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-018fd0e1351f4fd09b20fcddd97b4c7a | ord-71828877dd4a46a7a0bca4e4e2ebc272 | COc1ccc2cc(N(C)C)sc2c1>>COc1ccc2c(c1)SC(=O)C2 | CN(C1=CC2=C(S1)C=C(C=C2)OC)C.O1CCCC1.Cl>>COC1=CC2=C(CC(=O)S2)C=C1 | CN(C)[c:10]1[s:9][c:7]2[c:6]([cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]2)[cH:12]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[S:9][C:10](=[O:11])[CH2:12]2 | COc1ccc2cc(N(C)C)sc2c1 | COc1ccc2c(c1)SC(=O)C2 | null | null | null | Miscellaneous | OtherReaction | 7ec91e72ad4514f96d10825f092a3f78fdb6234593bffc93605e8ff2e9a497de | b4305623bf739174ef5934db06197c51126cdafe031b92baeff8df43c46cbb25 | O=C1Cc2ccccc2S1 | C-N(-C)-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c:3](:[c:4]):[c:5](:[c:6]):[s;H0;D2;+0:7]:1>>[O;D1;H0:8]=[C;H0;D3;+0:1]1-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5](:[c:6])-[S;H0;D2;+0:7]-1 | 80 | [{"value": 80.0, "product": "COC1=CC2=C(CC(=O)S2)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To tetrahydrofuran (200 mL) containing 2-dimethylamino-6-methoxybenzo-[b]-thiophene (cf. U.S. Pat. No. 5,420,349) (20.00 g, 96.5 mmol) was added 1N aqueous HCl (200 mL) and the resulting mixture was heated to reflux for 3 h. The mixture was cooled, the layers were separated, and the aqueous layer was extracted with dic... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Carbo-thioester | c1ccc2sccc2c1 | c1ccc2c(c1)CCS2 | c1ccc2c(c1)CCS2 | Other | null | null | null | COc1ccc2cc(N(C)C)sc2c1>>COc1ccc2c(c1)SC(=O)C2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-121fc81dc41c4c78b8c1bded1233dd08 | COc1ccc(C=O)c(O)c1.COc1ccc2c(c1)SC(=O)C2>>COc1ccc2c(c1)OC(=O)C1c3ccc(OC)cc3SC21 | COC1=CC2=C(CC(=O)S2)C=C1.COC=1C=C(C(C=O)=CC1)O>>COC1=CC2=C(C3C(C(O2)=O)C2=C(S3)C=C(C=C2)OC)C=C1 | O=[CH:22][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8][c:7]1[OH:9].[C:10]1(=[O:11])[CH2:12][c:13]2[cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19][c:20]2[S:21]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[O:9][C:10](=[O:11])[CH:12]1[c:13]3[cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19][c:20]3[S:21][CH:22]21 | COc1ccc(C=O)c(O)c1.COc1ccc2c(c1)SC(=O)C2 | COc1ccc2c(c1)OC(=O)C1c3ccc(OC)cc3SC21 | null | C(C)N(CC)CC | C(C)O.C(Cl)Cl | Acylation | OtherReaction | e8fbc487563db87775f9ef5b53c3692d363b1a0498769b64bd7c794649742d9d | 7259bf0e4ba555fe66049920a15c643fe90ace826f32b0be86332a42da8e3e0d | O=C1Oc2ccccc2C2Sc3ccccc3C12 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4](-[OH;D1;+0:5]):[c:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-[CH2;D2;+0:9]-[c:10](:[c:11]):[c:12](:[c:13])-[S;H0;D2;+0:14]-1>>[O;D1;H0:7]=[C;H0;D3;+0:8]1-[O;H0;D2;+0:5]-[c:4](:[c:6]):[c:2](:[c:3])-[CH;D3;+0:1]2-[S;H0;D2;+0:14]-[c:12](:[c:13]):[c:10](:[c:11])-[CH;D3;+0:9]-1-2 | 82.3 | [{"value": 82.0, "product": "COC1=CC2=C(C3C(C(O2)=O)C2=C(S3)C=C(C=C2)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.3, "product": "COC1=CC2=C(C3C(C(O2)=O)C2=C(S3)C=C(C=C2)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a stirred solution of 6-methoxythianaphthen-2-one (see Docket B-9459) (20 g, 111 mmol) in a mixture of ethanol (100 mL) and methylene chloride (50 mL) was added 4-methoxysalicylaldehyde (17.5 g, 115 mmol) followed by triethylamine (567 mg, 784 mL, 5.6 mmol) at room temperature. After 30 min, a solid began to precipi... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Aromatic alcohol.Carbo-thioester | Ester.Monosulfide | c1ccc2c(c1)CCS2 | c1ccc2c(c1)OCC1c3ccccc3SC21 | c1ccc2c(c1)OCC1c3ccccc3SC21 | HO- | C(C)N(CC)CC.C(C)O.C(Cl)Cl | null | 0.5 | COc1ccc(C=O)c(O)c1.COc1ccc2c(c1)SC(=O)C2>C(C)N(CC)CC.C(C)O.C(Cl)Cl>COc1ccc2c(c1)OC(=O)C1c3ccc(OC)cc3SC21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-37dabead809445b0a1f66e1d5ecbac91 | O=S(=O)(Oc1ccc2c(c1)OC(c1ccc(OCCN3CCCCC3)cc1)c1c-2sc2cc(OS(=O)(=O)C(F)(F)F)ccc12)C(F)(F)F>>c1ccc2c(c1)OC(c1ccc(OCCN3CCCCC3)cc1)c1c-2sc2ccccc12 | FC(S(=O)(=O)OC1=CC2=C(C3=C(C(O2)C2=CC=C(C=C2)OCCN2CCCCC2)C2=C(S3)C=C(C=C2)OS(=O)(=O)C(F)(F)F)C=C1)(F)F.C1(=CC=CC=C1)P(C1=CC=CC=C1)CCC.C(=O)O.C(C)N(CC)CC>>N1(CCCCC1)CCOC1=CC=C(C=C1)C1OC2=C(C3=C1C1=C(S3)C=CC=C1)C=CC=C2 | O=S(=O)(O[c:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[O:7][CH:8]([c:9]1[cH:10][cH:11][c:12]([O:13][CH2:14][CH2:15][N:16]3[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]3)[cH:22][cH:23]1)[c:24]1[c:25]-2[s:26][c:27]2[cH:28][c:29](OS(=O)(=O)C(F)(F)F)[cH:30][cH:31][c:32]12)C(F)(F)F>>[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[O:7][CH:8]([c... | O=S(=O)(Oc1ccc2c(c1)OC(c1ccc(OCCN3CCCCC3)cc1)c1c-2sc2cc(OS(=O)(=O)C(F)(F)F)ccc12)C(F)(F)F | c1ccc2c(c1)OC(c1ccc(OCCN3CCCCC3)cc1)c1c-2sc2ccccc12 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | CN(C=O)C | Functional Group Interconversion | OtherReaction | 988f610538c90607221e55e921999ae11469ded1c50793c97c36afbad156792b | e253988a7a940b0d8f3e3d18b6e23b919f63a40009ea6501e6258cd32fcc6067 | c1ccc2c(c1)OC(c1ccc(OCCN3CCCCC3)cc1)c1c-2sc2ccccc12 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]-[#8:6].F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:7]1:[c:8]:[c:9](:[#16;a:10]:[c:11]):[c:12]:[c:13]:[c:14]:1>>[#8:6]-[c:5]:[c:4]:[cH;D2;+0:1]:[c:2]:[c:3].[c:11]:[#16;a:10]:[c:9]1:[c:8]:[cH;D2;+0:7]:[c:14]:[c:13]:[c:12]:1 | 57 | [{"value": 57.0, "product": "N1(CCCCC1)CCOC1=CC=C(C=C1)C1OC2=C(C3=C1C1=C(S3)C=CC=C1)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.0, "product": "N1(CCCCC1)CCOC1=CC=C(C=C1)C1OC2=C(C3=C1C1=C(S3)C=CC=C1)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of the product of Example 6 (780 mg, 1.06 mmol), palladium(II) acetate (42 mg, 0.19 mmol), 1,2-bis(diphenylphosphinopropane (149 mg, 0.36 mmol), formic acid (0.6 mL), and triethylamine (3.0 mL) in anhydrous dimethylformamide (40 mL) was stirred at ambient temperature for 4 d. After concentration, the residue... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Triflate | null | c1ccc2c(c1)OCc1c3ccccc3sc12 | c1ccc2c(c1)OCc1c3ccccc3sc12 | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)OCc1c3ccccc3sc12 | TfOH | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CN(C=O)C | null | null | O=S(=O)(Oc1ccc2c(c1)OC(c1ccc(OCCN3CCCCC3)cc1)c1c-2sc2cc(OS(=O)(=O)C(F)(F)F)ccc12)C(F)(F)F>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CN(C=O)C>c1ccc2c(c1)OC(c1ccc(OCCN3CCCCC3)cc1)c1c-2sc2ccccc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2e1c1509e9854bccbce85b7561bd70a2 | COC(=O)C1C(=O)CCc2cc(OC)ccc21.Oc1cccc(O)c1>>COc1ccc2c(c1)CCc1c-2c(=O)oc2cc(O)ccc12 | O.C(=O)(OC)C1C(CCC2=CC(=CC=C12)OC)=O.C1(O)=CC(O)=CC=C1.P(=O)(Cl)(Cl)Cl>>COC=1C=C2CCC=3C4=C(OC(C3C2=CC1)=O)C=C(C=C4)O | CO[C:13]([CH:12]1[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8][c:7]2[CH2:9][CH2:10][C:11]1=O)=[O:14].[OH:15][c:16]1[cH:17][c:18]([OH:19])[cH:20][cH:21][cH:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][c:11]1[c:12]-2[c:13](=[O:14])[o:15][c:16]2[cH:17][c:18]([OH:19])[cH:20][cH:21][c:22]12 | COC(=O)C1C(=O)CCc2cc(OC)ccc21.Oc1cccc(O)c1 | COc1ccc2c(c1)CCc1c-2c(=O)oc2cc(O)ccc12 | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 4d3aeb8ad75885a43a483a2b4c96b3e7b33057d5f173c48e07c290188732a993 | 89a9e45776dbe9070f40025f4f55f2a7b9907ff5b9cebad1727718d85938e303 | O=c1oc2ccccc2c2c1-c1ccccc1CC2 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3]1-[C;H0;D3;+0:4](=O)-[C:5]-[C:6]-[c:7](:[c:8]):[c;H0;D3;+0:9]-1:[c:10]:[c:11].