f35b69536247c389825da7241226b4e568110d1cfe736c83136d58ad1c9dae2 | O=C(CNC(=O)OCc1ccccc1)OCc1ccco1 | [O;D1;H0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[#8;a:5]:[c:6]>>[O;D1;H0:1]=[C;H0;D3;+0:2](-[O;D1;H1:7])-[c:3](:[c:4]):[#8;a:5]:[c:6] | 34 | [{"value": 34.0, "product": "C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OCC1=CC=C(O1)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | A solution of NaClO2 (2.8 mmol) in 3 mL water was added dropwise to a stirred solution of 5-[(N-benzyloxycarbonyl-L-valyloxy)methyl]-2-furaldehyde (798 mg, 2.22 mmol) from step (a) in 3 mL MeCN, with cooling in an ice bath. After 2.5 h, the ice bath was removed, 2 mL more MeCN was added, and the two-phase liquid reacti... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Carboxylic acid | null | null | c1ccccc1.c1ccoc1 | Other | O.CC#N | null | 2.5 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCc1ccc(C=O)o1>O.CC#N>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCc1ccc(C(=O)O)o1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d3926626ab4b4390a528d843239d22ee | COc1ccc(COC(=O)c2ccc(O)cc2)cc1.OCCBr>>COc1ccc(COC(=O)c2ccc(OCCO)cc2)cc1 | OC1=CC=C(C(=O)OCC2=CC=C(C=C2)OC)C=C1.C([O-])([O-])=O.[K+].[K+].BrCCO>>OCCOC1=CC=C(C(=O)OCC2=CC=C(C=C2)OC)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([OH:15])[cH:19][cH:20]2)[cH:21][cH:22]1.Br[CH2:16][CH2:17][OH:18]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([O:15][CH2:16][CH2:17][OH:18])[cH:19][cH:20]2)[cH:21][cH:22]1 | COc1ccc(COC(=O)c2ccc(O)cc2)cc1.OCCBr | COc1ccc(COC(=O)c2ccc(OCCO)cc2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(OCc1ccccc1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[O;D1;H1:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 80 | CELSIUS | 48 | HOUR | To a solution of 4-methoxybenzyl 4-hydroxybenzoate (7.0 g, 27 mmole) in dry NN-dimethylformamide (50 ml) was added potassium carbonate (4.15 g, 30 mmole) and 2-bromoethanol. The mixture was stirred 48 hours at 80° C., evaporated under reduced pressure and ethyl acetate and water were added. The organic phase was washed... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | null | 80 | 48 | COc1ccc(COC(=O)c2ccc(O)cc2)cc1.OCCBr>>COc1ccc(COC(=O)c2ccc(OCCO)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-61a76cca51a74f099b8435aaf4b84a1d | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCOc1ccc(C(=O)O)c(CI)c1>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCOc1ccc(C(=O)O)cc1 | ICC1=C(C(=O)O)C=CC(=C1)OCCOC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O.FC(C(=O)O)(F)F>>C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OCCOC1=CC=C(C(=O)O)C=C1 | IC[c:29]1[c:25]([C:26](=[O:27])[OH:28])[cH:24][cH:23][c:22]([O:21][CH2:20][CH2:19][O:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)=[O:17])[cH:30]1>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:1... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCOc1ccc(C(=O)O)c(CI)c1 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCOc1ccc(C(=O)O)cc1 | null | null | ClCCl | Miscellaneous | OtherReaction | 580dbda2d71c1ade592946b82319659b10473e14402a8d60005effee81e40ce7 | 60e0209a3e01281b77ea7e07e181a846736713b5a4a90ae8d47a0480f9ce79e5 | O=C(CNC(=O)OCc1ccccc1)OCCOc1ccccc1 | I-C-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]):[c:8]>>[O;D1;H0:6]=[C:5](-[O;D1;H1:7])-[c:4](:[c:8]):[cH;D2;+0:1]:[c:2]:[c:3] | null | [] | null | null | 3 | HOUR | To a solution of 4-methoxybenzyl 4-(2-N-benzyloxycarbonyl-L-valyloxyethoxy) benzoate (10.2 g, 19.04 mmole) in dichloromethane (100 ml) was added trifluoroacetic acid (20 ml) and the mixture was stirred 3 hours at room temperature. The solution was evaporated under reduced pressure and co-evaporated two times with tolue... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HI | ClCCl | null | 3 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCOc1ccc(C(=O)O)c(CI)c1>ClCCl>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCOc1ccc(C(=O)O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2119ae9c18764cd0b63e1aeb09c79fef | CCCCCCCCCCCCCCCCCC(=O)Cl.OCC(O)CO>>CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO | C(=O)(O)[O-].[Na+].OCC(O)CO.N1=CC=CC=C1.C(CCCCCCCCCCCCCCCCC)(=O)Cl>>C(CCCCCCCCCCCCCCCCC)(=O)OCC(O)CO | Cl[C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19].[OH:20][CH2:21][CH:22]([OH:23])[CH2:24][OH:25]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]... | CCCCCCCCCCCCCCCCCC(=O)Cl.OCC(O)CO | CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO | null | null | CN(C)C=O | Acylation | Schotten-Baumann to ester | 6cefe709828c5bd4655f254e75d5dff9e8876e192e7dd47256c1bc0067bc5291 | d8a7643b81ed07a6f633aa99465180dfa0565e61ae25aef36338ebb9837c9cef | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6]-[C:5] | null | [] | null | null | null | null | To a mixture of glycerol (30 g, 326 mmol) and pyridine (25 ml) dissolved in DMF (300 ml) was added dropwise stearoyl chloride (10 g, 33 mmol) dissolved in DMF 100 ml9. The mixture was cooled on an ice bath until addition was complete, whereupon the reaction was maintained under an N2 atmosphere overnight. After 15 hour... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ester | null | null | null | HCl | CN(C)C=O | null | null | CCCCCCCCCCCCCCCCCC(=O)Cl.OCC(O)CO>CN(C)C=O>CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e586d689a95a4d88aef4134ac987ac55 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.OCC(O)CO>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(O)CO | CCOC(=O)C.CCCCCC.C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)O.OCC(O)CO.C1(CCCCC1)N=C=NC1CCCCC1>>C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCC(O)CO | [CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[OH:18].O[CH2:19][CH:20]([OH:21])[CH2:22][OH:23]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O:18][CH2:19][CH:20]([OH:21])... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.OCC(O)CO | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(O)CO | null | CN(C1=CC=NC=C1)C | C(Cl)Cl.CO | Heteroatom Alkylation and Arylation | Esterification of Carboxylic Acids | 3f9a9ace480b666da05fcfe5450d12b5c1ea5b0d435c195e1dd4bd20281604bb | dcbf04ec563ed0e9dfc79070490a028958024079a671c385858bb18cc8ec995a | c1ccccc1 | O-[CH2;D2;+0:1]-[C:2](-[C:3])-[O;D1;H1:4].[C:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]>>[C:3]-[C:2](-[O;D1;H1:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[C:6](-[C:5])=[O;D1;H0:7] | null | [] | null | null | 8 | HOUR | CBz-L-valine (4.35 g, 17.3 mmol) was added to a fivefold excess of glycerol (8 ml, 86.9 mmol) togehter with dicyclohexylcarbodiimide (4.29 g 20.8 mmol) and 4-dimethylaminopyridine (0.212 g) at room temperature. After stirring overnight the suspension was filtered and DMF removed in vacuo from the filtrate. The residue ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | CN(C1=CC=NC=C1)C.C(Cl)Cl.CO | null | 8 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.OCC(O)CO>CN(C1=CC=NC=C1)C.C(Cl)Cl.CO>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(O)CO |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e16b8c466ff1470e810804f27a7337b6 | C=CCC(CO)CO.CC(C)[C@H](NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(=O)O>>C=CCC(CO)COC(=O)[C@@H](NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(C)C | C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)N[C@@H](C(C)C)C(=O)O.C(C=C)C(CO)CO.C1CCC(CC1)N=C=NC2CCCCC2>>C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCC(CO)CC=C | O[CH2:7][CH:4]([CH2:3][CH:2]=[CH2:1])[CH2:5][OH:6].[OH:8][C:9](=[O:10])[C@@H:11]([NH:12][C:13]([c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)([c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1)[c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1)[CH:32]([CH3:33])[CH3:34]>>[CH2:1]=[CH:2][CH2:3][CH:4]([CH2:5][OH:6])[CH2:7][O:8][C:9](=[O:1... | C=CCC(CO)CO.CC(C)[C@H](NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(=O)O | C=CCC(CO)COC(=O)[C@@H](NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(C)C | null | null | ClCCl | Heteroatom Alkylation and Arylation | Esterification of Carboxylic Acids | 3f9a9ace480b666da05fcfe5450d12b5c1ea5b0d435c195e1dd4bd20281604bb | dcbf04ec563ed0e9dfc79070490a028958024079a671c385858bb18cc8ec995a | c1ccc(C(c2ccccc2)c2ccccc2)cc1 | O-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]-[C:5]=[C;D1;H2:6].[C:7]-[C:8](=[O;D1;H0:9])-[OH;D1;+0:10]>>[C:7]-[C:8](=[O;D1;H0:9])-[O;H0;D2;+0:10]-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]-[C:5]=[C;D1;H2:6] | 66.1 | [{"value": 66.1, "product": "C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCC(CO)CC=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of N-trityl-L-valine (5.5 g, 15.2 mmole), 2-allyl-1,3-propandiol (4.4 g, 38 mmol), N,N-dimethylamino pyridine (183 mg, 1.5 mmol) in dichloromethane (120 ml) was added DCC (3.5 g, 16.7 mmol). The reaction was kept under reflux overnight. After filtration through Celite, the organic phase was washed with so... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | ClCCl | null | null | C=CCC(CO)CO.CC(C)[C@H](NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(=O)O>ClCCl>C=CCC(CO)COC(=O)[C@@H](NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c70d11fec038431bb2b903e3273c1921 | C=CCC(CO)COC(=O)[C@@H](NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(C)C.CCCCCCCCCCCCCCCCCC(=O)Cl>>C=CCC(COC(=O)[C@@H](NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(C)C)C(O)C(=O)CCCCCCCCCCCCCCCCC | C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCC(CO)CC=C.N1=CC=CC=C1.C(CCCCCCCCCCCCCCCCC)(=O)Cl>>C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCC(C(O)C(CCCCCCCCCCCCCCCCC)=O)CC=C | [CH2:1]=[CH:2][CH2:3][CH:4]([CH2:5][O:6][C:7](=[O:8])[C@@H:9]([NH:10][C:11]([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)([c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1)[CH:30]([CH3:31])[CH3:32])[CH2:33][OH:34].Cl[C:35](=[O:36])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2... | C=CCC(CO)COC(=O)[C@@H](NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(C)C.CCCCCCCCCCCCCCCCCC(=O)Cl | C=CCC(COC(=O)[C@@H](NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(C)C)C(O)C(=O)CCCCCCCCCCCCCCCCC | null | null | ClCCl | C-C Coupling | OtherReaction | 5ac9135a616075222ae2bd2bf80f3c8f4e98906452b1ab55b7c85868426c4f24 | 9d7d081a39a6ca8d70a2009dc1d8b908362657793027d71dc67bbd4818a3fdaf | c1ccc(C(c2ccccc2)c2ccccc2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6](-[C:7]-[C:8]=[C;D1;H2:9])-[CH2;D2;+0:10]-[O;D1;H1:11]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:10](-[O;D1;H1:11])-[C:6](-[C:5])-[C:7]-[C:8]=[C;D1;H2:9] | null | [] | null | null | 3 | HOUR | To a solution of 1-O-(N-trityl-L-valyl)-2-allyl-1,3-propandiol (1.83 g, 4 mmol) in dichloromethane (40 ml) and pyridine (3.2 ml, 40 mmol) at 0° C. was added dropwise stearoyl chloride (3.62 g, 12 mmol) in dichloromethane. The solution was warmed up to room temperature, and kept for 3 hr. It was then washed with sodium ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ketone | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | ClCCl | null | 3 | C=CCC(CO)COC(=O)[C@@H](NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(C)C.CCCCCCCCCCCCCCCCCC(=O)Cl>ClCCl>C=CCC(COC(=O)[C@@H](NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(C)C)C(O)C(=O)CCCCCCCCCCCCCCCCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2a1842918cfe48009ac4bd036a2c86d6 | CCCCCCCCCCCCCCCCCC(=O)OCC(CCCC(=O)O)COC(=O)[C@@H](NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(C)C.Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](CO)O2)c(=O)[nH]1>>CCCCCCCCCCCCCCCCCC(=O)OCC(CCCC(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F)COC(=O)[C@@H](NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(C)C | C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCC(CCCC(=O)O)COC(CCCCCCCCCCCCCCCCC)=O.F[C@H]1C[C@@H](O[C@@H]1CO)N1C=NC=2C(=O)NC(N)=NC12.CN(C)C1=NC=CC=C1.C1CCC(CC1)N=C=NC2CCCCC2>>F[C@H]1C[C@@H](O[C@@H]1COC(CCCC(COC(CCCCCCCCCCCCCCCCC)=O)COC([C@@H](NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C(C)C)=O)=O)N1C=NC=2C(... | O[C:26]([CH2:25][CH2:24][CH2:23][CH:22]([CH2:21][O:20][C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19])[CH2:47][O:48][C:49](=[O:50])[C@@H:51]([NH:52][C:53]([c:54]1[cH:55][cH:56][cH:57][cH:58][cH:59]1)([c:60]1[cH:61][cH:62][cH:... | CCCCCCCCCCCCCCCCCC(=O)OCC(CCCC(=O)O)COC(=O)[C@@H](NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(C)C.Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](CO)O2)c(=O)[nH]1 | CCCCCCCCCCCCCCCCCC(=O)OCC(CCCC(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F)COC(=O)[C@@H](NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(C)C | null | null | CN(C)C=O | Acylation | Esterification of Carboxylic Acids | d9bd78214ee7dbc907e499722ae01849a72d188753963443e5df9fe42c31c43b | 3652e761944e8ef7ee40675a156c8ae39909c72166786934d88652debf2ec1ac | O=C(CCCCCOC(=O)CNC(c1ccccc1)(c1ccccc1)c1ccccc1)OC[C@@H]1CC[C@H](n2cnc3c(=O)[nH]cnc32)O1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#8:5]-[C:6]-[C:7]-[OH;D1;+0:8]>>[#8:5]-[C:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | null | [] | null | null | 8 | HOUR | To a solution of 5-(N-trityl-L-valyloxymethyl)-6-stearoyloxyhexanoic acid (462 mg, 0.6 mmole) and 2′,3′-dideoxy-3′-fluoroguanosine (340 mg, 1.25 mmol) in DMF (3 ml) were added dimethylaminopyridine (7 mg, 0.06 mmole), and DCC (136 mg, 0.66 mmol). The reaction was kept at room temperature overnight, and then at 40° C. f... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | C1CCOC1.c1ncc2nc[nH]c2n1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | CN(C)C=O | null | 8 | CCCCCCCCCCCCCCCCCC(=O)OCC(CCCC(=O)O)COC(=O)[C@@H](NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(C)C.Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](CO)O2)c(=O)[nH]1>CN(C)C=O>CCCCCCCCCCCCCCCCCC(=O)OCC(CCCC(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F)COC(=O)[C@@H](NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-32517237895842ce8fc59a8f6772d81c | CCCCCCCCCCCCCCCCCC(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(=O)O.Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](CO)O2)c(=O)[nH]1>>CCCCCCCCCCCCCCCCCC(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F | F[C@H]1C[C@@H](O[C@@H]1CO)N1C=NC=2C(=O)NC(N)=NC12.C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OCC(CC(=O)O)COC(CCCCCCCCCCCCCCCCC)=O.CN(C)C1=NC=CC=C1.C1CCC(CC1)N=C=NC2CCCCC2>>F[C@H]1C[C@@H](O[C@@H]1COC(CC(COC(CCCCCCCCCCCCCCCCC)=O)COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)=O)N1C=NC=2C(=O)NC(N)=NC12 | O[C:43]([CH2:42][CH:22]([CH2:21][O:20][C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19])[CH2:23][O:24][C:25](=[O:26])[C@@H:27]([NH:28][C:29](=[O:30])[O:31][CH2:32][c:33]1[cH:34][cH:35][cH:36][cH:37][cH:38]1)[CH:39]([CH3:40])[CH... | CCCCCCCCCCCCCCCCCC(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(=O)O.Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](CO)O2)c(=O)[nH]1 | CCCCCCCCCCCCCCCCCC(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F | null | C(C)(=O)O | ClCCl.CN(C)C=O | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | O=C(CCCOC(=O)CNC(=O)OCc1ccccc1)OC[C@@H]1CC[C@H](n2cnc3c(=O)[nH]cnc32)O1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#8:5]-[C:6]-[C:7]-[OH;D1;+0:8]>>[#8:5]-[C:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | null | [] | null | null | 2 | DAY | To a solution of 2′,3′-dideoxy-3′-fluoroguanosine (113 mg, 0.42 mmol) and 3-(N-benzyloxycarbonyl-L-valyloxymethyl)-4-stearoyloxy-butyric acid (140 mg, 0.21 mmol) in DMF (2 ml) were added dimethylaminopyridine (3 mg, 0.02 mmol) and DCC (52 mg, 0.25 mmol). After two days, dichloromethane (10 ml) and a few drops of acetic... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1.C1CCOC1.c1ncc2nc[nH]c2n1 | HO- | C(C)(=O)O.ClCCl.CN(C)C=O | null | 48 | CCCCCCCCCCCCCCCCCC(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(=O)O.Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](CO)O2)c(=O)[nH]1>C(C)(=O)O.ClCCl.CN(C)C=O>CCCCCCCCCCCCCCCCCC(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-af17f8c318544e7da024f3bc7e2d6950 | O=C(C[P+](c1ccccc1)(c1ccccc1)c1ccccc1)OCc1ccccc1.O=CC(O)CO>>O=C(C=CC(O)CO)OCc1ccccc1 | C(C(C=O)O)O.[Br-].C(C1=CC=CC=C1)OC(=O)C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>OC(C=CC(=O)OCC1=CC=CC=C1)CO | c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:3][C:2](=[O:1])[O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)cc1.O=[CH:4][CH:5]([OH:6])[CH2:7][OH:8]>>[O:1]=[C:2]([CH:3]=[CH:4][CH:5]([OH:6])[CH2:7][OH:8])[O:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | O=C(C[P+](c1ccccc1)(c1ccccc1)c1ccccc1)OCc1ccccc1.O=CC(O)CO | O=C(C=CC(O)CO)OCc1ccccc1 | null | null | O1CC1CC | C-C Coupling | Wittig with Phosphonium | 71bd2654cede51545adee465eb47bf49794d5c57afe21c7fb122478c5a700139 | 203dd34a20dceaf1737adbf20e01b43c2424e4e4b1722d942d1a796d895396e6 | c1ccccc1 | O=[CH;D2;+0:1]-[C:2](-[C:3])-[O;D1;H1:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH;D2;+0:9]=[CH;D2;+0:1]-[C:2](-[C:3])-[O;D1;H1:4] | null | [] | null | null | null | null | A mixture of DL-glycerinaldehyde (4,5 g, 50 mmole) and (benzyloxycarbonylmethyl)-triphenyl-phosphoniumbromide (24.57 g, 50 mmole) in 100 ml 1,2-epoxybutane was refluxed overnight. The mixture was evaporated under vacuum and the product was isolated by silica gel column chromatography.
Conditions: See reaction.notes.pro... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1 | HO- | O1CC1CC | null | null | O=C(C[P+](c1ccccc1)(c1ccccc1)c1ccccc1)OCc1ccccc1.O=CC(O)CO>O1CC1CC>O=C(C=CC(O)CO)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f80c3d133f74432c87ce8c6b99c782ea | CC(C)[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O.O=C(C=CC(O)CO)OCc1ccccc1>>CC(C)[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)OCC(O)C=CC(=O)OCc1ccccc1 | C1CCC(CC1)N=C=NC2CCCCC2.OC(C=CC(=O)OCC1=CC=CC=C1)CO.C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N[C@@H](C(C)C)C(=O)O>>C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N[C@@H](C(C)C)C(=O)OCC(C=CC(=O)OCC1=CC=CC=C1)O | O[C:23]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][CH:10]1[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2-[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]21)=[O:24].[OH:25][CH2:26][CH:27]([OH:28])[CH:29]=[CH:30][C:31](=[O:32])[O:33][CH2:34][c:35]1[cH:36][cH:37][cH:38][cH:39][cH:40]1>>[CH3:1][CH:2]([CH3:3])[C@H:... | CC(C)[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O.O=C(C=CC(O)CO)OCc1ccccc1 | CC(C)[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)OCC(O)C=CC(=O)OCc1ccccc1 | null | CN(C)C=1C=CN=CC1 | ClCCl | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | O=C(C=CCCOC(=O)CNC(=O)OCC1c2ccccc2-c2ccccc21)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]=[C:9]-[C:10]-[C:11]-[OH;D1;+0:12]>>[C:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:12]-[C:11]-[C:10]-[C:9]=[C:8] | null | [] | 10 | CELSIUS | 8 | HOUR | A mixture of benzyl 4,5-dihydroxy-2-pentenoate (4.4 g, 20 mmole), N-FMOC-L-valine (5.8 g, 17 mmole) and DMAP (0.21 g, 1,7 mmole) in 100 ml dichloromethane was cooled to about 10° C. A solution of DCC (4.2 g, 20 mmole) in 25 ml dichloromethane was added droppwise at the same temperature and the mixture was stirred overn... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1.c1ccc2c(c1)Cc1ccccc12 | HO- | CN(C)C=1C=CN=CC1.ClCCl | 10 | 8 | CC(C)[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O.O=C(C=CC(O)CO)OCc1ccccc1>CN(C)C=1C=CN=CC1.ClCCl>CC(C)[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)OCC(O)C=CC(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c1c6dcb0cabd47099b26abcaaa5aef7d | CC(C)[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)OCC(O)C=CC(=O)OCc1ccccc1.CCCCCCCCCCCCCCCCCC(=O)Cl>>CCCCCCCCCCCCCCCCCC(=O)OC(C=CC(=O)OCc1ccccc1)COC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C | C(O)([O-])=O.[Na+].C(C1=CC=CC=C1)OC(C=CC(COC([C@@H](NC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C12)C(C)C)=O)O)=O.N1=CC=CC=C1.C(CCCCCCCCCCCCCCCCC)(=O)Cl>>C(C1=CC=CC=C1)OC(C=CC(COC([C@@H](NC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C12)C(C)C)=O)OC(CCCCCCCCCCCCCCCCC)=O)=O | [OH:20][CH:21]([CH:22]=[CH:23][C:24](=[O:25])[O:26][CH2:27][c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1)[CH2:34][O:35][C:36](=[O:37])[C@@H:38]([NH:39][C:40](=[O:41])[O:42][CH2:43][CH:44]1[c:45]2[cH:46][cH:47][cH:48][cH:49][c:50]2-[c:51]2[cH:52][cH:53][cH:54][cH:55][c:56]21)[CH:57]([CH3:58])[CH3:59].Cl[C:18]([CH2:17][CH2... | CC(C)[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)OCC(O)C=CC(=O)OCc1ccccc1.CCCCCCCCCCCCCCCCCC(=O)Cl | CCCCCCCCCCCCCCCCCC(=O)OC(C=CC(=O)OCc1ccccc1)COC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C | null | null | ClCCl | Protection | Schotten-Baumann to ester | 0ff6f452f545c5714d297592668645b2f1aab4c7ba249a3331b014e41dc6881c | 96f6d8bed38830913bc384a75a5a9e04ad1b99b6be7c7e9d85b6ecc9049f5127 | O=C(C=CCCOC(=O)CNC(=O)OCC1c2ccccc2-c2ccccc21)OCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]=[C:9]-[C:10](-[C:11])-[OH;D1;+0:12]>>[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]=[C:9]-[C:10](-[C:11])-[O;H0;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | null | [] | null | null | 8 | HOUR | To a solution of benzyl-5-(N-FMOC-L-valyloxy)-4-hydroxy-2-pentenoate (6.5 g, 12 mmol) and pyridine (2.0 g, 25 mmole) in 100 ml dichloromethane at 10° C. was added dropwise a solution of stearoylchloride (4.55 g, 15 mmol) in 25 ml dichloromethane. The mixture was stirred overnight. 100 ml of 5% sodium hydrogencarbonate ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary alcohol | Ester | null | null | c1ccccc1.c1ccc2c(c1)Cc1ccccc12 | HCl | ClCCl | null | 8 | CC(C)[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)OCC(O)C=CC(=O)OCc1ccccc1.CCCCCCCCCCCCCCCCCC(=O)Cl>ClCCl>CCCCCCCCCCCCCCCCCC(=O)OC(C=CC(=O)OCc1ccccc1)COC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9993400565da4367b8e7755ddf3bee90 | CCCCCCCCCCCCCCCCCC(=O)OC(C=CC(=O)OCc1ccccc1)COC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C>>CCCCCCCCCCCCCCCCCC(=O)OC(CCC(=O)O)COC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C | C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N[C@@H](C(C)C)C(=O)OCC(C=CC(=O)OCC1=CC=CC=C1)OC(CCCCCCCCCCCCCCCCC)=O>>C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N[C@@H](C(C)C)C(=O)OCC(CCC(=O)O)OC(CCCCCCCCCCCCCCCCC)=O | c1ccc(C[O:26][C:24]([CH:23]=[CH:22][CH:21]([O:20][C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19])[CH2:27][O:28][C:29](=[O:30])[C@@H:31]([NH:32][C:33](=[O:34])[O:35][CH2:36][CH:37]2[c:38]3[cH:39][cH:40][cH:41][cH:42][c:43]3-[c... | CCCCCCCCCCCCCCCCCC(=O)OC(C=CC(=O)OCc1ccccc1)COC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C | CCCCCCCCCCCCCCCCCC(=O)OC(CCC(=O)O)COC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C | null | [Pd] | C(C)(=O)OCC | Deprotection | OtherReaction | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2c(c1)Cc1ccccc1-2 | [C:1]-[C:2](-[#8:3]-[C:4]=[O;D1;H0:5])-[CH;D2;+0:6]=[CH;D2;+0:7]-[C:8](=[O;D1;H0:9])-[O;H0;D2;+0:10]-C-c1:c:c:c:c:c:1>>[C:1]-[C:2](-[#8:3]-[C:4]=[O;D1;H0:5])-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[OH;D1;+0:10] | null | [] | null | null | null | null | A solution of benzyl 5-(N-FMOC-L-valyloxy)-4-stearoyloxy-2-pentenoate (3.8 g, 4.69 mmole) in 50 ml ethyl acetate was hydrogenated with 10% palladium on charcoal (0,5 g) at normal pressure for five hours at room temperature. The catalyst was filtered and washed with ethyl acetate and 1,4-dioxane. The solution was evapor... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | c1ccc2c(c1)Cc1ccccc12 | Other | [Pd].C(C)(=O)OCC | null | null | CCCCCCCCCCCCCCCCCC(=O)OC(C=CC(=O)OCc1ccccc1)COC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C>[Pd].C(C)(=O)OCC>CCCCCCCCCCCCCCCCCC(=O)OC(CCC(=O)O)COC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-85f084d0247345d58a139fde43cfcc49 | CC(C)[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)OCC(O)C(=O)OCc1ccccc1.CCCCCCCCCCCCCCCCCC(=O)Cl>>CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C)C(=O)OCc1ccccc1 | C(O)([O-])=O.[Na+].C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N[C@@H](C(C)C)C(=O)OCC(C(=O)OCC1=CC=CC=C1)O.N1=CC=CC=C1.C(CCCCCCCCCCCCCCCCC)(=O)Cl>>C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N[C@@H](C(C)C)C(=O)OCC(C(=O)OCC1=CC=CC=C1)OC(CCCCCCCCCCCCCCCCC)=O | [OH:20][CH:21]([CH2:22][O:23][C:24](=[O:25])[C@@H:26]([NH:27][C:28](=[O:29])[O:30][CH2:31][CH:32]1[c:33]2[cH:34][cH:35][cH:36][cH:37][c:38]2-[c:39]2[cH:40][cH:41][cH:42][cH:43][c:44]21)[CH:45]([CH3:46])[CH3:47])[C:48](=[O:49])[O:50][CH2:51][c:52]1[cH:53][cH:54][cH:55][cH:56][cH:57]1.Cl[C:18]([CH2:17][CH2:16][CH2:15][CH... | CC(C)[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)OCC(O)C(=O)OCc1ccccc1.CCCCCCCCCCCCCCCCCC(=O)Cl | CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C)C(=O)OCc1ccccc1 | null | null | ClCCl | Acylation | Schotten-Baumann to ester | 27b76e29491fa7db5375755e15223de884a194f57a493147db0b5495ea981908 | d47ab90ace9b5dcd818151c10aae400dcf599f5a3476072b8dfedc474e97c335 | O=C(CCOC(=O)CNC(=O)OCC1c2ccccc2-c2ccccc21)OCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6](-[OH;D1;+0:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6](-[C:5])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11] | null | [] | null | null | 8 | HOUR | To a stirred solution of benzyl 3-(N-FMOC-L-valyloxy)-2-hydroxypropionate (4.6 g 8.89 mmole) and pyridine (1.41 g, 17.8 mmole) in 80 ml dichloromethane was added dropwise a solution of stearoylchloride (3.64 g, 12 mmole) in 20 ml dichloromethane and the mixture was stirred overnight at room temperature. 100 ml of 5% so... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary alcohol | Ester | null | null | c1ccccc1.c1ccc2c(c1)Cc1ccccc12 | HCl | ClCCl | null | 8 | CC(C)[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)OCC(O)C(=O)OCc1ccccc1.CCCCCCCCCCCCCCCCCC(=O)Cl>ClCCl>CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C)C(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-89dc0838a57c42a7a48e70016ce43eb6 | CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C)C(=O)OCc1ccccc1>>CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C)C(=O)O | C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N[C@@H](C(C)C)C(=O)OCC(C(=O)OCC1=CC=CC=C1)OC(CCCCCCCCCCCCCCCCC)=O>>C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N[C@@H](C(C)C)C(=O)OCC(C(=O)O)OC(CCCCCCCCCCCCCCCCC)=O | c1ccc(C[O:50][C:48]([CH:21]([O:20][C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19])[CH2:22][O:23][C:24](=[O:25])[C@@H:26]([NH:27][C:28](=[O:29])[O:30][CH2:31][CH:32]2[c:33]3[cH:34][cH:35][cH:36][cH:37][c:38]3-[c:39]3[cH:40][cH... | CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C)C(=O)OCc1ccccc1 | CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C)C(=O)O | null | [Pd] | C(C)(=O)OCC | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2c(c1)Cc1ccccc1-2 | [C:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1>>[C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4] | null | [] | null | null | null | null | A solution of benzyl 3-(N-FMOC-L-valyloxy)-2-stearoyloxypropionate (0.78 g, 1 mmole) in 20 ml ethyl acetate was hydrogenated with 10% palladium on charcoal (0.2 g) at normal pressure for three hours at room temperature. The catalyst was filtered and washed with ethyl acetate and 1,4-dioxane. The solution was evaporated... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | c1ccc2c(c1)Cc1ccccc12 | Other | [Pd].C(C)(=O)OCC | null | null | CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C)C(=O)OCc1ccccc1>[Pd].C(C)(=O)OCC>CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-442ccb9316f74d9f951f4777aea595d8 | CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>>CCCCCCCCCCCCCCCCCC(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)OC(=O)Cl | C(C)N(CC)CC.C(OC(Cl)(Cl)Cl)(OC(Cl)(Cl)Cl)=O.C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OCC(O)COC(CCCCCCCCCCCCCCCCC)=O.CCCCCC.C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OCC(COC(CCCCCCCCCCCCCCCCC)=O)O>>C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OCC(COC(CCCCCCCCCCCCCCCCC)=O)OC(=O)Cl | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][C:25](=[O:26])[C@@H:27]([NH:28][C:29](=[O:30])[O:31][CH2:32][c:33]1[cH:34][cH:35][cH:36][cH:37][cH:38]1)[CH:39]([CH3:40])[CH3:41])[OH:42].ClC... | CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl | CCCCCCCCCCCCCCCCCC(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)OC(=O)Cl | null | null | ClCCl | Acylation | OtherReaction | 60794a39c0440c00ffe5af45ae1081850b5b3af5d64dc511aaf170d549f5caf2 | 9d38fe5aab6982b32703d33609e218d4ba6d7a679c958162c14445bc8a2a5539 | c1ccccc1 | Cl-C(-Cl)(-Cl)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C(-Cl)(-Cl)-[Cl;H0;D1;+0:3].[C:4]-[C:5](-[C:6])-[OH;D1;+0:7]>>[C:4]-[C:5](-[C:6])-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](-[Cl;H0;D1;+0:3])=[O;D1;H0:2] | 89 | [{"value": 89.0, "product": "C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)OCC(COC(CCCCCCCCCCCCCCCCC)=O)OC(=O)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Bis(trichloromethyl) carbonate (160 mg; 0.54 mmol) was added with stirring to a solution of 1-(N-benzyloxycarbonyl-L-valyl)-3-stearoylglycerol; 1-(N-benzyloxycarbonyl-L-valyloxy)-3-stearoyloxy-2-propanol; preparative example 4; (660 mg; 1.12 mmol) and triethylamine (200 mg; 2.0 mmol) in dichloromethane (5 ml) at room t... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Trichloro group.Carbonic Ester.Secondary alcohol | Acyl halide.Ether | null | null | c1ccccc1 | HCl | ClCCl | null | 1 | CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>ClCCl>CCCCCCCCCCCCCCCCCC(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)OC(=O)Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b0b04d3442064b36aaa283cbab828c72 | CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F)COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C>>CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F)COC(=O)[C@@H](N)C(C)C | F[C@H]1C[C@@H](O[C@@H]1COC(=O)OCC(COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)OC(CCCCCCCCCCCCCCCCC)=O)N1C=NC=2C(=O)NC(N)=NC12>>F[C@H]1C[C@@H](O[C@@H]1COC(=O)OCC(COC([C@@H](N)C(C)C)=O)OC(CCCCCCCCCCCCCCCCC)=O)N1C=NC=2C(=O)NC(N)=NC12 | O=C(OCc1ccccc1)[NH:50][C@H:49]([C:47]([O:46][CH2:45][CH:21]([O:20][C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19])[CH2:22][O:23][C:24](=[O:25])[O:26][CH2:27][C@H:28]1[O:29][C@@H:30]([n:31]2[cH:32][n:33][c:34]3[c:35](=[O:36])[... | CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F)COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C | CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F)COC(=O)[C@@H](N)C(C)C | null | [Pd] | C(C)(=O)O.CO.C(C)(=O)OCC | Reduction | Hydrogenolysis of amides/imides/carbamates | 087b6600ba91d3df931fe6979f2445c192cbfd59e04fd2d8a10f7c7573ac669f | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | O=c1[nH]cnc2c1ncn2[C@H]1CCCO1 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[C:2](-[C:3])-[NH2;D1;+0:1] | null | [] | null | null | 2 | HOUR | 2′,3′-dideoxy-3′-fluoro-5′-O-[1-(N-CBz-L-valyloxy)-2-stearoyloxy-3-propyloxy carbonyl] guanosine (190 mg), was dissolved in a mixed solvent of methanol (6 ml), ethyl acetate (2 ml) and acetic acid (1 ml). To the solution was added palladium black (30 mg), and the reaction mixture was kept under hydrogen for 2 h. It was... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1 | null | C1CCOC1.c1ncc2nc[nH]c2n1 | HO- | [Pd].C(C)(=O)O.CO.C(C)(=O)OCC | null | 2 | CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F)COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C>[Pd].C(C)(=O)O.CO.C(C)(=O)OCC>CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F)COC(=O)[C@@H](N)C(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1052c84ca7e04af6a968b0aeb97f381d | CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)O.Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](CO)O2)c(=O)[nH]1>>CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F | C1CCC(CC1)N=C=NC2CCCCC2.F[C@H]1C[C@@H](O[C@@H]1CO)N1C=NC=2C(=O)NC(N)=NC12.C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCC(C(=O)O)OC(CCCCCCCCCCCCCCCCC)=O.C=1C=CC2=C(C1)N=NN2O>>F[C@H]1C[C@@H](O[C@@H]1COC(C(COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)OC(CCCCCCCCCCCCCCCCC)=O)=O)N1C=NC=2C(=O)NC(N)=NC12 | O[C:41]([CH:21]([O:20][C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19])[CH2:22][O:23][C:24](=[O:25])[C@@H:26]([NH:27][C:28](=[O:29])[O:30][CH2:31][c:32]1[cH:33][cH:34][cH:35][cH:36][cH:37]1)[CH:38]([CH3:39])[CH3:40])=[O:42].[O... | CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)O.Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](CO)O2)c(=O)[nH]1 | CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F | null | CN(C)C=1C=CN=CC1 | CN(C)C=O | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | O=C(CCOC(=O)CNC(=O)OCc1ccccc1)OC[C@@H]1CC[C@H](n2cnc3c(=O)[nH]cnc32)O1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#8:5]-[C:6]=[O;D1;H0:7].[#8:8]-[C:9]-[C:10]-[OH;D1;+0:11]>>[#8:8]-[C:9]-[C:10]-[O;H0;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#8:5]-[C:6]=[O;D1;H0:7] | null | [] | null | null | 8 | HOUR | A mixture of 2′,3′-dideoxy-3′-fluoroguanosine (404 mg, 1.5 mmole), 3-(N-CBZ-L-valyloxy)-2-stearoyloxy-propanoic acid (1.06 g, 1.75 mmole), DMAP (24 mg, 0.2 mmole) and HOBT (264 mg, 1.82 mmole) was coevaporated two times with DMF and reduced to about 30 ml. DCC (372 mg, 1.8 mmole) was added and the mixture was stirred o... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1.C1CCOC1.c1ncc2nc[nH]c2n1 | HO- | CN(C)C=1C=CN=CC1.CN(C)C=O | null | 8 | CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)O.Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](CO)O2)c(=O)[nH]1>CN(C)C=1C=CN=CC1.CN(C)C=O>CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-75721d22460a45988475492fbbe41595 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(=O)O.Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](CO)O2)c(=O)[nH]1>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F | C1CCC(CC1)N=C=NC2CCCCC2.F[C@H]1C[C@@H](O[C@@H]1CO)N1C=NC=2C(=O)NC(N)=NC12.C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCC(CC(=O)O)COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O.C=1C=CC2=C(C1)N=NN2O>>F[C@H]1C[C@@H](O[C@@H]1COC(CC(COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)=O)N1C=NC=2C(=O)NC(N)=N... | O[C:41]([CH2:40][CH:20]([CH2:19][O:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)=[O:17])[CH2:21][O:22][C:23](=[O:24])[C@@H:25]([NH:26][C:27](=[O:28])[O:29][CH2:30][c:31]1[cH:32][cH:33][cH:34][cH:35][cH:36]1)[CH:37]([CH3:38])[CH3:39])=[O:42].[OH:43][... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(=O)O.Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](CO)O2)c(=O)[nH]1 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F | null | CN(C)C=1C=CN=CC1 | COCCOC | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | O=C(CNC(=O)OCc1ccccc1)OCC(COC(=O)CNC(=O)OCc1ccccc1)CC(=O)OC[C@@H]1CC[C@H](n2cnc3c(=O)[nH]cnc32)O1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#8:5]-[C:6]-[C:7]-[OH;D1;+0:8]>>[#8:5]-[C:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | null | [] | null | null | 8 | HOUR | A solution of 2′,3′-dideoxy-3′-fluoroguanosine (1.35 g, 5 mmole), 3,3-bis (N-CBZ-L-valyloxymethyl)-propionic acid (3.6 g, 6 mmole), DMAP (0.061 g, 0.5 mmole) and HOBT (0.81 g, 6 mmole) was coevaporated two times with DME and reduced to about 120 ml. DCC (1.24 g, 6 mmole) was added and the mixture was stirred overnight ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1.c1ccccc1.C1CCOC1.c1ncc2nc[nH]c2n1 | HO- | CN(C)C=1C=CN=CC1.COCCOC | null | 8 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(=O)O.Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](CO)O2)c(=O)[nH]1>CN(C)C=1C=CN=CC1.COCCOC>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3290d089eb1f4d0595ac41189cffa79b | CCCCCCCCCCCCCCCCCC(=O)OCC(CCOC(=O)Cl)COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C.Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](CO)O2)c(=O)[nH]1>>CCCCCCCCCCCCCCCCCC(=O)OCC(CCOC(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F)COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C | C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCC(CCOC(=O)Cl)COC(CCCCCCCCCCCCCCCCC)=O.F[C@H]1C[C@@H](O[C@@H]1CO)N1C=NC=2C(=O)NC(N)=NC12.N1=CC=CC=C1>>F[C@H]1C[C@@H](O[C@@H]1COC(=O)OCCC(COC(CCCCCCCCCCCCCCCCC)=O)COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)N1C=NC=2C(=O)NC(N)=NC12 | Cl[C:26]([O:25][CH2:24][CH2:23][CH:22]([CH2:21][O:20][C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19])[CH2:47][O:48][C:49](=[O:50])[C@@H:51]([NH:52][C:53](=[O:54])[O:55][CH2:56][c:57]1[cH:58][cH:59][cH:60][cH:61][cH:62]1)[CH:6... | CCCCCCCCCCCCCCCCCC(=O)OCC(CCOC(=O)Cl)COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C.Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](CO)O2)c(=O)[nH]1 | CCCCCCCCCCCCCCCCCC(=O)OCC(CCOC(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F)COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C | null | null | ClCCl.CN(C)C=O | Acylation | Schotten-Baumann to ester | ab2604cac7a0887c37303ad0fec59fb6a84cf40820c840730a9f7f5636dcc83e | 7ed0ec8c4c25c8af523f531911c9dd0a60119de4cab841f882ce9a65c39be54c | O=C(CNC(=O)OCc1ccccc1)OCCCCOC(=O)OC[C@@H]1CC[C@H](n2cnc3c(=O)[nH]cnc32)O1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[#8:5]-[C:6]-[C:7]-[OH;D1;+0:8]>>[#8:5]-[C:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4] | null | [] | null | null | 3 | DAY | To a solution of 2′,3′-dideoxy-3′-fluoroguanosine (269 mg, 1.0 mmole in absolute DMF were added pyridine (198 mg, 2.5 mmole) and a solution of 3-(N-CBZ-L-valyloxymethyl)-4-stearoyloxy-butoxycarbonyl chloride (750 mg, 1.1 mmole) in 5 ml dichloromethane. The mixture was stirred for three days at room temperature. The sol... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary alcohol | Carbonic Ester | null | null | C1CCOC1.c1ncc2nc[nH]c2n1.c1ccccc1 | HCl | ClCCl.CN(C)C=O | null | 72 | CCCCCCCCCCCCCCCCCC(=O)OCC(CCOC(=O)Cl)COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C.Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](CO)O2)c(=O)[nH]1>ClCCl.CN(C)C=O>CCCCCCCCCCCCCCCCCC(=O)OCC(CCOC(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F)COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7eaf5d761c6343b78b4c37dfaf2a2b7a | BrCc1ccccc1.CCCCCCCCCCCCCCCCC(O)C(=O)O>>CCCCCCCCCCCCCCCCC(O)C(=O)OCc1ccccc1 | C(C1=CC=CC=C1)Br.OC(C(=O)O)CCCCCCCCCCCCCCCC.CC(C)([O-])C.[K+]>>OC(C(=O)OCC1=CC=CC=C1)CCCCCCCCCCCCCCCC | Br[CH2:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]([OH:18])[C:19](=[O:20])[OH:21]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2... | BrCc1ccccc1.CCCCCCCCCCCCCCCCC(O)C(=O)O | CCCCCCCCCCCCCCCCC(O)C(=O)OCc1ccccc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]>>[C:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 60 | CELSIUS | 1 | HOUR | To a stirred solution of DL-2-hydroxystearic acid (3.0 g, 10 mmole) in 20 ml dry DMF was added potassium tert-butoxide (1.23 g, 11 mmole) and the mixture was stirred for one hour at 60° C. Benzyl bromide (2.14 g, 12.5 mmole) was added and the mixture was stirred for six hours at 80° C. The mixture was evaporated under ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | c1ccccc1 | HBr | CN(C)C=O | 60 | 1 | BrCc1ccccc1.CCCCCCCCCCCCCCCCC(O)C(=O)O>CN(C)C=O>CCCCCCCCCCCCCCCCC(O)C(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6eaf4898584d40e39f4dd582529ada70 | CC(C)[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O.CCCCCCCCCCCCCCCCC(O)C(=O)OCc1ccccc1>>CCCCCCCCCCCCCCCCC(OC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C)C(=O)OCc1ccccc1 | C(C1=CC=CC=C1)OC(C(CCCCCCCCCCCCCCCC)O)=O.C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N[C@@H](C(C)C)C(=O)O.C1CCC(CC1)N=C=NC2CCCCC2>>C(C1=CC=CC=C1)OC(C(CCCCCCCCCCCCCCCC)OC([C@@H](NC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C12)C(C)C)=O)=O | O[C:19](=[O:20])[C@@H:21]([NH:22][C:23](=[O:24])[O:25][CH2:26][CH:27]1[c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]2-[c:34]2[cH:35][cH:36][cH:37][cH:38][c:39]21)[CH:40]([CH3:41])[CH3:42].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]([OH:18])[C... | CC(C)[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O.CCCCCCCCCCCCCCCCC(O)C(=O)OCc1ccccc1 | CCCCCCCCCCCCCCCCC(OC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C)C(=O)OCc1ccccc1 | null | CN(C)C=1C=CN=CC1 | ClCCl | Acylation | Esterification of Carboxylic Acids | e916c5b009194e30c618975b40d7a233bfcf81339e65494c4e365f67cc5e011d | 12ba7405a548c6b1674f05065819c74f53f1b6165cd54e84e1f2f208042fe660 | O=C(CNC(=O)OCC1c2ccccc2-c2ccccc21)OCC(=O)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[C:9](-[OH;D1;+0:10])-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14]>>[C:8]-[C:9](-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7])-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14] | null | [] | null | null | 8 | HOUR | To a solution of benzyl-2-hydroxystearate (3.2 g, 8.2 mmole), N-FMOC-L-valine (3.4 g, 10 mmole) and DMAP (0.12 g, 1 mmole) in 80 ml dichloromethane was added a solution of DCC (2.5 g, 12 mmole) and the mixture was stirred overnight at room temperature. The mixture was cooled to 5° C. and the urethane was filtered. The ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary alcohol | Ester | null | null | c1ccccc1.c1ccc2c(c1)Cc1ccccc12 | HO- | CN(C)C=1C=CN=CC1.ClCCl | null | 8 | CC(C)[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O.CCCCCCCCCCCCCCCCC(O)C(=O)OCc1ccccc1>CN(C)C=1C=CN=CC1.ClCCl>CCCCCCCCCCCCCCCCC(OC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C)C(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cc33e408facb4864b1e874bd1cc7272e | CCCCCCCCCCCCCCCCC(OC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C)C(=O)OCc1ccccc1>>CCCCCCCCCCCCCCCCC(OC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C)C(=O)O | C(C1=CC=CC=C1)OC(C(CCCCCCCCCCCCCCCC)OC([C@@H](NC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C12)C(C)C)=O)=O>>C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N[C@@H](C(C)C)C(=O)OC(C(=O)O)CCCCCCCCCCCCCCCC | c1ccc(C[O:45][C:43]([CH:17]([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[O:18][C:19](=[O:20])[C@@H:21]([NH:22][C:23](=[O:24])[O:25][CH2:26][CH:27]2[c:28]3[cH:29][cH:30][cH:31][cH:32][c:33]3-[c:34]3[cH:35][cH:36][cH:37][cH:38][c:39]32)[CH:40]([C... | CCCCCCCCCCCCCCCCC(OC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C)C(=O)OCc1ccccc1 | CCCCCCCCCCCCCCCCC(OC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C)C(=O)O | null | [Pd] | C(C)(=O)OCC | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2c(c1)Cc1ccccc1-2 | [C:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1>>[C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4] | null | [] | null | null | null | null | A solution of benzyl-2-(N-FMOC-L-valyloxy)stearate (4.4 g, 6.2 mmole) in 50 ml ethyl acetate was hydrogenated with 10% palladium on charcoal (0.5 g) with normal pressure for two hours. The catalyst was filtered and washed with ethyl acetate and 1,4-dioxane. The solution was evaporated under reduced pressure and the pro... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | c1ccc2c(c1)Cc1ccccc12 | Other | [Pd].C(C)(=O)OCC | null | null | CCCCCCCCCCCCCCCCC(OC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C)C(=O)OCc1ccccc1>[Pd].C(C)(=O)OCC>CCCCCCCCCCCCCCCCC(OC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5c010298e2b44b96af3f510dd0f0351d | CCCCCCCCCCCCCCCCC(OC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C)C(=O)O.Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](CO)O2)c(=O)[nH]1>>CCCCCCCCCCCCCCCCC(OC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C)C(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F | C1CCC(CC1)N=C=NC2CCCCC2.F[C@H]1C[C@@H](O[C@@H]1CO)N1C=NC=2C(=O)NC(N)=NC12.C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N[C@@H](C(C)C)C(=O)OC(C(=O)O)CCCCCCCCCCCCCCCC.C=1C=CC2=C(C1)N=NN2O>>F[C@H]1C[C@@H](O[C@@H]1COC(C(CCCCCCCCCCCCCCCC)OC([C@@H](NC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C12)C(C)C)=O)=O)N1C=NC=2C(=O)NC(N)=NC12 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]([O:18][C:19](=[O:20])[C@@H:21]([NH:22][C:23](=[O:24])[O:25][CH2:26][CH:27]1[c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]2-[c:34]2[cH:35][cH:36][cH:37][cH:38][c:39]21)[CH:40]([CH3:41])[CH3:42])[C:43... | CCCCCCCCCCCCCCCCC(OC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C)C(=O)O.Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](CO)O2)c(=O)[nH]1 | CCCCCCCCCCCCCCCCC(OC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C)C(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F | null | CN(C)C=1C=CN=CC1 | CN(C)C=O | Heteroatom Alkylation and Arylation | Esterification of Carboxylic Acids | 3f9a9ace480b666da05fcfe5450d12b5c1ea5b0d435c195e1dd4bd20281604bb | dcbf04ec563ed0e9dfc79070490a028958024079a671c385858bb18cc8ec995a | O=C(CNC(=O)OCC1c2ccccc2-c2ccccc21)OCC(=O)OC[C@@H]1CC[C@H](n2cnc3c(=O)[nH]cnc32)O1 | O-[CH2;D2;+0:1]-[C:2](-[C:3])-[#8:4]-[C:5].[C:6]-[C:7](=[O;D1;H0:8])-[OH;D1;+0:9]>>[C:6]-[C:7](=[O;D1;H0:8])-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2](-[C:3])-[#8:4]-[C:5] | null | [] | null | null | 8 | HOUR | A mixture of 2′,3′-dideoxy-3′-fluoroguanosine (404 mg, 1.5 mmole), 2-(N-FMOC-L-valyloxy)stearic acid (1.24 g, 2 mmole), DMAP (24 mg, 0.2 mmole) and HOBT (264 mg, 1,95 mmole) was coevaporated two times with DMF and reduced to about 30 ml. DCC (372 mg, 1.8 mmole) was added and the mixture was stirred overnight at room te... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | C1CCOC1.c1ncc2nc[nH]c2n1.c1ccc2c(c1)Cc1ccccc12 | HO- | CN(C)C=1C=CN=CC1.CN(C)C=O | null | 8 | CCCCCCCCCCCCCCCCC(OC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C)C(=O)O.Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](CO)O2)c(=O)[nH]1>CN(C)C=1C=CN=CC1.CN(C)C=O>CCCCCCCCCCCCCCCCC(OC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C)C(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-19617dbe39d74ba7af385e1285825260 | CCCCCCCCCCCCCCCCC(OC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C)C(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F>>CCCCCCCCCCCCCCCCC(OC(=O)[C@@H](N)C(C)C)C(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F | C(C)(=O)O.F[C@H]1C[C@@H](O[C@@H]1COC(C(CCCCCCCCCCCCCCCC)OC([C@@H](NC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C12)C(C)C)=O)=O)N1C=NC=2C(=O)NC(N)=NC12.C1CCC2=NCCCN2CC1>>F[C@H]1C[C@@H](O[C@@H]1COC(C(CCCCCCCCCCCCCCCC)OC([C@@H](N)C(C)C)=O)=O)N1C=NC=2C(=O)NC(N)=NC12 | O=C(OCC1c2ccccc2-c2ccccc21)[NH:22][C@H:21]([C:19]([O:18][CH:17]([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[C:26](=[O:27])[O:28][CH2:29][C@H:30]1[O:31][C@@H:32]([n:33]2[cH:34][n:35][c:36]3[c:37](=[O:38])[nH:39][c:40]([NH2:41])[n:42][c:43]23)[C... | CCCCCCCCCCCCCCCCC(OC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C)C(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F | CCCCCCCCCCCCCCCCC(OC(=O)[C@@H](N)C(C)C)C(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F | null | null | CN(C)C=O | Reduction | Hydrogenolysis of amides/imides/carbamates | 6b8c76d50ec667b483b13f7e325104eed6ba06fddb821da46e405c5dce0a3de5 | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | O=c1[nH]cnc2c1ncn2[C@H]1CCCO1 | O=C(-O-C-C1-c2:c:c:c:c:c:2-c2:c:c:c:c:c:2-1)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7]-[C:8](-[#8:9])=[O;D1;H0:10]>>[#8:9]-[C:8](=[O;D1;H0:10])-[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[C:2](-[C:3])-[NH2;D1;+0:1] | null | [] | null | null | 5 | MINUTE | To a solution of 2′,3′-dideoxy-3′-fluoro-5′-O-[2-(N-FMOC-L-valyloxy) stearoyl] guanosine (800 mg, 0.89 mmole) in 15 ml DMF was added DBU (1.35 g, 8.9 mmole) and the mixture was stirred for 5 minutes at room temperature. Acetic acid (2 ml) was added and the mixture was evaporated under reduced pressure. Water (20 ml) we... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccc2c(c1)Cc1ccccc12 | null | C1CCOC1.c1ncc2nc[nH]c2n1 | HO- | CN(C)C=O | null | 0.083333 | CCCCCCCCCCCCCCCCC(OC(=O)[C@@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C)C(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F>CN(C)C=O>CCCCCCCCCCCCCCCCC(OC(=O)[C@@H](N)C(C)C)C(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ee3cee96d5f64d1fada78751a9e03d51 | Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](COC(=O)CCC(=O)OC(COCc3ccccc3)COCc3ccccc3)O2)c(=O)[nH]1>>Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](COC(=O)CCC(=O)OC(CO)CO)O2)c(=O)[nH]1 | F[C@H]1C[C@@H](O[C@@H]1COC(CCC(=O)OC(COCC1=CC=CC=C1)COCC1=CC=CC=C1)=O)N1C=NC=2C(=O)NC(N)=NC12>>F[C@H]1C[C@@H](O[C@@H]1COC(CCC(=O)OC(CO)CO)=O)N1C=NC=2C(=O)NC(N)=NC12 | c1ccc(C[O:25][CH2:24][CH:23]([O:22][C:20]([CH2:19][CH2:18][C:16]([O:15][CH2:14][C@@H:13]2[C@@H:11]([F:12])[CH2:10][C@H:9]([n:8]3[c:4]4[n:3][c:2]([NH2:1])[nH:31][c:29](=[O:30])[c:5]4[n:6][cH:7]3)[O:28]2)=[O:17])=[O:21])[CH2:26][O:27]Cc2ccccc2)cc1>>[NH2:1][c:2]1[n:3][c:4]2[c:5]([n:6][cH:7][n:8]2[C@H:9]2[CH2:10][C@H:11]([... | Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](COC(=O)CCC(=O)OC(COCc3ccccc3)COCc3ccccc3)O2)c(=O)[nH]1 | Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](COC(=O)CCC(=O)OC(CO)CO)O2)c(=O)[nH]1 | null | [Pd] | C(C)(=O)O.CO.C(C)(=O)OCC | Deprotection | OtherReaction | 100cee52e7ebab61be4feb01c3586ebae368005fa572c209e799eba752880fb0 | 2f23bf710218006c93ff728dc99485ec1b0a0e5cb41fb3252e62eb1ed984c4ac | O=c1[nH]cnc2c1ncn2[C@H]1CCCO1 | C(-[O;H0;D2;+0:1]-[C:2]-[C:3]-[C:4]-[O;H0;D2;+0:5]-C-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[OH;D1;+0:1]-[C:2]-[C:3]-[C:4]-[OH;D1;+0:5] | null | [] | null | null | null | null | A solution of 2′,3′-dideoxy-3′-fluoro-5′-O-[3-(1,3-dibenzyloxy-2-propyloxy carbonyl)propanoyl]guanosine (3.2 g, 5.13 mmole) in 50 ml ethyl acetate, 50 ml methanol and 10 ml acetic acid was hydrogenated with palladium black (0.6 g) under 40 psi overnight. The catalyst was filtered and washed with methanol, The solution ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Primary alcohol.Primary alcohol | c1ccccc1.c1ccccc1 | null | c1ncc2[nH]cnc2n1.C1CCOC1 | Other | [Pd].C(C)(=O)O.CO.C(C)(=O)OCC | null | null | Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](COC(=O)CCC(=O)OC(COCc3ccccc3)COCc3ccccc3)O2)c(=O)[nH]1>[Pd].C(C)(=O)O.CO.C(C)(=O)OCC>Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](COC(=O)CCC(=O)OC(CO)CO)O2)c(=O)[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b4cb5d2d8b4a4419bf72dc1b67751abb | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](COC(=O)CCC(=O)OC(CO)CO)O2)c(=O)[nH]1>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(CO)OC(=O)CCC(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F | C1CCC(CC1)N=C=NC2CCCCC2.F[C@H]1C[C@@H](O[C@@H]1COC(CCC(=O)OC(CO)CO)=O)N1C=NC=2C(=O)NC(N)=NC12.C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)O.C=1C=CC2=C(C1)N=NN2O>>F[C@H]1C[C@@H](O[C@@H]1COC(CCC(=O)OC(COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)CO)=O)N1C=NC=2C(=O)NC(N)=NC12 | [CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[OH:18].O[CH2:19][CH:20]([CH2:21][OH:22])[O:23][C:24](=[O:25])[CH2:26][CH2:27][C:28](=[O:29])[O:30][CH2:31][C@H:32]1[O:33][C@@H:34]([n:35]2[cH:36][n:37][c:38]3[c:39](=[O:40])[nH:41][c:42]([NH2:43])[n:... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](COC(=O)CCC(=O)OC(CO)CO)O2)c(=O)[nH]1 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(CO)OC(=O)CCC(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F | null | CN(C)C=1C=CN=CC1 | CN(C)C=O | Heteroatom Alkylation and Arylation | Esterification of Carboxylic Acids | 3f9a9ace480b666da05fcfe5450d12b5c1ea5b0d435c195e1dd4bd20281604bb | dcbf04ec563ed0e9dfc79070490a028958024079a671c385858bb18cc8ec995a | O=C(CCC(=O)OC[C@@H]1CC[C@H](n2cnc3c(=O)[nH]cnc32)O1)OCCOC(=O)CNC(=O)OCc1ccccc1 | O-[CH2;D2;+0:1]-[C:2](-[C:3])-[#8:4]-[C:5]=[O;D1;H0:6].[C:7]-[C:8](=[O;D1;H0:9])-[OH;D1;+0:10]>>[C:3]-[C:2](-[#8:4]-[C:5]=[O;D1;H0:6])-[CH2;D2;+0:1]-[O;H0;D2;+0:10]-[C:8](-[C:7])=[O;D1;H0:9] | null | [] | null | null | 72 | HOUR | A mixture of 2′,3′-dideoxy-3′-fluoro-5′-O-[3-(1,3-dihydroxy-2-propyloxy carbonyl)-propanoyl] guanosine (1.3 g, 2.93 mmole), N-CBZ-L-valine (1.00 g, 4 mmole), HOBT (0.54 g, 4 mmole) and DMAP (48.8 mg, 0.4 mmole) was coevaporated two times with DMF and reduced to about 60 ml. DCC (0.91 g, 4.4 mmole) was added and the mix... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1.C1CCOC1.c1ncc2nc[nH]c2n1 | HO- | CN(C)C=1C=CN=CC1.CN(C)C=O | null | 72 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](COC(=O)CCC(=O)OC(CO)CO)O2)c(=O)[nH]1>CN(C)C=1C=CN=CC1.CN(C)C=O>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(CO)OC(=O)CCC(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f876926012434deaac62fded3adf3f65 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](CO)O2)c(=O)[nH]1>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)C(O)[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F | F[C@H]1C[C@@H](O[C@@H]1CO)N1C=NC=2C(=O)NC(N)=NC12.C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)O.ON1N=NC2=C1C=CC=C2.C1CCC(CC1)N=C=NC2CCCCC2>>C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)C([C@@H]1[C@H](C[C@@H](O1)N1C=NC=2C(=O)NC(N)=NC12)F)O | O[C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)=[O:17].[CH2:18]([OH:19])[C@H:20]1[O:21][C@@H:22]([n:23]2[cH:24][n:25][c:26]3[c:27](=[O:28])[nH:29][c:30]([NH2:31])[n:32][c:33]23)[CH2:34][C@@H:35]1[F:36]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](CO)O2)c(=O)[nH]1 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)C(O)[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F | null | CN(C1=CC=NC=C1)C | CN(C)C=O | C-C Coupling | OtherReaction | 2c2a3c3f27eaa3b95e57dbf9c7251ce7b9a5fa8339e5b0a99b92c287a42ddc63 | 5bef6096b9bde5994ecc7867e116432a7be29312b8075fec1652e285111e590f | O=C(CNC(=O)OCc1ccccc1)C[C@@H]1CC[C@H](n2cnc3c(=O)[nH]cnc32)O1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[#8:9]-[C:10](-[CH2;D2;+0:11]-[O;D1;H1:12])-[C:13]>>[C:8]-[#8:9]-[C:10](-[CH;D3;+0:11](-[O;D1;H1:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7])-[C:13] | null | [] | null | null | 72 | HOUR | To a solution of 2′,3′—dideoxy-3′—fluoroguanosine (810 mg, 3 mmole) and 4-dimethylaminopyridine (73 mg, 0.6 mmole), N-CBz-L-valine (1.5 g, 6 mmole) and 1-hydroxybenzotriazole (810 mg, 6 mmole) in DMF (20 ml) was added DCC (1.36 g, 6.6 mmole). After 72 h, the reaction mixture was filtered and concentrated in vacuo. 5′-(... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ketone | null | null | c1ccccc1.C1CCOC1.c1ncc2nc[nH]c2n1 | HO- | CN(C1=CC=NC=C1)C.CN(C)C=O | null | 72 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](CO)O2)c(=O)[nH]1>CN(C1=CC=NC=C1)C.CN(C)C=O>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)C(O)[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4ed5a749f2e24b50968453fa79f52fe3 | COc1ccc(CC(C)(OC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)C(=O)[O-])cc1>>CC(OC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)O | COC1=CC=C(CC(C(=O)[O-])(C)OC([C@@H](NC(=O)OCC2=CC=CC=C2)C(C)C)=O)C=C1.FC(C(=O)O)(F)F>>C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OC(C(=O)O)C | COc1ccc(C[C:2]([CH3:1])([O:3][C:4](=[O:5])[C@@H:6]([NH:7][C:8](=[O:9])[O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH:18]([CH3:19])[CH3:20])[C:21](=[O:22])[O-:23])cc1>>[CH3:1][CH:2]([O:3][C:4](=[O:5])[C@@H:6]([NH:7][C:8](=[O:9])[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[CH:18]([CH3:19])[CH... | COc1ccc(CC(C)(OC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)C(=O)[O-])cc1 | CC(OC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)O | null | null | ClCCl | Reduction | OtherReaction | 26c35b0d17883800cad69ca198f384a36d8945673d343444de8614ec29aef208 | f4d3254a6b2ee64471c86a7ba74096ca0ae30d9c0dffa5d9df7f7259f5176c6f | c1ccccc1 | C-O-c1:c:c:c(-C-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[#8:3]-[C:4](-[C:5])=[O;D1;H0:6])-[C:7](-[O-;H0;D1:8])=[O;D1;H0:9]):c:c:1>>[C:5]-[C:4](=[O;D1;H0:6])-[#8:3]-[CH;D3;+0:1](-[C;D1;H3:2])-[C:7](=[O;D1;H0:9])-[OH;D1;+0:8] | null | [] | null | null | 1 | HOUR | To a solution of 4-methoxybenzyl-2-(N-CBZ-L-valyloxy)-propionate (7.8 g, 17.5 mmole) in dichloromethane (100 ml) was added trifluoroacetic acid (10 ml) and the solution was stirred for one hour at room temperature. The solution was evaporated under reduced pressure and the product was isolated by silica gel column chro... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Carboxylic acid.Ester | c1ccccc1 | null | c1ccccc1 | HO- | ClCCl | null | 1 | COc1ccc(CC(C)(OC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)C(=O)[O-])cc1>ClCCl>CC(OC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-08558c34e92d4866957fabdb7ccf080c | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)OC(=O)CCC(=O)O.Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](CO)O2)c(=O)[nH]1>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)OC(=O)CCC(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F | C1CCC(CC1)N=C=NC2CCCCC2.F[C@H]1C[C@@H](O[C@@H]1CO)N1C=NC=2C(=O)NC(N)=NC12.C=1C=CC2=C(C1)N=NN2O.C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCC(COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)OC(CCC(=O)O)=O>>F[C@H]1C[C@@H](O[C@@H]1COC(CCC(=O)OC(COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)=O)N1C=NC... | O[C:45]([CH2:44][CH2:43][C:41]([O:40][CH:20]([CH2:19][O:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)=[O:17])[CH2:21][O:22][C:23](=[O:24])[C@@H:25]([NH:26][C:27](=[O:28])[O:29][CH2:30][c:31]1[cH:32][cH:33][cH:34][cH:35][cH:36]1)[CH:37]([CH3:38])[CH3... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)OC(=O)CCC(=O)O.Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](CO)O2)c(=O)[nH]1 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)OC(=O)CCC(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F | null | CN(C)C=1C=CN=CC1 | CN(C)C=O | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | O=C(CCC(=O)OC(COC(=O)CNC(=O)OCc1ccccc1)COC(=O)CNC(=O)OCc1ccccc1)OC[C@@H]1CC[C@H](n2cnc3c(=O)[nH]cnc32)O1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7].[#8:8]-[C:9]-[C:10]-[OH;D1;+0:11]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:11]-[C:10]-[C:9]-[#8:8] | null | [] | null | null | 8 | HOUR | A mixture of 2′,3′-dideoxy-3′-fluoroguanosine (17.8 g, 66 mmole), HOBT (10.64 g, 78.8 mmole), succinic acid 1,3-bis-(N-CBZ-L-valyloxy)-2-propyl ester (52 g, 78.8 mmole) and DMAP (0.96 g, 7.88 mmole) was coevaporated two times with DMF and redued to about 500 ml. DCC (17.3 g, 84 mmole) was added and the mixture was stir... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1.c1ccccc1.C1CCOC1.c1ncc2nc[nH]c2n1 | HO- | CN(C)C=1C=CN=CC1.CN(C)C=O | null | 8 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)OC(=O)CCC(=O)O.Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](CO)O2)c(=O)[nH]1>CN(C)C=1C=CN=CC1.CN(C)C=O>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)OC(=O)CCC(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-eb3243471659495394ef205fb598930a | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(OC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)O.Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](CO)O2)c(=O)[nH]1>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(OC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F | C1CCC(CC1)N=C=NC2CCCCC2.F[C@H]1C[C@@H](O[C@@H]1CO)N1C=NC=2C(=O)NC(N)=NC12.C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OC(C(=O)O)COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O.C=1C=CC2=C(C1)N=NN2O>>F[C@H]1C[C@@H](O[C@@H]1COC(C(COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)OC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)=O)N1C=NC=2C(=O)NC(N)=NC12 | O[C:39]([CH:20]([CH2:19][O:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)=[O:17])[O:21][C:22](=[O:23])[C@@H:24]([NH:25][C:26](=[O:27])[O:28][CH2:29][c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1)[CH:36]([CH3:37])[CH3:38])=[O:40].[OH:41][CH2:42][C@H:43]1... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(OC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)O.Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](CO)O2)c(=O)[nH]1 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(OC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F | null | CN(C)C=1C=CN=CC1 | CN(C)C=O | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | O=C(CNC(=O)OCc1ccccc1)OCC(OC(=O)CNC(=O)OCc1ccccc1)C(=O)OC[C@@H]1CC[C@H](n2cnc3c(=O)[nH]cnc32)O1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#8:5]-[C:6]=[O;D1;H0:7].[#8:8]-[C:9]-[C:10]-[OH;D1;+0:11]>>[#8:8]-[C:9]-[C:10]-[O;H0;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#8:5]-[C:6]=[O;D1;H0:7] | null | [] | null | null | 2 | DAY | A mixture of 2′,3′-dideoxy-3′-fluoroguanosine (2.15 g, 8 mmole), 2,3-bis-(N-CBZ-L-valyloxy)-propanoic acid (6.2 g, 10.8 mmole), DMAP (244 mg, 2 mmole) and HOBT (1.46 g, 10.8 mmole) was coevaporated two times with DMF and reduced to about 120 ml. DCC (2.48 g, 12 mmole) was added and the mixture was stirred for two days ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1.c1ccccc1.C1CCOC1.c1ncc2nc[nH]c2n1 | HO- | CN(C)C=1C=CN=CC1.CN(C)C=O | null | 48 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(OC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)O.Nc1nc2c(ncn2[C@H]2C[C@H](F)[C@@H](CO)O2)c(=O)[nH]1>CN(C)C=1C=CN=CC1.CN(C)C=O>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(OC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)OC[C@H]1O[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@@H]1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c1a20887e13a4fd4a3b43007748bb6c4 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.OCC(O)CBr>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(O)CBr | BrCC(CO)O.C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)O.C1CCC(CC1)N=C=NC2CCCCC2>>BrCC(COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)O | O[C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)=[O:17].[OH:18][CH2:19][CH:20]([OH:21])[CH2:22][Br:23]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O:18][CH2:19][CH:20]([OH:21])... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.OCC(O)CBr | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(O)CBr | null | CN(C)C=1C=CN=CC1 | ClCCl | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[C:9]-[OH;D1;+0:10]>>[C:8]-[C:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7] | null | [] | null | null | 2 | DAY | To a stirred solution of 3-bromo-1,2-propanediol (10.85 g, 70 mmole), N-CBz-L-valine (10.05 g, 40 mmole) and DMAP (0.49 g, 4 mmol) in 250 ml dichloromethane was added dropwise a solution of DCC (9.1 g, 44 mmol) in 50 ml dichloromethane at about 10° C. The mixture was stirred for two days at room temperature and then co... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | CN(C)C=1C=CN=CC1.ClCCl | null | 48 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.OCC(O)CBr>CN(C)C=1C=CN=CC1.ClCCl>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(O)CBr |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-83d59a1f245e4f8381366cb71fc08f6e | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(O)CBr.CCCCCCCCCCCCCCCCCC(=O)Cl>>CCCCCCCCCCCCCCCCCC(=O)OC(CBr)COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C | C(O)([O-])=O.[Na+].BrCC(COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)O.N1=CC=CC=C1.C(CCCCCCCCCCCCCCCCC)(=O)Cl>>BrCC(COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)OC(CCCCCCCCCCCCCCCCC)=O | [OH:20][CH:21]([CH2:22][Br:23])[CH2:24][O:25][C:26](=[O:27])[C@@H:28]([NH:29][C:30](=[O:31])[O:32][CH2:33][c:34]1[cH:35][cH:36][cH:37][cH:38][cH:39]1)[CH:40]([CH3:41])[CH3:42].Cl[C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19]... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(O)CBr.CCCCCCCCCCCCCCCCCC(=O)Cl | CCCCCCCCCCCCCCCCCC(=O)OC(CBr)COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C | null | null | ClCCl | Acylation | Schotten-Baumann to ester | 27b76e29491fa7db5375755e15223de884a194f57a493147db0b5495ea981908 | d47ab90ace9b5dcd818151c10aae400dcf599f5a3476072b8dfedc474e97c335 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6](-[C:7])-[OH;D1;+0:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:8]-[C:6](-[C:5])-[C:7] | null | [] | null | null | 8 | HOUR | To a stirred solution of 3-bromo-2-hydroxy-1-(N-CBZ-L-valyloxy)-propane (7.9 g, 20 mmol) and pyridin (3.2 g, 40 mmol) in 250 ml dichloromethane was added dropwise a solution of stearoyl chloride (9.1 g, 30 mmol) in 50 ml dichloromethane between 10° C. and 15° C. The solution was stirred overnight at room temperature. 1... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary alcohol | Ester | null | null | c1ccccc1 | HCl | ClCCl | null | 8 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(O)CBr.CCCCCCCCCCCCCCCCCC(=O)Cl>ClCCl>CCCCCCCCCCCCCCCCCC(=O)OC(CBr)COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0de3169b85e14239aa358b86287bb936 | CCCCCCCCCCCCCCCCCC(=O)OCC(CCCC(=O)O)COC(=O)[C@@H](NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(C)C.O=C(O)c1cc(=O)c2c(OCC(O)COc3cccc4oc(C(=O)O)cc(=O)c34)cccc2o1>>CCCCCCCCCCCCCCCCCC(=O)OCC(CCCC(=O)OC(COc1cccc2oc(C(=O)O)cc(=O)c12)COc1cccc2oc(C(=O)O)cc(=O)c12)COC(=O)[C@@H](NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(C)C | C(=O)(O)C=1OC2=CC=CC(=C2C(C1)=O)OCC(COC1=C2C(C=C(OC2=CC=C1)C(=O)O)=O)O.C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCC(CCCC(=O)O)COC(CCCCCCCCCCCCCCCCC)=O.CN(C)C1=NC=CC=C1.C1CCC(CC1)N=C=NC2CCCCC2>>C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCC(CCCC(=O)OC(COC1=C2C(C=C(OC2=CC=C1)C(=O)O)=O)CO... | O[C:26]([CH2:25][CH2:24][CH2:23][CH:22]([CH2:21][O:20][C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19])[CH2:62][O:63][C:64](=[O:65])[C@@H:66]([NH:67][C:68]([c:69]1[cH:70][cH:71][cH:72][cH:73][cH:74]1)([c:75]1[cH:76][cH:77][cH:... | CCCCCCCCCCCCCCCCCC(=O)OCC(CCCC(=O)O)COC(=O)[C@@H](NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(C)C.O=C(O)c1cc(=O)c2c(OCC(O)COc3cccc4oc(C(=O)O)cc(=O)c34)cccc2o1 | CCCCCCCCCCCCCCCCCC(=O)OCC(CCCC(=O)OC(COc1cccc2oc(C(=O)O)cc(=O)c12)COc1cccc2oc(C(=O)O)cc(=O)c12)COC(=O)[C@@H](NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(C)C | null | null | ClCCl | Acylation | Esterification of Carboxylic Acids | e916c5b009194e30c618975b40d7a233bfcf81339e65494c4e365f67cc5e011d | 12ba7405a548c6b1674f05065819c74f53f1b6165cd54e84e1f2f208042fe660 | O=C(CNC(c1ccccc1)(c1ccccc1)c1ccccc1)OCCCCCC(=O)OC(COc1cccc2occc(=O)c12)COc1cccc2occc(=O)c12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6](-[C:7])-[OH;D1;+0:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:8]-[C:6](-[C:5])-[C:7] | null | [] | null | null | 3 | DAY | To a solution of the dibenzyl ester of 1,3-bis-(2-carboxychromon-5-yloxy)propan-2-ol (270 mg, 0.42 mmole), 5-(N-Trityl-L-valyloxymethyl)-6-stearoyloxyhexanoic acid (323 mg, 0.42 mmol) and dimethylaminopyridine (6 mg, 0.05 mmol) in dichloromethane was added DCC (92 mg, 0.45 mmol). After 3 days, the reaction mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary alcohol | Ester | null | null | c1ccc2ccccc2o1.c1ccc2ccccc2o1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | ClCCl | null | 72 | CCCCCCCCCCCCCCCCCC(=O)OCC(CCCC(=O)O)COC(=O)[C@@H](NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(C)C.O=C(O)c1cc(=O)c2c(OCC(O)COc3cccc4oc(C(=O)O)cc(=O)c34)cccc2o1>ClCCl>CCCCCCCCCCCCCCCCCC(=O)OCC(CCCC(=O)OC(COc1cccc2oc(C(=O)O)cc(=O)c12)COc1cccc2oc(C(=O)O)cc(=O)c12)COC(=O)[C@@H](NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-30f813ea36e24d68a7d9102406f4e073 | CCCCCCCCCCCCCCCCCC(=O)OCC(CCCC(=O)OC(COc1cccc2oc(C(=O)O)cc(=O)c12)COc1cccc2oc(C(=O)O)cc(=O)c12)COC(=O)[C@@H](NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(C)C>>CCCCCCCCCCCCCCCCCC(=O)OCC(CCCC(=O)OC(COc1cccc2oc(C(=O)O)cc(=O)c12)COc1cccc2oc(C(=O)O)cc(=O)c12)COC(=O)[C@@H](N)C(C)C | C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCC(CCCC(=O)OC(COC1=C2C(C=C(OC2=CC=C1)C(=O)O)=O)COC1=C2C(C=C(OC2=CC=C1)C(=O)O)=O)COC(CCCCCCCCCCCCCCCCC)=O.C(C)(=O)O>>N[C@@H](C(C)C)C(=O)OCC(CCCC(=O)OC(COC1=C2C(C=C(OC2=CC=C1)C(=O)O)=O)COC1=C2C(C=C(OC2=CC=C1)C(=O)O)=O)COC(CCCCCCCCCCCCCCCCC)=O | c1ccc(C(c2ccccc2)(c2ccccc2)[NH:67][C@H:66]([C:64]([O:63][CH2:62][CH:22]([CH2:21][O:20][C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19])[CH2:23][CH2:24][CH2:25][C:26](=[O:27])[O:28][CH:29]([CH2:30][O:31][c:32]2[cH:33][cH:34][cH... | CCCCCCCCCCCCCCCCCC(=O)OCC(CCCC(=O)OC(COc1cccc2oc(C(=O)O)cc(=O)c12)COc1cccc2oc(C(=O)O)cc(=O)c12)COC(=O)[C@@H](NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(C)C | CCCCCCCCCCCCCCCCCC(=O)OCC(CCCC(=O)OC(COc1cccc2oc(C(=O)O)cc(=O)c12)COc1cccc2oc(C(=O)O)cc(=O)c12)COC(=O)[C@@H](N)C(C)C | null | null | C(C)(=O)OCC | Deprotection | OtherReaction | 7c27519660e9b0607fb80b9d32b9bfde8e19f5eec1a916a21370255e79658eb1 | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | O=c1ccoc2cccc(OCCCOc3cccc4occc(=O)c34)c12 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[NH;D2;+0:7]-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6])-[NH2;D1;+0:7] | null | [] | null | null | 2 | HOUR | Dibenzyl ester of 2-[5-(N-trityl-L-valyloxymethyl)-6-stearoyloxyhexanoyloxy]-1,3-bis-(2-carboxychromon-5-yloxy)propane (238 mg, (0.17 mmol) was dissolved in ethyl acetate (1.5 ml). To the solution was added 80% acetic acid (10 ml). After two hr, the solution was evaporated and purified by column chromatography to yield... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccc2ccccc2o1.c1ccc2ccccc2o1 | Other | C(C)(=O)OCC | null | 2 | CCCCCCCCCCCCCCCCCC(=O)OCC(CCCC(=O)OC(COc1cccc2oc(C(=O)O)cc(=O)c12)COc1cccc2oc(C(=O)O)cc(=O)c12)COC(=O)[C@@H](NC(c1ccccc1)(c1ccccc1)c1ccccc1)C(C)C>C(C)(=O)OCC>CCCCCCCCCCCCCCCCCC(=O)OCC(CCCC(=O)OC(COc1cccc2oc(C(=O)O)cc(=O)c12)COc1cccc2oc(C(=O)O)cc(=O)c12)COC(=O)[C@@H](N)C(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d724c41f548a46419996ecb82186a486 | C=CCC(C)(C)C(=O)O.COc1ccc(CCl)cc1>>C=CCC(C)(C)C(=O)OCc1ccc(OC)cc1 | COC1=CC=C(CCl)C=C1.CC(C(=O)O)(CC=C)C.CC(C)([O-])C.[K+]>>CC(C(=O)OCC1=CC=C(C=C1)OC)(CC=C)C | [CH2:1]=[CH:2][CH2:3][C:4]([CH3:5])([CH3:6])[C:7](=[O:8])[OH:9].Cl[CH2:10][c:11]1[cH:12][cH:13][c:14]([O:15][CH3:16])[cH:17][cH:18]1>>[CH2:1]=[CH:2][CH2:3][C:4]([CH3:5])([CH3:6])[C:7](=[O:8])[O:9][CH2:10][c:11]1[cH:12][cH:13][c:14]([O:15][CH3:16])[cH:17][cH:18]1 | C=CCC(C)(C)C(=O)O.COc1ccc(CCl)cc1 | C=CCC(C)(C)C(=O)OCc1ccc(OC)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]>>[C:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 95.8 | [{"value": 95.8, "product": "CC(C(=O)OCC1=CC=C(C=C1)OC)(CC=C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 1 | HOUR | To a solution of 2,2-dimethyl-4-pentenoic acid (11.5 g, 90 mmol) in DMF (250 mL) at room temperature, was added potassium tert-butoxide (11.1 g, 99 mmol). The reaction mixture was stirred at 60° C. for 1 h. 4-Methoxybenzylchloride (16.9 g, 108 mmol) was added and the reaction mixture was stirred at 60° C. for 4 h. The ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | c1ccccc1 | HCl | CN(C)C=O | 60 | 1 | C=CCC(C)(C)C(=O)O.COc1ccc(CCl)cc1>CN(C)C=O>C=CCC(C)(C)C(=O)OCc1ccc(OC)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5c74924108fa4208806b46644550275d | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.COc1ccc(COC(=O)C(C)(C)CC(O)CO)cc1>>COc1ccc(COC(=O)C(C)(C)CC(O)COC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)cc1 | C1CCC(CC1)N=C=NC2CCCCC2.OC(CC(C(=O)OCC1=CC=C(C=C1)OC)(C)C)CO.C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)O>>C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCC(CC(C(=O)OCC1=CC=C(C=C1)OC)(C)C)O | O[C:19](=[O:20])[C@@H:21]([NH:22][C:23](=[O:24])[O:25][CH2:26][c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1)[CH:33]([CH3:34])[CH3:35].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][C:9](=[O:10])[C:11]([CH3:12])([CH3:13])[CH2:14][CH:15]([OH:16])[CH2:17][OH:18])[cH:36][cH:37]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7]... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.COc1ccc(COC(=O)C(C)(C)CC(O)CO)cc1 | COc1ccc(COC(=O)C(C)(C)CC(O)COC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)cc1 | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Acylation | Esterification of Carboxylic Acids | d9bd78214ee7dbc907e499722ae01849a72d188753963443e5df9fe42c31c43b | 3652e761944e8ef7ee40675a156c8ae39909c72166786934d88652debf2ec1ac | O=C(CCCCOC(=O)CNC(=O)OCc1ccccc1)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[C:9]-[OH;D1;+0:10]>>[C:8]-[C:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7] | 66.8 | [{"value": 66.8, "product": "C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCC(CC(C(=O)OCC1=CC=C(C=C1)OC)(C)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a mixture of DCC (14.8 g, 72 mmol), DMAP (0.88 g, 7.2 mmol) and 4-methoxybenzyl 4,5-dihydroxy-2,2-dimethyl-valerate (20.3 g, 72 mmol) in CH2Cl2 (400 mL) at 0° C., was added dropwise a solution of N-CBz-L-valine (16.2 g, 65 mmol) in CH2Cl2 (100 mL). After 1 h at 0° C., the temperature of the reaction mixture was allo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1.c1ccccc1 | HO- | CN(C)C=1C=CN=CC1.C(Cl)Cl | null | 1 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.COc1ccc(COC(=O)C(C)(C)CC(O)CO)cc1>CN(C)C=1C=CN=CC1.C(Cl)Cl>COc1ccc(COC(=O)C(C)(C)CC(O)COC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c5868d4c7e8b48e6b69e76f48e9676a0 | CCCCCCCCCCCCCCCCCC(=O)Cl.COc1ccc(COC(=O)C(C)(C)CC(O)COC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)cc1>>CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(C)(C)C(=O)OCc1ccc(OC)cc1 | C(CCCCCCCCCCCCCCCCC)(=O)Cl.C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCC(CC(C(=O)OCC1=CC=C(C=C1)OC)(C)C)O.N1=CC=CC=C1>>C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCC(CC(C(=O)OCC1=CC=C(C=C1)OC)(C)C)OC(CCCCCCCCCCCCCCCCC)=O | Cl[C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19].[OH:20][CH:21]([CH2:22][O:23][C:24](=[O:25])[C@@H:26]([NH:27][C:28](=[O:29])[O:30][CH2:31][c:32]1[cH:33][cH:34][cH:35][cH:36][cH:37]1)[CH:38]([CH3:39])[CH3:40])[CH2:41][C:42](... | CCCCCCCCCCCCCCCCCC(=O)Cl.COc1ccc(COC(=O)C(C)(C)CC(O)COC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)cc1 | CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(C)(C)C(=O)OCc1ccc(OC)cc1 | null | null | C(Cl)Cl | Acylation | Schotten-Baumann to ester | 27b76e29491fa7db5375755e15223de884a194f57a493147db0b5495ea981908 | d47ab90ace9b5dcd818151c10aae400dcf599f5a3476072b8dfedc474e97c335 | O=C(CCCCOC(=O)CNC(=O)OCc1ccccc1)OCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6](-[C:7])-[OH;D1;+0:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:8]-[C:6](-[C:5])-[C:7] | 87 | [{"value": 87.0, "product": "C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCC(CC(C(=O)OCC1=CC=C(C=C1)OC)(C)C)OC(CCCCCCCCCCCCCCCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a mixture of 4-methoxybenzyl 5-(N-CBz-L-valyloxy)-4-hydroxy-2,2-dimethylvalerate (20.6 g, 40 mmol), Pyridine (31.6 g, 400 mmol) in CH2Cl2 (500 mL) at 0° C., was added dropwise a solution of stearoyl chloride (18.2 g, 60 mmol) in CH2Cl2 (100 mL). After 1 h at 0° C., the temperature of the reaction mixture was allowed... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary alcohol | Ester | null | null | c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | 1 | CCCCCCCCCCCCCCCCCC(=O)Cl.COc1ccc(COC(=O)C(C)(C)CC(O)COC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)cc1>C(Cl)Cl>CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(C)(C)C(=O)OCc1ccc(OC)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a7ededce6024461881f8d795fffc9c5d | CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(C)(C)C(=O)OCc1ccc(OC)cc1>>CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(C)(C)C(=O)O | C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCC(CC(C(=O)OCC1=CC=C(C=C1)OC)(C)C)OC(CCCCCCCCCCCCCCCCC)=O.FC(C(=O)O)(F)F>>C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCC(CC(C(=O)O)(C)C)OC(CCCCCCCCCCCCCCCCC)=O | COc1ccc(C[O:47][C:45]([C:42]([CH2:41][CH:21]([O:20][C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19])[CH2:22][O:23][C:24](=[O:25])[C@@H:26]([NH:27][C:28](=[O:29])[O:30][CH2:31][c:32]2[cH:33][cH:34][cH:35][cH:36][cH:37]2)[CH:38]... | CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(C)(C)C(=O)OCc1ccc(OC)cc1 | CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(C)(C)C(=O)O | null | null | C(Cl)Cl | Reduction | Ester saponification (alkyl deprotection) | af4a00273af84ecb3074b1842201a78a3aac9a41d2050132ad8c8c1c9d796dee | 8d997f8b7994d8c9cf23425771b3f80d4d4830ac4e3d6552f381db244a5a65c5 | c1ccccc1 | C-O-c1:c:c:c(-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]):c:c:1>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 90.6 | [{"value": 90.6, "product": "C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCC(CC(C(=O)O)(C)C)OC(CCCCCCCCCCCCCCCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 4-methoxybenzyl 5-(N-CBz-L-valyloxy)-4-stearoyloxy-2,2-dimethylvalerate (25.5 g, 33 mmol) in CH2Cl2 (400 mL) at room temperature, was added trifluoroacetic acid (40 mL). After 1 h at room temperature, the reaction mixture was concentrated under reduced pressure. The crude product was column chromatogra... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Carboxylic acid | c1ccccc1 | null | c1ccccc1 | HO- | C(Cl)Cl | null | 1 | CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(C)(C)C(=O)OCc1ccc(OC)cc1>C(Cl)Cl>CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(C)(C)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-399792a547124b669ccefd5d5840b57c | CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(C)(C)C(=O)O.ClCI>>CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(C)(C)C(=O)OCCl | ClCI.C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCC(CC(C(=O)O)(C)C)OC(CCCCCCCCCCCCCCCCC)=O.[OH-].C(CCC)[N+](CCCC)(CCCC)CCCC>>C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCC(CC(C(=O)OCCl)(C)C)OC(CCCCCCCCCCCCCCCCC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH:21]([CH2:22][O:23][C:24](=[O:25])[C@@H:26]([NH:27][C:28](=[O:29])[O:30][CH2:31][c:32]1[cH:33][cH:34][cH:35][cH:36][cH:37]1)[CH:38]([CH3:39])[CH3:40])[CH2:41][C:42]([CH3... | CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(C)(C)C(=O)O.ClCI | CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(C)(C)C(=O)OCCl | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2f16a3cac6d3c4085515a42267501b7a0eef68b042dbe72a334a9b3dd1458b44 | 20b23d23df2ca888376bbfdf646588e67491b315935b071cb9ba310488e4ee8f | c1ccccc1 | I-[CH2;D2;+0:1]-[Cl;D1;H0:2].[C:3]-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6]>>[C:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[Cl;D1;H0:2] | 64.5 | [{"value": 64.5, "product": "C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCC(CC(C(=O)OCCl)(C)C)OC(CCCCCCCCCCCCCCCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a solution of 5-(N-CBz-L-valyloxy)-4-stearoyloxy-2,2-dimethylvaleric acid (16.0 g, 24 mmol) in dioxane (500 mL), was added dropwise a 40% aqueous solution of tetrabutylammonium hydroxide (14.3 mL). After stirring for 5 min, the solution was evaporated to dryness through co-evaporation with dioxane and toluene. The r... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carboxylic acid | Primary halide.Ester | null | null | c1ccccc1 | HI | O1CCOCC1 | null | 0.083333 | CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(C)(C)C(=O)O.ClCI>O1CCOCC1>CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(C)(C)C(=O)OCCl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-15c743d1885e41eda0691f710331006e | CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(C)(C)C(=O)OCCl.[I-]>>CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(C)(C)C(=O)OCI | C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCC(CC(C(=O)OCCl)(C)C)OC(CCCCCCCCCCCCCCCCC)=O.[I-].[Na+]>>C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCC(CC(C(=O)OCI)(C)C)OC(CCCCCCCCCCCCCCCCC)=O | Cl[CH2:48][O:47][C:45]([C:42]([CH2:41][CH:21]([O:20][C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19])[CH2:22][O:23][C:24](=[O:25])[C@@H:26]([NH:27][C:28](=[O:29])[O:30][CH2:31][c:32]1[cH:33][cH:34][cH:35][cH:36][cH:37]1)[CH:38... | CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(C)(C)C(=O)OCCl.[I-] | CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(C)(C)C(=O)OCI | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | 10bee13c50a4ba107934328c21250869f883899fc8944cf8a0ebee609aa1691d | fe69d77c5ffecf9aa0236c58528d10fdb0294a434868899e60e585d0629b72f9 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5].[I-;H0;D0:6]>>[C:4]-[C:3](=[O;D1;H0:5])-[#8:2]-[CH2;D2;+0:1]-[I;H0;D1;+0:6] | 88.9 | [{"value": 88.9, "product": "C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCC(CC(C(=O)OCI)(C)C)OC(CCCCCCCCCCCCCCCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 4 | HOUR | To a solution of chloromethyl 5-(N-CBz-L-valyloxy)-4-stearoyloxy-2,2-dimethylvalerate (7.8 g, 11 mmol) in acetonitrile (100 mL), was added sodium iodide (6.5 g, 44 mmol). The solution was stirred for 4 h at 60° C. The resulting suspension was filtered and the filtrate was evaporated. The residue was dissolved in CH2Cl2... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Primary halide | null | null | c1ccccc1 | Other | C(C)#N | 60 | 4 | CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(C)(C)C(=O)OCCl.[I-]>C(C)#N>CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(C)(C)C(=O)OCI |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6b322b3158af4852972ea8cd818913d4 | CC(I)OC(=O)OC(COC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C)COC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C.CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(COC(C)=O)CS[C@H]12)c1csc(N)n1>>CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)OC(C)OC(=O)OC(COC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C)COC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C)=C(COC(C)=O)CS[C@H]12)c1csc(N)n1 | C(OC(COC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O)COC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O)(OC(C)I)=O.CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N\OC)/C3=CSC(=N3)N)SC1)C(=O)[O-].[Na+]>>C(C)(=O)OCC=1CS[C@H]2N(C1C(=O)OC(C)OC(=O)OC(COC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O)COC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O)C([C@H]2NC(\C(=N/OC)\C=2N=C(SC2)... | I[CH:16]([CH3:17])[O:18][C:19](=[O:20])[O:21][CH:22]([CH2:23][O:24][C:25](=[O:26])[C@@H:27]([NH:28][C:29](=[O:30])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35])[CH:36]([CH3:37])[CH3:38])[CH2:39][O:40][C:41](=[O:42])[C@@H:43]([NH:44][C:45](=[O:46])[O:47][C:48]([CH3:49])([CH3:50])[CH3:51])[CH:52]([CH3:53])[CH3:54].[CH3:1][O:2... | CC(I)OC(=O)OC(COC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C)COC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C.CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(COC(C)=O)CS[C@H]12)c1csc(N)n1 | CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)OC(C)OC(=O)OC(COC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C)COC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C)=C(COC(C)=O)CS[C@H]12)c1csc(N)n1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 325232c11a00d4b4ffa64d80925dcb5ba322ee1152974e63432458179bde8125 | 218bc40d86dd35ef0e94658f95ea11dc9d21baab063ffc4b6241b0e1ab8da5fa | N=C(C(=O)N[C@@H]1C(=O)N2C=CCS[C@H]12)c1cscn1 | I-[CH;D3;+0:1](-[C;D1;H3:2])-[#8:3]-[C:4](-[#8:5])=[O;D1;H0:6].[#16:7]-[C:8]-[C:9](-[C:10])=[C:11](-[C:12](-[O-;H0;D1:13])=[O;D1;H0:14])-[#7:15]-[C:16]=[O;D1;H0:17]>>[#16:7]-[C:8]-[C:9](-[C:10])=[C:11](-[C:12](=[O;D1;H0:14])-[O;H0;D2;+0:13]-[CH;D3;+0:1](-[C;D1;H3:2])-[#8:3]-[C:4](-[#8:5])=[O;D1;H0:6])-[#7:15]-[C:16]=[O... | null | [] | null | null | null | null | A solution of 1,3-bis(N-tert-butoxycarbonyl-L-valyloxy)-2-propyl 1-iodoethyl carbonate (0.156 mmol) and cefotaxime sodium (67.8 mg, 0.142 mmol) in 3.2 mL dry N,N′-dimethylformamide was stirred under argon for 22 h. The reaction mixture was concentrated and subjected to column chromatography (silica, 2/1 petroleum ether... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Carbonic Ester | Carbonic Ester.Ester | null | null | C1=CN2CC[C@H]2SC1.c1cscn1 | I- | CN(C)C=O | null | null | CC(I)OC(=O)OC(COC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C)COC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C.CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(COC(C)=O)CS[C@H]12)c1csc(N)n1>CN(C)C=O>CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)OC(C)OC(=O)OC(COC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C)COC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C)=C(COC(C)=O)CS[C@H]12)c1csc(N)n... |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-38fb386f9aab4682864b9e09599d2375 | BrCc1ccccc1.O=C(O)c1ccc(O)cc1>>O=C(O)c1ccc(OCc2ccccc2)cc1 | C(C1=CC=CC=C1)Br.[OH-].[Na+].OC1=CC=C(C(=O)O)C=C1.CC(C)([O-])C.[K+]>>C(C1=CC=CC=C1)OC1=CC=C(C(=O)O)C=C1 | Br[CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:16][cH:17]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1 | BrCc1ccccc1.O=C(O)c1ccc(O)cc1 | O=C(O)c1ccc(OCc2ccccc2)cc1 | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | null | [] | null | null | 1 | HOUR | To a solution of 4-hydroxybenzoic acid (6.9 g, 50 mmole) in 150 ml DMF was added potassium tert.-butoxide (12.34 g, 110 mmole) and the mixture was stirred at room temperature for one hour. Benzyl bromide (20.5 g, 120 mmole) was added and the mixture was stirred for two days at room temperature. The mixture was evaporat... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | O.CN(C)C=O | null | 1 | BrCc1ccccc1.O=C(O)c1ccc(O)cc1>O.CN(C)C=O>O=C(O)c1ccc(OCc2ccccc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cdce5cea1e764f75aff953faac4e8aaa | O=C(O)c1ccc(OCc2ccccc2)cc1.O=S(Cl)Cl>>O=C(Cl)c1ccc(OCc2ccccc2)cc1 | S(=O)(Cl)Cl.C(C1=CC=CC=C1)OC1=CC=C(C(=O)O)C=C1>>C(C1=CC=CC=C1)OC1=CC=C(C(=O)Cl)C=C1 | O[C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1.O=S(Cl)[Cl:3]>>[O:1]=[C:2]([Cl:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1 | O=C(O)c1ccc(OCc2ccccc2)cc1.O=S(Cl)Cl | O=C(Cl)c1ccc(OCc2ccccc2)cc1 | null | CN(C)C=O | ClCCl | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccc(COc2ccccc2)cc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | To a mixture of 4-benzyloxybenzoic acid (2.28 g, 10 mmole) in 20 ml dried dichloromethane were added five drops of DMF and 2.5 ml thionyl chloride. The mixture was refluxed for three hours and evaporated under reduced pressure. Yield: 2.45 g=100%
Conditions: See reaction.notes.procedure_details.
Workup: The mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1.c1ccccc1 | HCl | CN(C)C=O.ClCCl | null | null | O=C(O)c1ccc(OCc2ccccc2)cc1.O=S(Cl)Cl>CN(C)C=O.ClCCl>O=C(Cl)c1ccc(OCc2ccccc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d4fd6dbc46e24ce09d40bf732467c07c | COc1ccc(COc2ccc(C(=O)O)cc2)cc1.ClCI>>COc1ccc(COc2ccc(C(=O)OCCl)cc2)cc1 | ICCl.COC1=CC=C(COC2=CC=C(C(=O)O)C=C2)C=C1.[OH-].C(CCC)[N+](CCCC)(CCCC)CCCC>>COC1=CC=C(COC2=CC=C(C(=O)OCCl)C=C2)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([C:13](=[O:14])[OH:15])[cH:18][cH:19]2)[cH:20][cH:21]1.I[CH2:16][Cl:17]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([C:13](=[O:14])[O:15][CH2:16][Cl:17])[cH:18][cH:19]2)[cH:20][cH:21]1 | COc1ccc(COc2ccc(C(=O)O)cc2)cc1.ClCI | COc1ccc(COc2ccc(C(=O)OCCl)cc2)cc1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2f16a3cac6d3c4085515a42267501b7a0eef68b042dbe72a334a9b3dd1458b44 | 20b23d23df2ca888376bbfdf646588e67491b315935b071cb9ba310488e4ee8f | c1ccc(COc2ccccc2)cc1 | I-[CH2;D2;+0:1]-[Cl;D1;H0:2].[O;D1;H0:3]=[C:4](-[OH;D1;+0:5])-[c:6]>>[Cl;D1;H0:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[C:4](=[O;D1;H0:3])-[c:6] | null | [] | null | null | 2 | HOUR | To a solution of 4-(4-methoxybenzyloxy) benzoic acid (5.16 g, 20 mmole) in 100 ml 1,4-dioxane was added a 40% solution of tetrabutylammonium hydroxide (14.27 g, 22 mmole) and the mixture was stirred 2 hours at room temperature. The mixture was evaporated under reduced pressure and co-evaporated two times with 1,4-dioxa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carboxylic acid | Primary halide.Ester | null | null | c1ccccc1.c1ccccc1 | HI | O1CCOCC1 | null | 2 | COc1ccc(COc2ccc(C(=O)O)cc2)cc1.ClCI>O1CCOCC1>COc1ccc(COc2ccc(C(=O)OCCl)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c4b7982cbe3b48a4b252de5aac9e76dd | BrCc1ccccc1.Oc1ccc2cccc(O)c2n1>>Oc1ccc2cccc(OCc3ccccc3)c2n1 | O.C([O-])([O-])=O.[K+].[K+].N1=C(C=CC2=CC=CC(=C12)O)O.C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)OC=1C=CC=C2C=CC(=NC12)O | Br[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[OH:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][c:9]([OH:10])[c:18]2[n:19]1>>[OH:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][c:9]([O:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[c:18]2[n:19]1 | BrCc1ccccc1.Oc1ccc2cccc(O)c2n1 | Oc1ccc2cccc(OCc3ccccc3)c2n1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2cccc3cccnc23)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8](:[c:9]):[#7;a:10]:[c:11]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8](:[c:9]):[#7;a:10]:[c:11]):[c:4] | 68.3 | [{"value": 68.3, "product": "C(C1=CC=CC=C1)OC=1C=CC=C2C=CC(=NC12)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | 5.5 | HOUR | 2,8-Quinolinediol (133.3 g, 0.827 mol) was dissolved in 800 mL of anhydrous DMF under an atmosphere of dry N2. To this solution was added potassium carbonate (183 g, 1.32 mol) followed by benzyl bromide (110 mL, 0.909 mol) and the solution was then warmed up to 65° C. and reacted at this temperature overnight. The reac... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2ncccc2c1.c1ccccc1 | HBr | CN(C)C=O | 65 | 5.5 | BrCc1ccccc1.Oc1ccc2cccc(O)c2n1>CN(C)C=O>Oc1ccc2cccc(OCc3ccccc3)c2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-eb1da8f03dc8435a8d46e343d236c3e5 | CC(C)(C)[Si](C)(C)Oc1cccc2ccc(OS(=O)(=O)C(F)(F)F)nc12.COc1ccc(N)c([N+](=O)[O-])c1>>COc1ccc(Nc2ccc3cccc(O[Si](C)(C)C(C)(C)C)c3n2)c([N+](=O)[O-])c1 | C(C)(C)(C)[Si](OC=1C=CC=C2C=CC(=NC12)OS(=O)(=O)C(F)(F)F)(C)C.COC1=CC(=C(N)C=C1)[N+](=O)[O-].C([O-])([O-])=O.