[OH;D1;+0:12]-[c:13](:[c:14]):[cH;D2;+0:15]:[c:16]:[c:17]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[o;H0;D2;+0:12]:[c:13](:[c:14]):[c;H0;D3;+0:15](:[c:16]:[c:17]):[c;H0;D3;+0:4]2:[c;H0;D3;+0:3]:1-[c;H0;D3;+0:9... | 70.8 | [{"value": 70.8, "product": "COC=1C=C2CCC=3C4=C(OC(C3C2=CC1)=O)C=C(C=C4)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a solution of 1-carbomethoxy-6-methoxy-2-tetralone (see, Colvin, Martin, and Shroot, Chemistry and Industry, 2130 (1966)) (18.0 g, 76.8 mmol) and resorcinol (8.9 g, 80.7 mmol) stirring at ambient temperature in toluene (450 mL) was added phosphorus oxychloride (12.0 g, 7.3 mL, 18.3 mmol) dropwise, and the mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Aromatic alcohol | null | c1ccc2c(c1)CCCC2.c1ccccc1 | c1ccc2c(c1)CCc1c2coc2ccccc12 | c1ccc2c(c1)CCc1c2coc2ccccc12 | HO- | C1(=CC=CC=C1)C | 80 | null | COC(=O)C1C(=O)CCc2cc(OC)ccc21.Oc1cccc(O)c1>C1(=CC=CC=C1)C>COc1ccc2c(c1)CCc1c-2c(=O)oc2cc(O)ccc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9257a86a9c6c4200ba96f6bf32445239 | COc1ccc2c(c1)CCCC2=O.Nc1ccc(O)cc1>>COc1ccc2c(c1)CCCC2=Nc1ccc(O)cc1 | COC=1C=C2CCCC(C2=CC1)=O.OC1=CC=C(N)C=C1>>COC=1C=C2CCCC(C2=CC1)=NC1=CC=C(C=C1)O | O=[C:12]1[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8][c:7]2[CH2:9][CH2:10][CH2:11]1.[NH2:13][c:14]1[cH:15][cH:16][c:17]([OH:18])[cH:19][cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][CH2:11][C:12]2=[N:13][c:14]1[cH:15][cH:16][c:17]([OH:18])[cH:19][cH:20]1 | COc1ccc2c(c1)CCCC2=O.Nc1ccc(O)cc1 | COc1ccc2c(c1)CCCC2=Nc1ccc(O)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Addition of primary amines to ketones/thiocarbonyls | b14ccdda6d8ec09f2623d3e2d2e8e272a424167acc06de88631d823acb29461f | 009cc6a97ebe0dc96c669f0ef59b95bcc20de7cae20b1b648ce8f8fa82309e57 | c1ccc(N=C2CCCc3ccccc32)cc1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C:3]-[C:2]-[C;H0;D3;+0:1](=[N;H0;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:4](:[c:5]):[c:6] | null | [] | 180 | CELSIUS | null | null | A mixture of 6-methoxytetralone (25 g, 142 mmol) and 4-hydroxyaniline (16.3 g, 149 mmol) was heated to 180° C. under a nitrogen stream for 2 h. After cooling to ambient temperature, the solid mass was recrystallized from toluene/methanol: 1H NMR (300 MHz) d 8.15 (d, J=9.7 Hz, 1H), 6.5-7.9 (m, 6H), 3.80 (s, 3H), 2.84 (t... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Substituted imine | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2.c1ccccc1 | HO- | null | 180 | null | COc1ccc2c(c1)CCCC2=O.Nc1ccc(O)cc1>>COc1ccc2c(c1)CCCC2=Nc1ccc(O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3b73803622b24e07932df49f9cb1154a | COc1ccc2c(c1)CN(c1ccc(OCCN3CCCCC3)cc1)c1c-2ccc2cc(OC)ccc12>>Oc1ccc2c(c1)CN(c1ccc(OCCN3CCCCC3)cc1)c1c-2ccc2cc(O)ccc12 | COC=1C=CC2=C(C=CC=3C4=CC=C(C=C4CN(C23)C2=CC=C(C=C2)OCCN2CCCCC2)OC)C1.C(C)S.[Cl-].[Al+3].[Cl-].[Cl-]>>OC=1C=CC2=C(C=CC=3C4=CC=C(C=C4CN(C23)C2=CC=C(C=C2)OCCN2CCCCC2)O)C1 | C[O:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[CH2:8][N:9]([c:10]1[cH:11][cH:12][c:13]([O:14][CH2:15][CH2:16][N:17]3[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]3)[cH:23][cH:24]1)[c:25]1[c:26]-2[cH:27][cH:28][c:29]2[cH:30][c:31]([O:32]C)[cH:33][cH:34][c:35]12>>[OH:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[CH2:8][N:9]([c:10]1[c... | COc1ccc2c(c1)CN(c1ccc(OCCN3CCCCC3)cc1)c1c-2ccc2cc(OC)ccc12 | Oc1ccc2c(c1)CN(c1ccc(OCCN3CCCCC3)cc1)c1c-2ccc2cc(O)ccc12 | null | null | C(Cl)Cl | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | c1ccc2c(c1)CN(c1ccc(OCCN3CCCCC3)cc1)c1c-2ccc2ccccc12 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].C-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8] | 60.5 | [{"value": 60.0, "product": "OC=1C=CC2=C(C=CC=3C4=CC=C(C=C4CN(C23)C2=CC=C(C=C2)OCCN2CCCCC2)O)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.5, "product": "OC=1C=CC2=C(C=CC=3C4=CC=C(C=C4CN(C23)C2=CC=C(C=C2)OCCN2CCCCC2)O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A solution of the product of Example 13 (195 mg, 0.39 mmol) in methylene chloride (25 mL) was treated with ethanethiol (200 mg, 220 mL, 3.2 mmol) and aluminum chloride (320 mg, 2.4 mmol). After stirring for 4 h at ambient temperature, the mixture was quenched carefully with THF (25 mL) and saturated sodium bicarbonate ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)C[NH]c1c3ccccc3ccc12 | Other | C(Cl)Cl | null | 4 | COc1ccc2c(c1)CN(c1ccc(OCCN3CCCCC3)cc1)c1c-2ccc2cc(OC)ccc12>C(Cl)Cl>Oc1ccc2c(c1)CN(c1ccc(OCCN3CCCCC3)cc1)c1c-2ccc2cc(O)ccc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5ac5c62883484e62b790bfad4bc5e3bb | COc1ccc2c(c1)SC(=O)C2.O=Cc1ccccc1O>>COc1ccc2c(c1)SC1c3ccccc3OC(=O)C21 | COC1=CC2=C(CC(=O)S2)C=C1.C(C=1C(O)=CC=CC1)=O>>COC1=CC2=C(C=C1)C1C(OC3=C(C1S2)C=CC=C3)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[S:9][C:18](=[O:19])[CH2:20]2.O=[CH:10][c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[OH:17]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[S:9][CH:10]1[c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[O:17][C:18](=[O:19])[CH:20]21 | COc1ccc2c(c1)SC(=O)C2.O=Cc1ccccc1O | COc1ccc2c(c1)SC1c3ccccc3OC(=O)C21 | null | C(C)N(CC)CC | C(C)O.C(Cl)Cl | Acylation | OtherReaction | e8fbc487563db87775f9ef5b53c3692d363b1a0498769b64bd7c794649742d9d | 7259bf0e4ba555fe66049920a15c643fe90ace826f32b0be86332a42da8e3e0d | O=C1Oc2ccccc2C2Sc3ccccc3C12 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4](-[OH;D1;+0:5]):[c:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-[CH2;D2;+0:9]-[c:10](:[c:11]):[c:12](:[c:13])-[S;H0;D2;+0:14]-1>>[O;D1;H0:7]=[C;H0;D3;+0:8]1-[O;H0;D2;+0:5]-[c:4](:[c:6]):[c:2](:[c:3])-[CH;D3;+0:1]2-[S;H0;D2;+0:14]-[c:12](:[c:13]):[c:10](:[c:11])-[CH;D3;+0:9]-1-2 | 83 | [{"value": 83.0, "product": "COC1=CC2=C(C=C1)C1C(OC3=C(C1S2)C=CC=C3)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.8, "product": "COC1=CC2=C(C=C1)C1C(OC3=C(C1S2)C=CC=C3)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a stirred solution of 6-methoxythianaphthen-2-one (52.6 g, 290 mmol) in a mixture of ethanol (260 mL) and methylene chloride (130 mL) was added triethylamine (2.0 mL, 14.8 mmol) followed by salicylaldehyde (32 mL, 300 mmol) at room temperature. After 1 h, a solid began to precipitate and stirring was continued for 3... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Aromatic alcohol.Carbo-thioester | Ester.Monosulfide | c1ccc2c(c1)CCS2 | c1ccc2c(c1)OCC1c3ccccc3SC21 | c1ccc2c(c1)OCC1c3ccccc3SC21 | HO- | C(C)N(CC)CC.C(C)O.C(Cl)Cl | null | 1 | COc1ccc2c(c1)SC(=O)C2.O=Cc1ccccc1O>C(C)N(CC)CC.C(C)O.C(Cl)Cl>COc1ccc2c(c1)SC1c3ccccc3OC(=O)C21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9870787f9e3f4d56b73d33d54187af4f | COc1ccc2c(c1)CCc1c-2n(-c2ccc(OCCN3CCCCC3)cc2)c(=O)c2cc(OC)ccc12>>COc1ccc2c(c1)CN(c1ccc(OCCN3CCCCC3)cc1)C1=C2CCc2cc(OC)ccc21 | COC=1C=CC2=C(CCC=3C4=CC=C(C=C4C(N(C23)C2=CC=C(C=C2)OCCN2CCCCC2)=O)OC)C1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>COC=1C=CC2=C(CCC=3C4=CC=C(C=C4CN(C23)C2=CC=C(C=C2)OCCN2CCCCC2)OC)C1 | O=[c:9]1[n:10](-[c:11]2[cH:12][cH:13][c:14]([O:15][CH2:16][CH2:17][N:18]3[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]3)[cH:24][cH:25]2)[c:27]2[c:26]([c:37]3[c:30]1[cH:31][c:32]([O:33][CH3:34])[cH:35][cH:36]3)[CH2:28][CH2:29][c:7]1[c:6]-2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8... | COc1ccc2c(c1)CCc1c-2n(-c2ccc(OCCN3CCCCC3)cc2)c(=O)c2cc(OC)ccc12 | COc1ccc2c(c1)CN(c1ccc(OCCN3CCCCC3)cc1)C1=C2CCc2cc(OC)ccc21 | null | null | C1CCOC1 | Reduction | OtherReaction | cb18ab27282d46f4a41097f59a4cd81ab68f1c74c5369f5c346d3507faec4980 | b253d4575341720f8cb1bb1880f1e68453d6628d64a267e66737eafe44470ded | c1ccc2c(c1)CN(c1ccc(OCCN3CCCCC3)cc1)C1=C2CCc2ccccc21 | O=[c;H0;D3;+0:1]1:[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5](:[c:6]):[c;H0;D3;+0:7]2:[c;H0;D3;+0:8](:[n;H0;D3;+0:9]:1-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14])-[c;H0;D3;+0:15]1:[c:16]:[c:17]:[c:18]:[c:19]:[c;H0;D3;+0:20]:1-[CH2;D2;+0:21]-[CH2;D2;+0:22]-2>>[c:12]:[c:11]:[c;H0;D3;+0:10](-[N;H0;D3;+0:9]1-[CH2;D2;+0:1]-[c;H0;... | 72.4 | [{"value": 64.0, "product": "COC=1C=CC2=C(CCC=3C4=CC=C(C=C4CN(C23)C2=CC=C(C=C2)OCCN2CCCCC2)OC)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.4, "product": "COC=1C=CC2=C(CCC=3C4=CC=C(C=C4CN(C23)C2=CC=C(C=C2)OCCN2CCCCC2)OC)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of the product of Example 12 (350 mg, 0.69 mmol) in THF (25 mL) was treated with lithium aluminum hydride (129 mg, 3.4 mmol) inducing a moderate exotherm. The mixture was allowed to return to room temperature and stirred for 2 h, then briefly warmed to reflux, cooled, and quenched with ethyl acetate (50 mL) ... | 10.6084/m9.figshare.5104873.v1 | null | null | Enamine | c1ccc2c(c1)CCc1c3ccccc3cnc12 | c1ccc2c(c1)C[NH]C1=C2CCc2ccccc21 | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)C[NH]C1=C2CCc2ccccc21 | Other | C1CCOC1 | null | 2 | COc1ccc2c(c1)CCc1c-2n(-c2ccc(OCCN3CCCCC3)cc2)c(=O)c2cc(OC)ccc12>C1CCOC1>COc1ccc2c(c1)CN(c1ccc(OCCN3CCCCC3)cc1)C1=C2CCc2cc(OC)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8c93a62461734d1c98f9eb63bc7a7f2a | CN(C)C=O.NNCC(=O)N[C@@H](CC(=O)OCc1ccccc1)C(=O)N[C@@H](Cc1ccccc1)C(=O)OCc1ccccc1.On1nnc2ccccc21>>Nc1cccc(CCC(=O)NCC(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](Cc2ccccc2)C(=O)O)n1 | C(CCl)Cl.N(CC(=O)N[C@@H](CC(OCC1=CC=CC=C1)=O)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)OCC1=CC=CC=C1)N.Cl.C(C)(C)N(CC)C(C)C.CN(C=O)C.C=1C=CC2=C(C1)N=NN2O>>NC1=CC=CC(=N1)CCC(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O | CN(C)[CH:9]=[O:10].c1ccc(C[O:20][C:18]([CH2:17][C@H:16]([NH:15][C:13]([CH2:12][NH:11][NH2:1])=[O:14])[C:21](=[O:22])[NH:23][C@@H:24]([CH2:25][c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[C:32](=[O:33])[O:34]Cc2ccccc2)=[O:19])cc1.O[n:35]1nnc2[c:2]1[cH:3][cH:4][cH:5][cH:6]2>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][CH... | CN(C)C=O.NNCC(=O)N[C@@H](CC(=O)OCc1ccccc1)C(=O)N[C@@H](Cc1ccccc1)C(=O)OCc1ccccc1.On1nnc2ccccc21 | Nc1cccc(CCC(=O)NCC(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](Cc2ccccc2)C(=O)O)n1 | null | [Pd] | C(C)O | C-C Coupling | OtherReaction | aa57fac1c9d9cb97858634258eb1a7fe21fcb884d41c6750757f83562faf70e2 | e666beabd03b26d2855b8e8d5725ec0e57b2ce795c53b22bd9e1f0737e7ba1bc | O=C(CCc1ccccn1)NCC(=O)NCC(=O)NCCc1ccccc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].O-[n;H0;D3;+0:3]1:n:n:c2:[cH;D2;+0:4]:[c:5]:[c:6]:[c:7]:[c;H0;D3;+0:8]:1:2.[NH2;D1;+0:9]-[NH;D2;+0:10]-[C:11]-[C:12](=[O;D1;H0:13])-[#7:14]-[C:15](-[C:16]-[C:17](=[O;D1;H0:18])-[O;H0;D2;+0:19]-C-c1:c:c:c:c:c:1)-[C:20](=[O;D1;H0:21])-[#7:22]-[C:23]-[C:24](=[O;D1;H0:25])-[O;H0;D2;+0:26]-C... | 10 | [{"value": 10.0, "product": "NC1=CC=CC(=N1)CCC(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 18 | HOUR | 3-(2-[6-Aminopyridyl])-propionic acid (63 mg, 0.28 mmol), HOBT (50 mg, 0.37 mmol), HCl.H2N-Gly-Asp(OBn)-Phe-OBn (155 mg, 0.28 mmol) and diisopropylethylamine were combined in 7 ml of dry dimethylformamide. The reaction mixture was cooled to 0° C. EDC (68 mg, 0.35 mmol) was added in one portion, the reaction mixture all... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester.Ester.Tertiary amide | Carboxylic acid.Carboxylic acid.Secondary amide.Primary amine | c1ccccc1.c1ccccc1.c1ccc2[nH]nnc2c1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HO- | [Pd].C(C)O | 0 | 18 | CN(C)C=O.NNCC(=O)N[C@@H](CC(=O)OCc1ccccc1)C(=O)N[C@@H](Cc1ccccc1)C(=O)OCc1ccccc1.On1nnc2ccccc21>[Pd].C(C)O>Nc1cccc(CCC(=O)NCC(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](Cc2ccccc2)C(=O)O)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-37d4e94f18a64572955158f797a738e8 | COC(CN=C=S)OC.N>>COC(CNC(N)=S)OC | N.COC(CN=C=S)OC>>COC(CNC(=S)N)OC | [CH3:1][O:2][CH:3]([CH2:4][N:5]=[C:6]=[S:8])[O:9][CH3:10].[NH3:7]>>[CH3:1][O:2][CH:3]([CH2:4][NH:5][C:6]([NH2:7])=[S:8])[O:9][CH3:10] | COC(CN=C=S)OC.N | COC(CNC(N)=S)OC | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 9ea44f258f40d07ea72818ac0d167217e6d11d32357aad8e81d4f079b5cbad85 | 8a79caa9356d3b30a3b61a9504f2b151cec34b3b4ac7afcdd36f0060d08e7701 | null | [C:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[S;D1;H0:5].[NH3;D0;+0:6]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](-[NH2;D1;+0:6])=[S;D1;H0:5] | null | [] | null | null | null | null | Methanol (200 mL) was saturated with ammonia and stirred with isothiocyanatoacetaldehyde dimethyl acetal (5.0 g) for 2 h. The mixture was concentrated and the residue was chromatographed (silica gel, 5% methanol/dichloromethane) to give the title compound.
Conditions: See reaction.notes.procedure_details.
Workup: The m... | 10.6084/m9.figshare.5104873.v1 | null | Isothiocyanate | Thiourea | null | null | null | null | CO | null | null | COC(CN=C=S)OC.N>CO>COC(CNC(N)=S)OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ccae603003f14fca9668b5a8da6d0d4d | CNCC(=O)OCc1ccccc1.O=C1CCC(=O)O1>>CN(CC(=O)OCc1ccccc1)C(=O)CCC(=O)O | C(C1=CC=CC=C1)OC(CNC)=O.C1(CCC(=O)O1)=O>>C(C1=CC=CC=C1)OC(CN(C)C(CCC(=O)O)=O)=O | [CH3:1][NH:2][CH2:3][C:4](=[O:5])[O:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1.[C:14]1(=[O:15])[CH2:16][CH2:17][C:18](=[O:19])[O:20]1>>[CH3:1][N:2]([CH2:3][C:4](=[O:5])[O:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[C:14](=[O:15])[CH2:16][CH2:17][C:18](=[O:19])[OH:20] | CNCC(=O)OCc1ccccc1.O=C1CCC(=O)O1 | CN(CC(=O)OCc1ccccc1)C(=O)CCC(=O)O | null | null | C1(=CC=CC=C1)C | Protection | OtherReaction | 75be88e6b83c45fccbc410b13860a053f9023d8701f41828baea71b5452e7745 | 95d83cdac3a1d5509861e8b6462ab8c8218ba78b52ab99766013cb9b1af0d20d | c1ccccc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]-[NH;D2;+0:6]-[C;D1;H3:7].[O;D1;H0:8]=[C;H0;D3;+0:9]1-[C:10]-[C:11]-[C:12](=[O;D1;H0:13])-[O;H0;D2;+0:14]-1>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[C;H0;D3;+0:9](=[O;D1;H0:8])-[C:10]-[C:11]-[C:12](=[O;D1;H0:13])-[OH;D1;+0:14] | 86.3 | [{"value": 67.5, "product": "C(C1=CC=CC=C1)OC(CN(C)C(CCC(=O)O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.3, "product": "C(C1=CC=CC=C1)OC(CN(C)C(CCC(=O)O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of sarcosine benzyl ester (3.0 g, 30.7 mmol) and succinic anhydride (5.5 g, 30.7 mmol) in toluene (75 mL) was heated to reflux for 3 h, cooled, filtered, and the filtrate was concentrated. The residue was taken up in 5% aqueous sodium carbonate and extracted with ethyl acetate. The aqueous phase was adjusted ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary amine | Carboxylic acid.Tertiary amide | C1CCOC1 | null | c1ccccc1 | null | C1(=CC=CC=C1)C | null | null | CNCC(=O)OCc1ccccc1.O=C1CCC(=O)O1>C1(=CC=CC=C1)C>CN(CC(=O)OCc1ccccc1)C(=O)CCC(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bcef87ed7a7043ef86ee001ff10769ae | CC(C)(C)OC(=O)NCC(=O)O.N[C@@H](CC(=O)OC1CCCCC1)C(=O)O>>CC(C)(C)OC(=O)NCC(=O)N[C@@H](CC(=O)OC1CCCCC1)C(=O)O | N(CC(=O)O)C(=O)OC(C)(C)C.C(C)N=C=NCCCN(C)C.N[C@@H](CC(OC1CCCCC1)=O)C(=O)O.OC1[C@@H](O)[C@@H](O)[C@H](OCC2=CC=C(C)C=C2)[C@H](O1)CO.CN(C)C=O.ON1N=NC2=C1C=CC=C2>>N(CC(=O)N[C@@H](CC(OC1CCCCC1)=O)C(=O)O)C(=O)OC(C)(C)C.OC1[C@@H](O)[C@@H](O)[C@H](OCC2=CC=C(C)C=C2)[C@H](O1)CO | O[C:10]([CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])=[O:11].[NH2:12][C@@H:13]([CH2:14][C:15](=[O:16])[O:17][CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1)[C:24](=[O:25])[OH:26]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][C:10](=[O:11])[NH:12][C@@H:13]([CH2:14][C:15](=[O:16])[O:17... | CC(C)(C)OC(=O)NCC(=O)O.N[C@@H](CC(=O)OC1CCCCC1)C(=O)O | CC(C)(C)OC(=O)NCC(=O)N[C@@H](CC(=O)OC1CCCCC1)C(=O)O | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | C1CCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11].[#8:12]-[C:13](=[O;D1;H0:14])-[C:15]-[C:16](-[NH2;D1;+0:17])-[C:18](=[O;D1;H0:19])-[O;D1;H1:20]>>[#8:12]-[C:13](=[O;D1;H0:14])-[C:15]-[C:16](-[NH;D2;+0:17]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:... | 89.2 | [{"value": 89.2, "product": "N(CC(=O)N[C@@H](CC(OC1CCCCC1)=O)C(=O)O)C(=O)OC(C)(C)C.OC1[C@@H](O)[C@@H](O)[C@H](OCC2=CC=C(C)C=C2)[C@H](O1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a cold solution of Asp(O-cHex)-Man(4-MBzl) (46.7 g, 86.4 mmol) in DMF (100 mL) diisopropylethylamine (15 mL, 86.1 mmol) was added. N-Hydroxybezotriazole (14.0 g, 104 mmol) was added followed by Boc-Gly (16.6 g, 94.8 mmol). The reaction mixture was stirred in the cold for a few minutes, and N-ethyl-N'(dimethylaminopr... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CCCCC1 | HO- | null | null | null | CC(C)(C)OC(=O)NCC(=O)O.N[C@@H](CC(=O)OC1CCCCC1)C(=O)O>>CC(C)(C)OC(=O)NCC(=O)N[C@@H](CC(=O)OC1CCCCC1)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-49f6270560624c5e98c775fdae86e129 | Nc1ccc(-c2ccc(N)c(N)c2)cc1N.O=C(O)/C=C/C=C/C(=O)O>>C#C.C#C.c1ccc2[nH]cnc2c1.c1ccc2[nH]cnc2c1 | NC=1C=C(C=CC1N)C1=CC(=C(N)C=C1)N.C(\C=C\C=C\C(=O)O)(=O)O>>C#C.C#C.N1=CNC2=C1C=CC=C2.N2=CNC1=C2C=CC=C1 | [c:5]1(-[c:14]2[cH:15][cH:16][c:17]([NH2:18])[c:21]([NH2:20])[cH:22]2)[cH:6][cH:7][c:8]([NH2:9])[c:12]([NH2:11])[cH:13]1.O=[C:10](O)/[CH:4]=[CH:2]/[CH:1]=[CH:3]/[C:19](=O)O>>[CH:1]#[CH:2].[CH:3]#[CH:4].[cH:5]1[cH:6][cH:7][c:8]2[nH:9][cH:10][n:11][c:12]2[cH:13]1.[cH:14]1[cH:15][cH:16][c:17]2[nH:18][cH:19][n:20][c:21]2[c... | Nc1ccc(-c2ccc(N)c(N)c2)cc1N.O=C(O)/C=C/C=C/C(=O)O | C#C.C#C.c1ccc2[nH]cnc2c1.c1ccc2[nH]cnc2c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 64aee3e13525c08a2cbef9993db4cf018b917c6ee7971e6ae287c4630fdee485 | ad0a0f5871c13b069ca26b80b625bdedff486cbebfe95426d60993b066e77137 | c1ccc2[nH]cnc2c1.c1ccc2[nH]cnc2c1 | O-[C;H0;D3;+0:1](=O)/[CH;D2;+0:2]=[CH;D2;+0:3]/[CH;D2;+0:4]=[CH;D2;+0:5]/[C;H0;D3;+0:6](-O)=O.[NH2;D1;+0:7]-[c:8]1:[c:9]:[c;H0;D3;+0:10](-[c;H0;D3;+0:11]2:[c:12]:[c:13]:[c:14](-[NH2;D1;+0:15]):[c:16](-[NH2;D1;+0:17]):[c:18]:2):[c:19]:[c:20]:[c:21]:1-[NH2;D1;+0:22]>>[CH;D1;+0:4]#[CH;D1;+0:3].[CH;D1;+0:5]#[CH;D1;+0:2].[c... | null | [] | null | null | null | null | 3,3'-Diaminobenzidine (1.508 g, 7.04 mmol) was dehydrochlorinated with 83.3 wt % deaerated PPA in accordance with the procedure enumerated in Example 1. The product of this dehydrochlorination was reacted with trans,trans-muconic acid (1.0 g, 7.04 mmol) in accordance with the procedure of Example 1. This polymerization... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Primary amine.Primary amine.Primary amine.Primary amine.Conjugated diene | Alkyne.Alkyne | c1ccccc1.c1ccccc1 | c1ccc2[nH]cnc2c1.c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1.c1ccc2[nH]cnc2c1 | HO- | null | null | null | Nc1ccc(-c2ccc(N)c(N)c2)cc1N.O=C(O)/C=C/C=C/C(=O)O>>C#C.C#C.c1ccc2[nH]cnc2c1.c1ccc2[nH]cnc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b158250efe4c40eebdb1b21930a1a3f4 | CCO.CCOC(=O)OCC.Cc1ccccc1.Cc1ccccc1.O>>O=c1cc(O)c2ccc(OCc3ccccc3)cc2o1 | C(C)O.C1(=CC=CC=C1)C.C(OCC)(OCC)=O.[H-].[Na+].C1(=CC=CC=C1)C.O>>C(C1=CC=CC=C1)OC1=CC=C2C(=CC(OC2=C1)=O)O | C[CH2:11][OH:10].CCO[C:2](=[O:1])[O:20]C[CH3:3].[CH3:4][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.C[c:9]1[cH:8][cH:7][cH:6][cH:19][cH:18]1.[OH2:5]>>[O:1]=[c:2]1[cH:3][c:4]([OH:5])[c:6]2[cH:7][cH:8][c:9]([O:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][c:19]2[o:20]1 | CCO.CCOC(=O)OCC.Cc1ccccc1.Cc1ccccc1.O | O=c1cc(O)c2ccc(OCc3ccccc3)cc2o1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | be35ef74b40b7d957ec8047d8dc673b1caff4483920f29c19cc5b15deebfce29 | dbd17518751cc08c5e0fc4e9f0128fc615bc09bcdbd2410dc38bce2febf6d1b1 | O=c1ccc2ccc(OCc3ccccc3)cc2o1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:3]-C-[CH3;D1;+0:4].C-[CH2;D2;+0:5]-[OH;D1;+0:6].C-[c;H0;D3;+0:7]1:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:[c:11]:[c:12]:1.[CH3;D1;+0:13]-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18].[OH2;D0;+0:19]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[cH;D2;+0:4]:[c;H0;D3;+0:13](-[OH;D1;+0:19]):[c;H0;D3... | 84 | [{"value": 84.0, "product": "C(C1=CC=CC=C1)OC1=CC=C2C(=CC(OC2=C1)=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Benzyloxy-2-hydroxy-acetophenone (20 g, 0.0825 mol), prepared in accordance with Example 4, was dissolved in 150 mL of toluene. To this solution was added diethyl carbonate (25.3 g, 0.21 mol) and the entire contents taken in a beaker was heated while stirring to dissolve the starting material. This solution was then ... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Primary alcohol | Ether.Aromatic alcohol | c1ccccc1.c1ccccc1 | c1ccc2cccoc2c1.c1ccccc1 | c1ccc2cccoc2c1.c1ccccc1 | HO- | null | null | null | CCO.CCOC(=O)OCC.Cc1ccccc1.Cc1ccccc1.O>>O=c1cc(O)c2ccc(OCc3ccccc3)cc2o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fc45e6d9775a4f599ceedc6dcd5fe8bc | O=c1cc(O)c2ccc(OCc3ccccc3)cc2o1>>O=c1cc(O)c2ccc(O)cc2o1 | C(C1=CC=CC=C1)OC1=CC=C2C(=CC(OC2=C1)=O)O>>OC1=CC(OC2=CC(=CC=C12)O)=O | c1ccc(C[O:10][c:9]2[cH:8][cH:7][c:6]3[c:4]([OH:5])[cH:3][c:2](=[O:1])[o:13][c:12]3[cH:11]2)cc1>>[O:1]=[c:2]1[cH:3][c:4]([OH:5])[c:6]2[cH:7][cH:8][c:9]([OH:10])[cH:11][c:12]2[o:13]1 | O=c1cc(O)c2ccc(OCc3ccccc3)cc2o1 | O=c1cc(O)c2ccc(O)cc2o1 | null | [Pd] | CO | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=c1ccc2ccccc2o1 | [#8;a:1]:[c:2]:[c:3]:[c:4](-[O;H0;D2;+0:5]-C-c1:c:c:c:c:c:1):[c:6]>>[#8;a:1]:[c:2]:[c:3]:[c:4](-[OH;D1;+0:5]):[c:6] | 90 | [{"value": 90.0, "product": "OC1=CC(OC2=CC(=CC=C12)O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A 300 cc autoclave was charged with 7-benzyloxy-4-hydroxycoumarin (3 g, 3.7 mmol), prepared in accordance with Example 5, 5% Pd on carbon (0.18 g) and 85 mL of methanol and the autoclave was purged with N2. The autoclave was pressurized with H2 to a pressure of about 100 psi and maintained at that pressure. The exother... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccc2cccoc2c1 | Other | [Pd].CO | null | null | O=c1cc(O)c2ccc(OCc3ccccc3)cc2o1>[Pd].CO>O=c1cc(O)c2ccc(O)cc2o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-eafe799634bf413884245083d524cea5 | Cc1ccc(S(=O)(=O)N=[N+]=[N-])cc1.O=c1cc(O)c2ccc(OCc3ccccc3)cc2o1>>[N-]=[N+]=C1C(=O)Oc2cc(OCc3ccccc3)ccc2C1=O | C1(=CC=C(C=C1)S(=O)(=O)N=[N+]=[N-])C.C(C1=CC=CC=C1)OC1=CC=C2C(=CC(OC2=C1)=O)O.C(C)N(CC)CC>>[N+](=[N-])=C1C(OC2=CC(=CC=C2C1=O)OCC1=CC=CC=C1)=O | Cc1ccc(S(=O)(=O)[N:1]=[N+:2]=[N-])cc1.[cH:3]1[c:4](=[O:5])[o:6][c:7]2[cH:8][c:9]([O:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][cH:19][c:20]2[c:21]1[OH:22]>>[N-:1]=[N+:2]=[C:3]1[C:4](=[O:5])[O:6][c:7]2[cH:8][c:9]([O:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][cH:19][c:20]2[C:21]1=[... | Cc1ccc(S(=O)(=O)N=[N+]=[N-])cc1.O=c1cc(O)c2ccc(OCc3ccccc3)cc2o1 | [N-]=[N+]=C1C(=O)Oc2cc(OCc3ccccc3)ccc2C1=O | null | null | C1CCOC1 | Acylation | OtherReaction | a588281ee0712866d01012f4c8cf674cc1e86d876933bcbee61aed4605b28980 | 16c5bfe4e75246e5d41e0c1283cd592a9e824171ae59abf49dae1b6957964ef9 | [N+]=C1C(=O)Oc2cc(OCc3ccccc3)ccc2C1=O | C-c1:c:c:c(-S(=O)(=O)-[N;H0;D2;+0:1]=[N+;H0;D2:2]=[N-]):c:c:1.[O;D1;H0:3]=[c;H0;D3;+0:4]1:[cH;D2;+0:5]:[c;H0;D3;+0:6](-[OH;D1;+0:7]):[c:8](:[c:9]):[c:10](:[c:11]):[o;H0;D2;+0:12]:1>>[N-;H0;D1:1]=[N+;H0;D2:2]=[C;H0;D3;+0:5]1-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[c:8](:[c:9]):[c:10](:[c:11])-[O;H0;D2;+0:12]-[C;H0;D3;+0:4]-1=[... | 90 | [{"value": 90.0, "product": "[N+](=[N-])=C1C(OC2=CC(=CC=C2C1=O)OCC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A solution of 7-benzyloxy -4-hydroxy coumarin (2.5 g, 9.3 mmol; prepared in accordance with Example 5) in anhydrous THF (40 mL) was mixed with triethylamine (0.9 g, 9 mmol) taken in a 100 mL 3-neck round-bottom flask under an atmosphere of N2. A solution of p-toluenesulfonyl azide (2.8 g, 14 mmol) in dry THF (20 mL) wa... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Azide.Aromatic alcohol | Ketone.Ester.Diazo | c1ccccc1.c1ccc2cccoc2c1 | c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2.c1ccccc1 | TsOH.HO- | C1CCOC1 | null | 3 | Cc1ccc(S(=O)(=O)N=[N+]=[N-])cc1.O=c1cc(O)c2ccc(OCc3ccccc3)cc2o1>C1CCOC1>[N-]=[N+]=C1C(=O)Oc2cc(OCc3ccccc3)ccc2C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d813d0f041e246f1a6849017f99fae8a | CCO.CCOC(=O)OCC.Cc1ccccc1.Cc1ccccc1.O>>O=c1cc(O)c2ccc(OCc3ccccc3)cc2o1 | C(C)O.C1(=CC=CC=C1)C.C(OCC)(OCC)=O.