[Cs+].[Cs+]>>C(C)(C)(C)[Si](OC=1C=CC=C2C=CC(=NC12)NC1=C(C=C(C=C1)OC)[N+](=O)[O-])(C)C | O=S(=O)(O[c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][cH:14][c:15]([O:16][Si:17]([CH3:18])([CH3:19])[C:20]([CH3:21])([CH3:22])[CH3:23])[c:24]2[n:25]1)C(F)(F)F.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[c:26]([N+:27](=[O:28])[O-:29])[cH:30]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[cH:9][cH:10][c:11]3[cH:12][cH:1... | CC(C)(C)[Si](C)(C)Oc1cccc2ccc(OS(=O)(=O)C(F)(F)F)nc12.COc1ccc(N)c([N+](=O)[O-])c1 | COc1ccc(Nc2ccc3cccc(O[Si](C)(C)C(C)(C)C)c3n2)c([N+](=O)[O-])c1 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | O1CCOCC1 | Functional Group Addition | Alkylation of amines | 48bc92bfc8dca67af15ad25c7ecc89c81e22d691bfcad39fbd80df7933404270 | 7c347a282259bf554bd21956190d66b30039de421f343577b1bd262e2f3c9b78 | c1ccc(Nc2ccc3ccccc3n2)cc1 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:2]:[c:3] | null | [] | 100 | CELSIUS | null | null | Trifluoro-methanesulfonic acid 8-(tert-butyl-dimethyl-silanyloxy)-quinolin-2-yl ester B (9.81 g, 24.1 mmol) and 4-methoxy-2-nitroaniline (4.86 g, 28.9 mmol) were dissolved in 100 mL of dioxane under an atmosphere of dry N2. To this solution was added (11.0 g, 33.7 mmol) cesium carbonate (Cs2CO3), (900 mg, 1.45 mmol) ra... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1 | TfOH.HO- | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O1CCOCC1 | 100 | null | CC(C)(C)[Si](C)(C)Oc1cccc2ccc(OS(=O)(=O)C(F)(F)F)nc12.COc1ccc(N)c([N+](=O)[O-])c1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O1CCOCC1>COc1ccc(Nc2ccc3cccc(O[Si](C)(C)C(C)(C)C)c3n2)c([N+](=O)[O-])c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-125c40e566ad482d82bdf2be9a243c46 | COc1ccc(Nc2ccc3cccc(O[Si](C)(C)C(C)(C)C)c3n2)c([N+](=O)[O-])c1>>COc1ccc(Nc2ccc3cccc(O[Si](C)(C)C(C)(C)C)c3n2)c(N)c1 | C(C)(C)(C)[Si](OC=1C=CC=C2C=CC(=NC12)NC1=C(C=C(C=C1)OC)[N+](=O)[O-])(C)C.C1CCOC1.NN>>C(C)(C)(C)[Si](OC=1C=CC=C2C=CC(=NC12)NC=1C(=CC(=CC1)OC)N)(C)C | O=[N+:27]([O-])[c:26]1[c:6]([NH:7][c:8]2[cH:9][cH:10][c:11]3[cH:12][cH:13][cH:14][c:15]([O:16][Si:17]([CH3:18])([CH3:19])[C:20]([CH3:21])([CH3:22])[CH3:23])[c:24]3[n:25]2)[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[cH:9][cH:10][c:11]3[cH:12][cH:13][cH:14][c:15]([O:16][Si:17... | COc1ccc(Nc2ccc3cccc(O[Si](C)(C)C(C)(C)C)c3n2)c([N+](=O)[O-])c1 | COc1ccc(Nc2ccc3cccc(O[Si](C)(C)C(C)(C)C)c3n2)c(N)c1 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Nc2ccc3ccccc3n2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 2 | HOUR | ([8-(tert-Butyl-dimethyl-silanyloxy)-quinolin-2-yl]-(4-methoxy-2-nitro-phenyl)-amine C (21.9 g, 51.3 mmol) was dissolved in 200 mL ethanol (EtOH) and 70 mL of THF under an atmosphere of dry N2. To this solution was added 10% palladium on carbon (2.18 g) followed by the dropwise addition of 10 mL of anhydrous hydrazine.... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2ncccc2c1 | Other | [Pd].C(C)O | null | 2 | COc1ccc(Nc2ccc3cccc(O[Si](C)(C)C(C)(C)C)c3n2)c([N+](=O)[O-])c1>[Pd].C(C)O>COc1ccc(Nc2ccc3cccc(O[Si](C)(C)C(C)(C)C)c3n2)c(N)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ec23b57cce764bea9aa62a3e7a47e687 | COc1ccc(Nc2ccc3cccc(O[Si](C)(C)C(C)(C)C)c3n2)c(N)c1>>COc1ccc2c(c1)ncn2-c1ccc2cccc(O)c2n1 | C(C)(C)(C)[Si](OC=1C=CC=C2C=CC(=NC12)NC=1C(=CC(=CC1)OC)N)(C)C.C(C)(=O)O.C(=N)N>>COC1=CC2=C(N(C=N2)C2=NC3=C(C=CC=C3C=C2)O)C=C1 | CC(C)(C)[Si](C)(C)[O:20][c:19]1[cH:18][cH:17][cH:16][c:15]2[cH:14][cH:13][c:12]([NH:11][c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8][c:7]3[NH2:9])[n:22][c:21]21>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[n:9][cH:10][n:11]2-[c:12]1[cH:13][cH:14][c:15]2[cH:16][cH:17][cH:18][c:19]([OH:20])[c:21]2[n:22]1 | COc1ccc(Nc2ccc3cccc(O[Si](C)(C)C(C)(C)C)c3n2)c(N)c1 | COc1ccc2c(c1)ncn2-c1ccc2cccc(O)c2n1 | null | null | COCCO | Aromatic Heterocycle Formation | OtherReaction | f10f6ae5232ebd73b5df3b12a04f1ba735f991c2cb664093fc28752ed891889e | 7b5992d8e7a735d6b5213a007f2bb47d64fbc213d57bb8b8c1d9723dafba63fb | c1ccc2nc(-n3cnc4ccccc43)ccc2c1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]1:[#7;a:5]:[c;H0;D3;+0:6](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10](-[NH2;D1;+0:11]):[c:12]):[c:13]:[c:14]:[c:15]:1>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4]1:[#7;a:5]:[c;H0;D3;+0:6](-[n;H0;D3;+0:7]2:[c:16]:[n;H0;D2;+0:11]:[c:10](:[c:12]):[c:8]:2:[c:9]):[c:13]:[c:14]:[c:15]:1 | null | [] | 125 | CELSIUS | null | null | N1-[8-(tert-Butyl-dimethyl-silanyloxy)-quinolin-2-yl]-4-methoxy-benzene-1,2-diamine D (18.3 g, 46.1 mmol) was dissolved in 40 mL of 2-methoxyethanol under an atmosphere of dry N2. To this solution was added formamidine acetate (5.28 g, 50.7 mmol) and the reaction mixture was heated to 125° C. and reacted at this temper... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine.TMS ether protective group | Aromatic alcohol | c1ccccc1 | c1ccc2nc[nH]c2c1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1 | Other | COCCO | 125 | null | COc1ccc(Nc2ccc3cccc(O[Si](C)(C)C(C)(C)C)c3n2)c(N)c1>COCCO>COc1ccc2c(c1)ncn2-c1ccc2cccc(O)c2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d49861d3a01e4b57b560f40d8eaa5b6e | CC(C)(C)OC(=O)NC1CCNCC1.COc1ccc2c(c1)ncn2-c1ccc2cccc(OS(=O)(=O)C(F)(F)F)c2n1>>COc1ccc2c(c1)ncn2-c1ccc2cccc(N3CCC(NC(=O)OC(C)(C)C)CC3)c2n1 | COC1=CC2=C(N(C=N2)C2=NC3=C(C=CC=C3C=C2)OS(=O)(=O)C(F)(F)F)C=C1.C(C)(C)(C)OC(NC1CCNCC1)=O.C=1C=CC(=CC1)P(C=2C=CC=CC2)C3=CC=C4C=CC=CC4=C3C5=C6C=CC=CC6=CC=C5P(C=7C=CC=CC7)C=8C=CC=CC8.C(=O)([O-])[O-].[Cs+].[Cs+]>>C(C)(C)(C)OC(NC1CCN(CC1)C=1C=CC=C2C=CC(=NC12)N1C=NC2=C1C=CC(=C2)OC)=O | [NH:20]1[CH2:21][CH2:22][CH:23]([NH:24][C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[CH2:32][CH2:33]1.O=S(=O)(O[c:19]1[cH:18][cH:17][cH:16][c:15]2[cH:14][cH:13][c:12](-[n:11]3[c:6]4[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8][c:7]4[n:9][cH:10]3)[n:35][c:34]21)C(F)(F)F>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:... | CC(C)(C)OC(=O)NC1CCNCC1.COc1ccc2c(c1)ncn2-c1ccc2cccc(OS(=O)(=O)C(F)(F)F)c2n1 | COc1ccc2c(c1)ncn2-c1ccc2cccc(N3CCC(NC(=O)OC(C)(C)C)CC3)c2n1 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | O1CCOCC1 | Heteroatom Alkylation and Arylation | Alkylation of amines | 38b20d726065366c6b7c36d52ac510496ac451d245f12c3a9631b4667a60cf1b | 9a1a0c2e1b87bdf69534c723b7058cd90b31cce176c7a3bc658b2756600b117c | c1cc(N2CCCCC2)c2nc(-n3cnc4ccccc43)ccc2c1 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7])-[C:11]-[C:12] | null | [] | null | null | null | null | Trifluoro-methanesulfonic acid 2-(5-methoxy-benzoimidazol-1-yl)-quinolin-8-yl ester F (15.0 9, 35.4 mmol) and piperidin-4-yl-carbamic acid tert-butyl ester (14.2 9, 70.9 mmol) were dissolved in 200 mL of dioxane under an atmosphere of dry N2. To this solution was added Cs2CO3 (16.2 g, 49.6 mmol), racemic-BINAP (1.28 9,... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Secondary amine | Tertiary amine | C1CCNCC1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.C1CC[NH]CC1 | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.C1CC[NH]CC1 | TfOH.HO- | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O1CCOCC1 | null | null | CC(C)(C)OC(=O)NC1CCNCC1.COc1ccc2c(c1)ncn2-c1ccc2cccc(OS(=O)(=O)C(F)(F)F)c2n1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O1CCOCC1>COc1ccc2c(c1)ncn2-c1ccc2cccc(N3CCC(NC(=O)OC(C)(C)C)CC3)c2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-067c9c222567442b89d655c5c7c1f3c7 | COc1ccc2c(c1)ncn2-c1ccc2cccc(N3CCC(NC(=O)OC(C)(C)C)CC3)c2n1>>COc1ccc2c(c1)ncn2-c1ccc2cccc(N3CCC(N)CC3)c2n1 | C(C)(C)(C)OC(NC1CCN(CC1)C=1C=CC=C2C=CC(=NC12)N1C=NC2=C1C=CC(=C2)OC)=O>>COC1=CC2=C(N(C=N2)C2=NC3=C(C=CC=C3C=C2)N2CCC(CC2)N)C=C1 | CC(C)(C)OC(=O)[NH:24][CH:23]1[CH2:22][CH2:21][N:20]([c:19]2[cH:18][cH:17][cH:16][c:15]3[cH:14][cH:13][c:12](-[n:11]4[c:6]5[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8][c:7]5[n:9][cH:10]4)[n:28][c:27]32)[CH2:26][CH2:25]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[n:9][cH:10][n:11]2-[c:12]1[cH:13][cH:14][c:15]2[cH:16][c... | COc1ccc2c(c1)ncn2-c1ccc2cccc(N3CCC(NC(=O)OC(C)(C)C)CC3)c2n1 | COc1ccc2c(c1)ncn2-c1ccc2cccc(N3CCC(N)CC3)c2n1 | null | null | FC(C(=O)O)(F)F | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1cc(N2CCCCC2)c2nc(-n3cnc4ccccc43)ccc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | null | [] | null | null | 15 | MINUTE | {1-[2-(5-Methoxy-benzoimidazol-1-yl)-quinolin-8-yl]-piperidin-4-yl}-carbamic acid tert-butyl ester G (8.40 g, 17.7 mmol) was dissolved in 50 mL of trifluoroacetic acid (TFA) under an atmosphere of dry N2. The reaction mixture was stirred at ambient temperature for 15 minutes after which time it was concentrated under v... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2nc[nH]c2c1.c1ccc2ncccc2c1.C1CC[NH]CC1 | HO- | FC(C(=O)O)(F)F | null | 0.25 | COc1ccc2c(c1)ncn2-c1ccc2cccc(N3CCC(NC(=O)OC(C)(C)C)CC3)c2n1>FC(C(=O)O)(F)F>COc1ccc2c(c1)ncn2-c1ccc2cccc(N3CCC(N)CC3)c2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-257b8285598045b99878fc22fb33fe10 | COc1ccc2c(c1)ncn2-c1ccc2cccc(N3CCC(N)CC3)c2n1>>NC1CCN(c2cccc3ccc(-n4cnc5cc(O)ccc54)nc23)CC1 | COC1=CC2=C(N(C=N2)C2=NC3=C(C=CC=C3C=C2)N2CCC(CC2)N)C=C1.B(Br)(Br)Br.C([O-])([O-])=O.[Na+].[Na+]>>NC1CCN(CC1)C=1C=CC=C2C=CC(=NC12)N1C=NC2=C1C=CC(=C2)O | C[O:20][c:19]1[cH:18][c:17]2[n:16][cH:15][n:14](-[c:13]3[cH:12][cH:11][c:10]4[cH:9][cH:8][cH:7][c:6]([N:5]5[CH2:4][CH2:3][CH:2]([NH2:1])[CH2:27][CH2:26]5)[c:25]4[n:24]3)[c:23]2[cH:22][cH:21]1>>[NH2:1][CH:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][cH:9][c:10]3[cH:11][cH:12][c:13](-[n:14]4[cH:15][n:16][c:17]5[cH:18][c:19]... | COc1ccc2c(c1)ncn2-c1ccc2cccc(N3CCC(N)CC3)c2n1 | NC1CCN(c2cccc3ccc(-n4cnc5cc(O)ccc54)nc23)CC1 | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1cc(N2CCCCC2)c2nc(-n3cnc4ccccc43)ccc2c1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | null | [] | null | null | 8 | HOUR | 1-[2-(5-Methoxy-benzoimidazol-1-yl)-quinolin-8-yl]-piperidin-4-ylamine (500 mg, 1.10 mmol) was dissolved in 10 mL of DCM under an atmosphere of dry N2. To this solution was added boron tribromide (300 mL, 3.30 mmol) and the mixture was stirred overnight at ambient temperature. Then an additional 200 mL of borontribromi... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | C1CC[NH]CC1.c1ccc2ncccc2c1.c1ccc2[nH]cnc2c1 | Other | C(Cl)Cl | null | 8 | COc1ccc2c(c1)ncn2-c1ccc2cccc(N3CCC(N)CC3)c2n1>C(Cl)Cl>NC1CCN(c2cccc3ccc(-n4cnc5cc(O)ccc54)nc23)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-27b9174af8894c0099f32b5b99597a6b | CC(C)(C)OC(=O)NC1CCN(c2cccc3ccc(-n4cnc5cc(O)ccc54)nc23)CC1.CC1CC1>>NC1CCN(c2cccc3ccc(-n4cnc5cc(OCC6CC6)ccc54)nc23)CC1 | C(C)(C)(C)OC(NC1CCN(CC1)C=1C=CC=C2C=CC(=NC12)N1C=NC2=C1C=CC(=C2)O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].[Br-].C1(CC1)C>>C1(CC1)COC1=CC2=C(N(C=N2)C2=NC3=C(C=CC=C3C=C2)N2CCC(CC2)N)C=C1 | CC(C)(C)OC(=O)[NH:1][CH:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][cH:9][c:10]3[cH:11][cH:12][c:13](-[n:14]4[cH:15][n:16][c:17]5[cH:18][c:19]([OH:20])[cH:25][cH:26][c:27]45)[n:28][c:29]23)[CH2:30][CH2:31]1.[CH3:21][CH:22]1[CH2:23][CH2:24]1>>[NH2:1][CH:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][cH:9][c:10]3[cH:11][cH:12][... | CC(C)(C)OC(=O)NC1CCN(c2cccc3ccc(-n4cnc5cc(O)ccc54)nc23)CC1.CC1CC1 | NC1CCN(c2cccc3ccc(-n4cnc5cc(OCC6CC6)ccc54)nc23)CC1 | null | null | CN(C)C=O.C(=O)(C(F)(F)F)O | Heteroatom Alkylation and Arylation | OtherReaction | 67298a1045971ca2d1c2c4a08264298be519a6705e4c76ece9960a69ec97adeb | 0b883927f7edc79439452948c60b3e3e823cd2e0d7a7de605a32caa3f14d2d55 | c1cc(N2CCCCC2)c2nc(-n3cnc4cc(OCC5CC5)ccc43)ccc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4].[#7;a:5]:[c:6]:[c:7]:[c:8](-[OH;D1;+0:9]):[c:10].[CH3;D1;+0:11]-[C:12]1-[C:13]-[C:14]-1>>[#7;a:5]:[c:6]:[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:11]-[C:12]1-[C:13]-[C:14]-1):[c:10].[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | null | [] | 65 | CELSIUS | 4 | HOUR | {1-[2-(5-Hydroxy-benzoimidazol-1-yl)-quinolin-8-yl]-piperidin-4-yl}-carbamic acid tert-butyl ester H (200 mg, 0.435 mmol) was dissolved in 1.5 mL of anhydrous DMF under an atmosphere of dry N2. To this solution was added Cs2CO3 (170 mg, 0.520 mmol) followed by cyclopropyl methane bromide (46 mL, 0.48 mMol). The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Aromatic alcohol.Boc | Ether.Primary amine | null | null | C1CC[NH]CC1.c1ccc2ncccc2c1.c1ccc2[nH]cnc2c1.C1CC1 | HO- | CN(C)C=O.C(=O)(C(F)(F)F)O | 65 | 4 | CC(C)(C)OC(=O)NC1CCN(c2cccc3ccc(-n4cnc5cc(O)ccc54)nc23)CC1.CC1CC1>CN(C)C=O.C(=O)(C(F)(F)F)O>NC1CCN(c2cccc3ccc(-n4cnc5cc(OCC6CC6)ccc54)nc23)CC1 |
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