[H-].[Na+].C1(=CC=CC=C1)C.O>>C(C1=CC=CC=C1)OC1=CC=C2C(=CC(OC2=C1)=O)O | C[CH2:11][OH:10].CCO[C:2](=[O:1])[O:20]C[CH3:3].[CH3:4][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.C[c:9]1[cH:8][cH:7][cH:6][cH:19][cH:18]1.[OH2:5]>>[O:1]=[c:2]1[cH:3][c:4]([OH:5])[c:6]2[cH:7][cH:8][c:9]([O:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][c:19]2[o:20]1 | CCO.CCOC(=O)OCC.Cc1ccccc1.Cc1ccccc1.O | O=c1cc(O)c2ccc(OCc3ccccc3)cc2o1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | be35ef74b40b7d957ec8047d8dc673b1caff4483920f29c19cc5b15deebfce29 | dbd17518751cc08c5e0fc4e9f0128fc615bc09bcdbd2410dc38bce2febf6d1b1 | O=c1ccc2ccc(OCc3ccccc3)cc2o1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:3]-C-[CH3;D1;+0:4].C-[CH2;D2;+0:5]-[OH;D1;+0:6].C-[c;H0;D3;+0:7]1:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:[c:11]:[c:12]:1.[CH3;D1;+0:13]-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18].[OH2;D0;+0:19]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[cH;D2;+0:4]:[c;H0;D3;+0:13](-[OH;D1;+0:19]):[c;H0;D3... | 84 | [{"value": 84.0, "product": "C(C1=CC=CC=C1)OC1=CC=C2C(=CC(OC2=C1)=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Benzyloxy-2-hydroxy-acetophenone (20 g, 0.0825 mol), prepared in accordance with Example 4, was dissolved in 150 mL of toluene. To this solution was added diethyl carbonate (25.3 g, 0.21 mol) and the entire contents taken in a beaker was heated while stirring to dissolve the starting material. This solution was then ... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Primary alcohol | Ether.Aromatic alcohol | c1ccccc1.c1ccccc1 | c1ccc2cccoc2c1.c1ccccc1 | c1ccc2cccoc2c1.c1ccccc1 | HO- | null | null | null | CCO.CCOC(=O)OCC.Cc1ccccc1.Cc1ccccc1.O>>O=c1cc(O)c2ccc(OCc3ccccc3)cc2o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0732293e181346eba1ff8d891ce02cf4 | O=c1cc(O)c2ccc(OCc3ccccc3)cc2o1>>O=c1cc(O)c2ccc(O)cc2o1 | C(C1=CC=CC=C1)OC1=CC=C2C(=CC(OC2=C1)=O)O>>OC1=CC(OC2=CC(=CC=C12)O)=O | c1ccc(C[O:10][c:9]2[cH:8][cH:7][c:6]3[c:4]([OH:5])[cH:3][c:2](=[O:1])[o:13][c:12]3[cH:11]2)cc1>>[O:1]=[c:2]1[cH:3][c:4]([OH:5])[c:6]2[cH:7][cH:8][c:9]([OH:10])[cH:11][c:12]2[o:13]1 | O=c1cc(O)c2ccc(OCc3ccccc3)cc2o1 | O=c1cc(O)c2ccc(O)cc2o1 | null | [Pd] | CO | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=c1ccc2ccccc2o1 | [#8;a:1]:[c:2]:[c:3]:[c:4](-[O;H0;D2;+0:5]-C-c1:c:c:c:c:c:1):[c:6]>>[#8;a:1]:[c:2]:[c:3]:[c:4](-[OH;D1;+0:5]):[c:6] | 90 | [{"value": 90.0, "product": "OC1=CC(OC2=CC(=CC=C12)O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A 300 cc autoclave was charged with 7-benzyloxy-4-hydroxycoumarin (3 g, 3.7 mmol), prepared in accordance with Example 5, 5% Pd on carbon (0.18 g) and 85 mL of methanol and the autoclave was purged with N2. The autoclave was pressurized with H2 to a pressure of about 100 psi and maintained at that pressure. The exother... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccc2cccoc2c1 | Other | [Pd].CO | null | null | O=c1cc(O)c2ccc(OCc3ccccc3)cc2o1>[Pd].CO>O=c1cc(O)c2ccc(O)cc2o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2be13a8581c44d4eb5c7cef82a7c8e6c | Cc1ccc(S(=O)(=O)N=[N+]=[N-])cc1.O=c1cc(O)c2ccc(OCc3ccccc3)cc2o1>>[N-]=[N+]=C1C(=O)Oc2cc(OCc3ccccc3)ccc2C1=O | C1(=CC=C(C=C1)S(=O)(=O)N=[N+]=[N-])C.C(C1=CC=CC=C1)OC1=CC=C2C(=CC(OC2=C1)=O)O.C(C)N(CC)CC>>[N+](=[N-])=C1C(OC2=CC(=CC=C2C1=O)OCC1=CC=CC=C1)=O | Cc1ccc(S(=O)(=O)[N:1]=[N+:2]=[N-])cc1.[cH:3]1[c:4](=[O:5])[o:6][c:7]2[cH:8][c:9]([O:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][cH:19][c:20]2[c:21]1[OH:22]>>[N-:1]=[N+:2]=[C:3]1[C:4](=[O:5])[O:6][c:7]2[cH:8][c:9]([O:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][cH:19][c:20]2[C:21]1=[... | Cc1ccc(S(=O)(=O)N=[N+]=[N-])cc1.O=c1cc(O)c2ccc(OCc3ccccc3)cc2o1 | [N-]=[N+]=C1C(=O)Oc2cc(OCc3ccccc3)ccc2C1=O | null | null | C1CCOC1 | Acylation | OtherReaction | a588281ee0712866d01012f4c8cf674cc1e86d876933bcbee61aed4605b28980 | 16c5bfe4e75246e5d41e0c1283cd592a9e824171ae59abf49dae1b6957964ef9 | [N+]=C1C(=O)Oc2cc(OCc3ccccc3)ccc2C1=O | C-c1:c:c:c(-S(=O)(=O)-[N;H0;D2;+0:1]=[N+;H0;D2:2]=[N-]):c:c:1.[O;D1;H0:3]=[c;H0;D3;+0:4]1:[cH;D2;+0:5]:[c;H0;D3;+0:6](-[OH;D1;+0:7]):[c:8](:[c:9]):[c:10](:[c:11]):[o;H0;D2;+0:12]:1>>[N-;H0;D1:1]=[N+;H0;D2:2]=[C;H0;D3;+0:5]1-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[c:8](:[c:9]):[c:10](:[c:11])-[O;H0;D2;+0:12]-[C;H0;D3;+0:4]-1=[... | 90 | [{"value": 90.0, "product": "[N+](=[N-])=C1C(OC2=CC(=CC=C2C1=O)OCC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A solution of7-benzyloxy-4-hydroxy coumarin (2.5 g, 9.3 mmol; prepared in accordance with Example 5) in anhydrous THF (40 mL) was mixed with triethylamine (0.9 g, 9 mmol) taken in a 100 mL 3-neck round-bottom flask under an atmosphere of N2. A solution of p-toluenesulfonyl azide (2.8 g, 14 mmol) in dry THF (20 mL) was ... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Azide.Aromatic alcohol | Ketone.Ester.Diazo | c1ccccc1.c1ccc2cccoc2c1 | c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2.c1ccccc1 | TsOH.HO- | C1CCOC1 | null | 3 | Cc1ccc(S(=O)(=O)N=[N+]=[N-])cc1.O=c1cc(O)c2ccc(OCc3ccccc3)cc2o1>C1CCOC1>[N-]=[N+]=C1C(=O)Oc2cc(OCc3ccccc3)ccc2C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-61e90dfc436e46c68b3d763ba8118cbb | CC(=O)OC(C)=O.Nc1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)n1>>CC(=O)Nc1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)n1 | [C@@H]1(C[C@H](O)[C@@H](CO)O1)N1C(=O)N=C(N)C=C1.C(C)(=O)OC(C)=O>>C(C)(=O)NC1=NC(N([C@H]2C[C@H](O)[C@@H](CO)O2)C=C1)=O | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][n:8]([C@H:9]2[CH2:10][C@H:11]([OH:12])[C@@H:13]([CH2:14][OH:15])[O:16]2)[c:17](=[O:18])[n:19]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][n:8]([C@H:9]2[CH2:10][C@H:11]([OH:12])[C@@H:13]([CH2:14][OH:15])[O:16]2)[c:17](=[O:18])[n:19]1 | CC(=O)OC(C)=O.Nc1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)n1 | CC(=O)Nc1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)n1 | null | null | CN(C=O)C | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=c1ncccn1[C@H]1CCCO1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1 | 98.2 | [{"value": 98.0, "product": "C(C)(=O)NC1=NC(N([C@H]2C[C@H](O)[C@@H](CO)O2)C=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.2, "product": "C(C)(=O)NC1=NC(N([C@H]2C[C@H](O)[C@@H](CO)O2)C=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | To 61.29 g (270 mmol) of the material of Example I dissolved in 1300 ml of anhydrous N,N-dimethylformamide ("DMF") (Aldrich; Cat. No. 22, 70506), was added 28 ml (296 mmol) of acetic anhydride (Aldrich; Cat. No. 11,004-3), and the resulting mixture was stirred at room temperature for 20 hrs. DMF was removed under reduc... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1cncnc1.C1CCOC1 | HO- | CN(C=O)C | null | 20 | CC(=O)OC(C)=O.Nc1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)n1>CN(C=O)C>CC(=O)Nc1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3780dab8e7fc4abdb18faae656691afb | OC[C@@H](O)[C@@H](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@@H](O)CO>>OC[C@H]1O[C@@H](O[C@@H]2[C@@H](CO)O[C@](O)(CO)[C@H]2O)[C@H](O)[C@@H](O)[C@H]1O | C([C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@H]([C@@H](CO)O)[C@@H]([C@H](CO)O)O)O)O)O)O.O.C([C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@H]([C@@H](CO)O)[C@@H]([C@H](CO)O)O)O)O)O)O.O.O>>C([C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@@]([C@H]2O)(CO)O)CO)O)O)O)O | [OH:1][CH2:2][C@H:3]1[O:4][C@@H:5]([O:6][C@H:7]([C@@H:8]([CH2:9][OH:10])[OH:11])[C@@H:16]([C@@H:12]([OH:13])[CH2:14][OH:15])[OH:17])[C@H:18]([OH:19])[C@@H:20]([OH:21])[C@H:22]1[OH:23]>>[OH:1][CH2:2][C@H:3]1[O:4][C@@H:5]([O:6][C@@H:7]2[C@@H:8]([CH2:9][OH:10])[O:11][C@:12]([OH:13])([CH2:14][OH:15])[C@H:16]2[OH:17])[C@H:1... | OC[C@@H](O)[C@@H](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@@H](O)CO | OC[C@H]1O[C@@H](O[C@@H]2[C@@H](CO)O[C@](O)(CO)[C@H]2O)[C@H](O)[C@@H](O)[C@H]1O | null | null | null | Oxidation | OtherReaction | 278cf296da9870749f18ed71f2bfd7f7f5f66e19da4bee88ccbf5f43b75dda7b | 5da3fb1ebb4c17ae961f305629feaf8cfc0c08c33829d24f3e8bbd94478beb9a | C1CC[C@H](O[C@H]2CCOC2)OC1 | [C:1]-[C:2](-[OH;D1;+0:3])-[C:4]-[C:5](-[O;D1;H1:6])-[C@@H;D3;+0:7](-[O;D1;H1:8])-[C:9]-[O;D1;H1:10]>>[C:1]-[C:2]1-[C:4]-[C:5](-[O;D1;H1:6])-[C@@;H0;D4;+0:7](-[O;D1;H1:8])(-[C:9]-[O;D1;H1:10])-[O;H0;D2;+0:3]-1 | null | [] | null | null | null | null | Examples XII-XXVII elucidate the conditions at which lactitol monohydrate and lactitol dihydrate, respectively, may be obtained from aqueous solutions of lactitol. In each instance 200 g lactitol dihydrate was used as the starting material which wasd dissolved in an amount of water varying from 40 g to 50 g at 100° C. ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Secondary alcohol | Ether | null | C1CCOC1 | C1CCOCC1.C1CCOC1 | null | null | null | null | OC[C@@H](O)[C@@H](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@@H](O)CO>>OC[C@H]1O[C@@H](O[C@@H]2[C@@H](CO)O[C@](O)(CO)[C@H]2O)[C@H](O)[C@@H](O)[C@H]1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-19ef8b5233de4220a1842b9d3ce2334f | OC[C@@H](O)[C@@H](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@@H](O)CO>>OC[C@@H](O)[C@@H](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@@H](O)CO | C([C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@@]([C@H]2O)(CO)O)CO)O)O)O)O.C([C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@@]([C@H]2O)(CO)O)CO)O)O)O)O.C([C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@H]([C@@H](CO)O)[C@@H]([C@H](CO)O)O)O)O)O)O.O.O>>C([C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@H]([C@@H](CO)O)[... | [OH:2][CH2:3][C@@H:4]([OH:5])[C@@H:6]([O:7][C@@H:8]1[O:9][C@H:10]([CH2:11][OH:12])[C@H:13]([OH:14])[C@H:15]([OH:16])[C@H:17]1[OH:18])[C@H:19]([OH:20])[C@@H:21]([OH:22])[CH2:23][OH:24]>>[OH:2][CH2:3][C@@H:4]([OH:5])[C@@H:6]([O:7][C@@H:8]1[O:9][C@H:10]([CH2:11][OH:12])[C@H:13]([OH:14])[C@H:15]([OH:16])[C@H:17]1[OH:18])[C... | OC[C@@H](O)[C@@H](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@@H](O)CO | OC[C@@H](O)[C@@H](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@@H](O)CO | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | C1CCOCC1 | null | 4.9 | [{"value": 4.9, "product": "C([C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@H]([C@@H](CO)O)[C@@H]([C@H](CO)O)O)O)O)O)O.O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 950 g lactitol dihydrate (860 g anhydric lactitol) were dissolved in 125 g water at 100° C. Upon cooling to 50° C. the 80 percent by weight lactitol solution was seeded with 9.5 g ground dihydrate (1 percent by weight based on the lactitol dissolves). After crystallization for 48 hours at 45° C. the crystals formed wer... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1CCOCC1 | null | O | null | null | OC[C@@H](O)[C@@H](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@@H](O)CO>O>OC[C@@H](O)[C@@H](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@@H](O)CO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3d49ae6f297d47999ae3e523cd23084d | Cc1cccc(C)c1.Clc1nc(Cl)nc(Cl)n1>>Cc1ccc(-c2nc(Cl)nc(-c3ccc(C)cc3C)n2)c(C)c1 | N1=C(Cl)N=C(Cl)N=C1Cl.C1(=CC(=CC=C1)C)C>>ClC1=NC(=NC(=N1)C1=C(C=C(C=C1)C)C)C1=C(C=C(C=C1)C)C | [CH3:1][c:2]1[cH:3][cH:4][cH:23][c:18]([CH3:16])[cH:17]1.Cl[c:5]1[n:7][c:15]([Cl:9])[n:20][c:22](Cl)[n:10]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][c:8]([Cl:9])[n:10][c:11](-[c:12]3[cH:13][cH:14][c:15]([CH3:16])[cH:17][c:18]3[CH3:19])[n:20]2)[c:21]([CH3:22])[cH:23]1 | Cc1cccc(C)c1.Clc1nc(Cl)nc(Cl)n1 | Cc1ccc(-c2nc(Cl)nc(-c3ccc(C)cc3C)n2)c(C)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | d95917990c8fa34e930db780b5436b0e53bbf37db4f64a5de5e7ed86f3153274 | 61b0a5599977a22af270e7bf51ae98dbf8841255d4777bc8dbf1a0b3a43dd3ed | c1ccc(-c2ncnc(-c3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-Cl):[n;H0;D2;+0:4]:[c;H0;D3;+0:5](-[Cl;H0;D1;+0:6]):[n;H0;D2;+0:7]:1.[C;D1;H3:8]-[c;H0;D3;+0:9]1:[c:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[c;H0;D3;+0:13](-[CH3;D1;+0:14]):[cH;D2;+0:15]:1>>[C;D1;H3:16]-[c;H0;D3;+0:13]1:[cH;D2;+0:15]:[c;H0;D3;+0:5](-[CH3;D1;+0:14]):[c:17]:[c:18... | null | [] | null | null | null | null | The reaction of cyanuric chloride with 1,3-xylene under Friedel-Crafts conditions to give 2-chloro-4,6-bis(2,4-dimethylphenyl)-s-triazine is known, e.g. from DE-A-1 169 947 and Helv. Chim. Acta 55, 1589 (1972). However, the product can also be obtained using an appropriate Grignard reagent, such as described in Helv. C... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide | Aromatic halide | c1ccccc1.c1ncncn1 | c1ccccc1.c1ncncn1.c1ccccc1 | c1ccccc1.c1ncncn1.c1ccccc1 | null | null | null | null | Cc1cccc(C)c1.Clc1nc(Cl)nc(Cl)n1>>Cc1ccc(-c2nc(Cl)nc(-c3ccc(C)cc3C)n2)c(C)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a23a2974ba3941e79b71f0f690cd1e1b | O=C(O)c1ccc(I)cc1>>COC(=O)c1ccc(I)cc1 | [N+](=[N-])=C.IC1=CC=C(C(=O)O)C=C1.CCOCC>>COC(C1=CC=C(C=C1)I)=O | [OH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([I:9])[cH:10][cH:11]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([I:9])[cH:10][cH:11]1 | O=C(O)c1ccc(I)cc1 | COC(=O)c1ccc(I)cc1 | null | null | O1CCCC1 | Miscellaneous | Protection of carboxylic acid | 56520e0abb4535dce9a663824ca803b71c2c0dd72dfd246317d953596a987bd2 | 2ccc7a30191c2c171b49e8a0217bee87430687dd0f567141eca025a75b7e3136 | c1ccccc1 | [O;D1;H0:1]=[C:2](-[OH;D1;+0:3])-[c:4]>>[C;D1;H3:5]-[O;H0;D2;+0:3]-[C:2](=[O;D1;H0:1])-[c:4] | 99.3 | [{"value": 99.3, "product": "COC(C1=CC=C(C=C1)I)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Fifty (50) mmol (12.4 g) of commercially available 4-iodobenzoic acid was dissolved in 200 ml of tetrahydrofuran and then added to an ether solution containing freshly prepared diazomethane. The excess diazomethane was subsequently consumed by addition of glacial acetic acid and the resultant solution was concentrated ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1ccccc1 | Other | O1CCCC1 | null | null | O=C(O)c1ccc(I)cc1>O1CCCC1>COC(=O)c1ccc(I)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6c41a6072d6542949567036d24ed5e23 | C#CCO.COC(=O)c1ccc(I)cc1>>COC(=O)c1ccc(C#CCO)cc1 | IC1=CC=C(C(=O)OC)C=C1.C(C#C)O>>OCC#CC1=CC=C(C(=O)OC)C=C1 | [CH:9]#[C:10][CH2:11][OH:12].I[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:14][cH:13]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]#[C:10][CH2:11][OH:12])[cH:13][cH:14]1 | C#CCO.COC(=O)c1ccc(I)cc1 | COC(=O)c1ccc(C#CCO)cc1 | null | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | C(C)NCC | C-C Coupling | Sonogashira alkyne_aryl halide | 15c08902746c61a960c314898ce6bb5fcc5e189f9e057388c59dba9ec9d0c81c | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccccc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]#[CH;D1;+0:8]>>[C:6]-[C:7]#[C;H0;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 83.1 | [{"value": 83.0, "product": "OCC#CC1=CC=C(C(=O)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.1, "product": "OCC#CC1=CC=C(C(=O)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Methyl 4-iodobenzoate (9.0 g, 34.4 mmol) was dissolved in 90 ml of diethylamine. The solution was stirred vigorously and, sequentially, 121 milligrams of bis(triphenylphosphine) palladium chloride and 65 milligrams of cuprous iodide were added, each in a single portion, followed by 1.93 grams of propargyl alcohol. The ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccccc1 | c1ccccc1 | c1ccccc1 | HI | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)NCC | null | null | C#CCO.COC(=O)c1ccc(I)cc1>[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)NCC>COC(=O)c1ccc(C#CCO)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d7d51544825c4bb7a548bd1885f197b6 | O=C(CC(C(=O)O)C(=O)O)c1ccsc1>>O=C(O)CCCc1ccsc1 | [Na+].[Cl-].O.NN.[OH-].[K+].O=C(CC(C(=O)O)C(=O)O)C1=CSC=C1.Cl>>S1C=C(C=C1)CCCC(=O)O | O=C(O)[CH:4]([C:2](=[O:1])[OH:3])[CH2:5][C:6](=O)[c:7]1[cH:8][cH:9][s:10][cH:11]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][c:7]1[cH:8][cH:9][s:10][cH:11]1 | O=C(CC(C(=O)O)C(=O)O)c1ccsc1 | O=C(O)CCCc1ccsc1 | null | null | C(CO)O | Reduction | OtherReaction | 5b8f0395946b243f5d5c516ddfd2c7b17767fe5a6bd4d01b8d36e05474913824 | a54c4ff227377b63a7e5600277363bb31869ae720888ac22a37508be1aa77a21 | c1ccsc1 | O-C(=O)-[CH;D3;+0:1](-[C:2]-[C;H0;D3;+0:3](=O)-[c:4]1:[c:5]:[#16;a:6]:[c:7]:[c:8]:1)-[C:9](=[O;D1;H0:10])-[O;D1;H1:11]>>[O;D1;H0:10]=[C:9](-[O;D1;H1:11])-[CH2;D2;+0:1]-[C:2]-[CH2;D2;+0:3]-[c:4]1:[c:5]:[#16;a:6]:[c:7]:[c:8]:1 | 87.6 | [{"value": 87.6, "product": "S1C=C(C=C1)CCCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Hydrazine hydrate (1.3 mL, 1.34 g, 26.8 mmol) was added dropwise to a solution of KOH (3.54 g, 63 mmol) and 2-[2-oxo-2-(3-thienyl) ethyl]malonic acid 8(c) (4.00 g, 17.5 mmol) in ethylene glycol (30 mL). This solution was heated at reflux for 6 hours. After cooling to room temperature, the crude reaction mixture was pou... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | null | null | null | c1ccsc1 | Other | C(CO)O | null | null | O=C(CC(C(=O)O)C(=O)O)c1ccsc1>C(CO)O>O=C(O)CCCc1ccsc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-377a459ff6984e289cfcd5758d18e946 | NO.O=C1CCCc2ccccc21>>ON=C1CCCc2ccccc21 | C1(CCCC2=CC=CC=C12)=O.O.C(C)(=O)[O-].[Na+].Cl.NO>>C1(CCCC2=CC=CC=C12)=NO | [OH:1][NH2:2].O=[C:3]1[CH2:4][CH2:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]21>>[OH:1][N:2]=[C:3]1[CH2:4][CH2:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]21 | NO.O=C1CCCc2ccccc21 | ON=C1CCCc2ccccc21 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 98df1d319842c80da69615da3a5ce7c9aa877051ff6e5b7391db85d01092ee6d | 1a0ef15294bdb221fb8888b5d4c7fcf00473b11e53da288791d32747daa48d23 | N=C1CCCc2ccccc21 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[O;D1;H1:8]>>[C:3]-[C:2]-[C;H0;D3;+0:1](=[N;H0;D2;+0:7]-[O;D1;H1:8])-[c:4](:[c:5]):[c:6] | 95 | [{"value": 95.0, "product": "C1(CCCC2=CC=CC=C12)=NO", "details": "PERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 15 | MINUTE | To 4.6 L of water at room temperature in a 4-neck 50 L flask sitting in a steam bath apparatus equipped with an overhead stirrer, a temperature probe and reflux condenser was added 3.72 Kg (27.36 mol) of sodium acetate with stirring, followed by 1.9 Kg of hydroxylamine hydrochloride (27.36 mol). To this slurry at room ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Oxime | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | HO- | C(C)O | 75 | 0.25 | NO.O=C1CCCc2ccccc21>C(C)O>ON=C1CCCc2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bcec0cf5870e4b4b8e57365233ab30d8 | ON=C1CCCc2ccccc21>>O=C1CCCc2ccccc2N1 | C1(CCCC2=CC=CC=C12)=NO.CS(=O)(=O)O.O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3.[OH-].[Na+].CS(=O)(=O)O>>N1C(CCCC2=C1C=CC=C2)=O | [OH:1][N:12]=[C:2]1[CH2:3][CH2:4][CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]21>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[NH:12]1 | ON=C1CCCc2ccccc21 | O=C1CCCc2ccccc2N1 | null | null | null | Miscellaneous | OtherReaction | 3063b294f7182a0341159c5a5ab6dd2b1163127b2f088d9184b9c29e8afcfd24 | 810ed199c446b7a720678de08fbd331169d64180af03f0e0c66326af0c16570f | O=C1CCCc2ccccc2N1 | [OH;D1;+0:1]-[N;H0;D2;+0:2]=[C;H0;D3;+0:3]1-[C:4]-[C:5]-[C:6]-[c:7](:[c:8]):[c;H0;D3;+0:9]-1:[c:10]:[c:11]>>[O;H0;D1;+0:1]=[C;H0;D3;+0:3]1-[C:4]-[C:5]-[C:6]-[c:7](:[c:8]):[c;H0;D3;+0:9](:[c:10]:[c:11])-[NH;D2;+0:2]-1 | 95 | [{"value": 95.0, "product": "N1C(CCCC2=C1C=CC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 3 | HOUR | To 10 L of methanesulfonic acid in a 22 L 3-neck flask equipped with an overhead stirrer, a temperature probe, nitrogen inlet and reflux condenser was added 2.6 Kg (18.61 mol) of phosphorus pentoxide. An additional 1.6 L of methanesulfonic acid was used to wash all the phosphorus pentoxide into the vessel. The mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Oxime | Secondary amide | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCCN2 | c1ccc2c(c1)CCCCN2 | null | null | 90 | 3 | ON=C1CCCc2ccccc21>>O=C1CCCc2ccccc2N1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6d7bcd1e14f74813ae3d55bd0a8bbec4 | II.O=C1CCCc2ccccc2N1>>O=C1Nc2ccccc2CCC1I | N1C(CCCC2=C1C=CC=C2)=O.S(=O)([O-])[O-].[Na+].[Na+].S(=O)([O-])[O-].[Na+].[Na+].C[Si](N[Si](C)(C)C)(C)C.II>>IC1C(NC2=C(CC1)C=CC=C2)=O | I[I:13].[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[CH2:10][CH2:11][CH2:12]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[CH2:10][CH2:11][CH:12]1[I:13] | II.O=C1CCCc2ccccc2N1 | O=C1Nc2ccccc2CCC1I | null | null | C(Cl)Cl.O | Functional Group Interconversion | OtherReaction | 73a4b8101accc5821bcd407bb00b0d5a1b99828e455f6ca75099f6d3708d4163 | 0c353a1260488c22c3ffb72de5623420c3ec35470a0b3a2045b11c29224f458e | O=C1CCCc2ccccc2N1 | I-[I;H0;D1;+0:1].[C:2]-[C:3]-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#7:7]-[c:8]>>[C:2]-[C:3]-[CH;D3;+0:4](-[I;H0;D1;+0:1])-[C:5](=[O;D1;H0:6])-[#7:7]-[c:8] | 57.5 | [{"value": 57.0, "product": "IC1C(NC2=C(CC1)C=CC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.5, "product": "IC1C(NC2=C(CC1)C=CC=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 30 | CELSIUS | null | null | A suspension of 1.8 Kg (11.17 mol) of 2,3,4,5-tetrahydro-1H-1-benzazepin-2-one in a mixture of 22.33 L of methylene chloride and 11.78 L (55.83 mol) of hexamethyldisilazane was heated at reflux for 10 minutes then cooled to 30° C. and treated with 8.503 Kg (33.5 mol) of iodine in one portion. The mixture was heated at ... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary halide | c1ccc2c(c1)CCCCN2 | c1ccc2c(c1)CCCCN2 | c1ccc2c(c1)CCCCN2 | HI | C(Cl)Cl.O | 30 | null | II.O=C1CCCc2ccccc2N1>C(Cl)Cl.O>O=C1Nc2ccccc2CCC1I |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c735dcd09dc84541aa910c31a66677ea | CC(C)(C)OC(=O)N1C(=O)CC1(C)C.[OH-]>>CC(C)(CC(=O)O)NC(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)N1C(CC1(C)C)=O.[OH-].[Li+]>>C(C)(C)(C)OC(=O)NC(CC(=O)O)(C)C | [CH3:1][C:2]1([CH3:3])[CH2:4][C:5](=[O:6])[N:8]1[C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15].[OH-:7]>>[CH3:1][C:2]([CH3:3])([CH2:4][C:5](=[O:6])[OH:7])[NH:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15] | CC(C)(C)OC(=O)N1C(=O)CC1(C)C.[OH-] | CC(C)(CC(=O)O)NC(=O)OC(C)(C)C | null | null | CCOCC.O.O1CCCC1 | Protection | OtherReaction | 699e354eb5730d20a794b83d5cd440f6d8fa1c94b8fdaa5e255e70e482a7e50d | d205f1320160ea6fd9f0bda4863ee5979f7ad336699029216ee1832d3dc0743f | null | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[N;H0;D3;+0:8]1-[C;H0;D3;+0:9](=[O;D1;H0:10])-[C:11]-[C:12]-1(-[C;D1;H3:13])-[C;D1;H3:14].[OH-;D0:15]>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[NH;D2;+0:8]-[C:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[C:11]-[C;H0;D3;+0:9]... | 87 | [{"value": 87.0, "product": "C(C)(C)(C)OC(=O)NC(CC(=O)O)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A 3 L, 3-neck round bottom flask equipped with a magnetic stirrer, thermometer, nitrogen bubbler and addition funnel was charged with 180.3 g (0.89 mol) of N-(t-butoxycarbonyl)-4,4-dimethylazetidin-2-one dissolved in 1 L of tetrahydrofuran. The solution was cooled to 0°-5° C. and treated dropwise with 890 mL of 1.0M aq... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Substituted dicarboximide | Carbamic ester.Carboxylic acid | C1C[NH]C1 | null | null | null | CCOCC.O.O1CCCC1 | null | 2 | CC(C)(C)OC(=O)N1C(=O)CC1(C)C.[OH-]>CCOCC.O.O1CCCC1>CC(C)(CC(=O)O)NC(=O)OC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-48cc48b39ac845098b60f3e2837e0e56 | CC(C)(CC(=O)O)NC(=O)OC(C)(C)C.N[C@@H]1CCc2ccccc2NC1=O>>CC(C)(CC(=O)N[C@@H]1CCc2ccccc2NC1=O)NC(=O)OC(C)(C)C | F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.N[C@H]1C(NC2=C(CC1)C=CC=C2)=O.C(C)(C)(C)OC(=O)NC(CC(=O)O)(C)C.C(C)N(CC)CC>>C(C)(C)(C)OC(=O)NC(CC(=O)N[C@H]1C(NC2=C(CC1)C=CC=C2)=O)(C)C | O[C:5]([CH2:4][C:2]([CH3:1])([CH3:3])[NH:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:6].[NH2:7][C@@H:8]1[CH2:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[NH:17][C:18]1=[O:19]>>[CH3:1][C:2]([CH3:3])([CH2:4][C:5](=[O:6])[NH:7][C@@H:8]1[CH2:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[NH... | CC(C)(CC(=O)O)NC(=O)OC(C)(C)C.N[C@@H]1CCc2ccccc2NC1=O | CC(C)(CC(=O)N[C@@H]1CCc2ccccc2NC1=O)NC(=O)OC(C)(C)C | null | null | C(Cl)Cl.C(C)(=O)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1CCCc2ccccc2N1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6](-[NH2;D1;+0:7])-[C:8](=[O;D1;H0:9])-[#7:10]-[c:11]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6](-[C:5])-[C:8](=[O;D1;H0:9])-[#7:10]-[c:11] | 94 | [{"value": 94.0, "product": "C(C)(C)(C)OC(=O)NC(CC(=O)N[C@H]1C(NC2=C(CC1)C=CC=C2)=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.9, "product": "C(C)(C)(C)OC(=O)NC(CC(=O)N[C@H]1C(NC2=C(CC1)C=CC=C2)=O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 8.70 g (49.4 mmol) of 3(R)-amino-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (Step E) in 100 mL of methylene chloride was treated with 10.73 g (49.4 mmol) of 3-t-butoxycarbonylamino-3-methylbutanoic acid (Step H) and 13.8 mL of triethylamine (10.0 g, 99 mmol, 2 eq.). The reaction flask was immersed in an amb... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2c(c1)CCCCN2 | HO- | C(Cl)Cl.C(C)(=O)OCC | null | 2 | CC(C)(CC(=O)O)NC(=O)OC(C)(C)C.N[C@@H]1CCc2ccccc2NC1=O>C(Cl)Cl.C(C)(=O)OCC>CC(C)(CC(=O)N[C@@H]1CCc2ccccc2NC1=O)NC(=O)OC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ead516c1b5b84915b6f58d3f44f1f181 | C=O.Cc1ccc(O)cc1>>Cc1ccc(O)c(C=O)c1 | C1(=CC=CC=C1)C.C=O.C[Mg]Cl.C1=CC(=CC=C1O)C>>OC1=C(C=O)C=C(C=C1)C | [CH2:8]=[O:9].[CH3:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[cH:7][cH:10]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[c:7]([CH:8]=[O:9])[cH:10]1 | C=O.Cc1ccc(O)cc1 | Cc1ccc(O)c(C=O)c1 | null | CN1C(N(CCC1)C)=O | O1CCCC1 | C-C Coupling | OtherReaction | 6bafee88871e7df55b2a6a706a8a62d4f54a2873abef1ac73ed67da72b977665 | 0102b88d9700d39435e06971744797a0ad3df95b36c61ce095d6702bc41b05ed | c1ccccc1 | [CH2;D1;+0:1]=[O;D1;H0:2].[O;D1;H1:3]-[c:4](:[c:5]):[cH;D2;+0:6]:[c:7]:[c:8]>>[O;D1;H0:2]=[CH;D2;+0:1]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:4](-[O;D1;H1:3]):[c:5] | 18 | [{"value": 18.0, "product": "OC1=C(C=O)C=C(C=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 18.0, "product": "OC1=C(C=O)C=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Methylmagnesium chloride solution in tetrahydrofuran (100 mL, 3.0M, 300 mmol) at room temperature was treated dropwise over 30 minutes with a solution of 32.3 g (300 mmol) of p-cresol in 30 mL of tetrahydrofuran. An additional 70 mL of tetrahydrofuran was added to moderate the exothermic reaction. The mixture was aged ... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde | Aldehyde | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | CN1C(N(CCC1)C)=O.O1CCCC1 | null | 2 | C=O.Cc1ccc(O)cc1>CN1C(N(CCC1)C)=O.O1CCCC1>Cc1ccc(O)c(C=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6c59e00fa9b34294a8339d168dc3dcaa | Cc1ccc(O)c(C=O)c1.N#Cc1ccccc1CBr>>Cc1ccc2oc(-c3ccccc3C#N)cc2c1 | C[O-].[Na+].BrCC=1C(=CC=CC1)C#N.OC1=C(C=O)C=C(C=C1)C.C[O-].[Na+].C(C)O>>C(#N)C1=C(C=CC=C1)C=1OC2=C(C1)C=C(C=C2)C | O=[CH:16][c:17]1[c:5]([OH:6])[cH:4][cH:3][c:2]([CH3:1])[cH:18]1.Br[CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[C:14]#[N:15]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[o:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[C:14]#[N:15])[cH:16][c:17]2[cH:18]1 | Cc1ccc(O)c(C=O)c1.N#Cc1ccccc1CBr | Cc1ccc2oc(-c3ccccc3C#N)cc2c1 | null | null | CN(C=O)C.O | Aromatic Heterocycle Formation | OtherReaction | ae0d8af73753cd90bad163caf180a20dbba0089f4ad123713353f52ec702d104 | 92cc8b0a92f96eb9b03a03a2ee19d09e7e6c24351b1bf5fbd10085af3332d8a0 | c1ccc(-c2cc3ccccc3o2)cc1 | Br-[CH2;D2;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5](-[C:6]#[N;D1;H0:7]):[c:8].O=[CH;D2;+0:9]-[c:10](:[c:11]):[c:12](-[OH;D1;+0:13]):[c:14]>>[N;D1;H0:7]#[C:6]-[c:5](:[c:8]):[c;H0;D3;+0:2](-[c;H0;D3;+0:1]1:[cH;D2;+0:9]:[c:10](:[c:11]):[c:12](:[c:14]):[o;H0;D2;+0:13]:1):[c:3]:[c:4] | 63.3 | [{"value": 63.0, "product": "C(#N)C1=C(C=CC=C1)C=1OC2=C(C1)C=C(C=C2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.3, "product": "C(#N)C1=C(C=CC=C1)C=1OC2=C(C1)C=C(C=C2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 20 | MINUTE | A 500 mL 3-neck round bottom flask equipped with a magnetic stirrer, dropping funnel, thermometer and nitrogen bubbler was charged with 10.7 g (108 mmol) of sodium methoxide and 75 mL of absolute ethanol. A solution of 24.9 g (183 mmol) of 2-hydroxy-5-methylbenzaldehyde in 75 mL of dry dimethylformamide was added dropw... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aldehyde.Aromatic alcohol | null | c1ccccc1 | c1ccc2occc2c1 | c1ccc2occc2c1.c1ccccc1 | HBr | CN(C=O)C.O | 75 | 0.333333 | Cc1ccc(O)c(C=O)c1.N#Cc1ccccc1CBr>CN(C=O)C.O>Cc1ccc2oc(-c3ccccc3C#N)cc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a70c972de63c48c88aee846896f01c2b | Cc1ccc2oc(-c3ccccc3C#N)cc2c1.[CH3][Sn]([CH3])([CH3])[N]=[N+]=[N-]>>Cc1ccc2oc(-c3ccccc3-c3nnn[nH]3)cc2c1 | C[Sn](C)(C)N=[N+]=[N-].C[Sn](C)(C)N=[N+]=[N-].C(#N)C1=C(C=CC=C1)C=1OC2=C(C1)C=C(C=C2)C.C[Sn](C)(C)N=[N+]=[N-]>>N1N=NN=C1C1=C(C=CC=C1)C=1OC2=C(C1)C=C(C=C2)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]2[o:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[C:14]#[N:15])[cH:19][c:20]2[cH:21]1.[CH3][Sn]([CH3])([CH3])[N:18]=[N+:17]=[N-:16]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[o:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3-[c:14]3[n:15][n:16][n:17][nH:18]3)[cH:19][c:20]2[cH:21]1 | Cc1ccc2oc(-c3ccccc3C#N)cc2c1.[CH3][Sn]([CH3])([CH3])[N]=[N+]=[N-] | Cc1ccc2oc(-c3ccccc3-c3nnn[nH]3)cc2c1 | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | d793d4dee9d5a39dbd122d04a35a5f691674657d5f6e422ae31ce158ea438a57 | 95e338ac8e3158e8ab88ebe03ba7338cec0c32ed80de2cb9f73834a6f54aede3 | c1ccc(-c2cc3ccccc3o2)c(-c2nnn[nH]2)c1 | [#8;a:1]:[c:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[C;H0;D2;+0:6]#[N;H0;D1;+0:7]):[c:8]:[c:9].[CH3]-[Sn](-[CH3])(-[CH3])-[N;H0;D2;+0:10]=[N+;H0;D2:11]=[N-;H0;D1:12]>>[#8;a:1]:[c:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[c;H0;D3;+0:6]1:[n;H0;D2;+0:7]:[n;H0;D2;+0:12]:[n;H0;D2;+0:11]:[nH;D2;+0:10]:1):[c:8]:[c:9] | 57.3 | [{"value": 57.0, "product": "N1N=NN=C1C1=C(C=CC=C1)C=1OC2=C(C1)C=C(C=C2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.3, "product": "N1N=NN=C1C1=C(C=CC=C1)C=1OC2=C(C1)C=C(C=C2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A 500 mL 3-neck round bottom flask equipped with a magnetic stirrer, condenser, thermometer and nitrogen bubbler was charged with 19.1 g (82 mmol) of 2-(2-cyanophenyl)-5-methylbenzofuran, 200 mL of toluene and 25.6 g (124 mmol) of trimethyltin azide. The suspension was heated at reflux for 20 hours, then an additional ... | 10.6084/m9.figshare.5104873.v1 | null | Azide.Nitrile.Tin | null | null | c1nnn[nH]1 | c1ccc2occc2c1.c1ccccc1.c1nnn[nH]1 | Sn | C1(=CC=CC=C1)C | null | 24 | Cc1ccc2oc(-c3ccccc3C#N)cc2c1.[CH3][Sn]([CH3])([CH3])[N]=[N+]=[N-]>C1(=CC=CC=C1)C>Cc1ccc2oc(-c3ccccc3-c3nnn[nH]3)cc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c9728215e0934ce58de5aa5e0e1a5863 | BrBr.Cc1ccc2oc(-c3ccccc3-c3nnn[nH]3)cc2c1>>Cc1ccc2oc(-c3ccccc3-c3nnn[nH]3)c(Br)c2c1 | C1=CCCCC1.BrBr.N1N=NN=C1C1=C(C=CC=C1)C=1OC2=C(C1)C=C(C=C2)C.O1CCOCC1>>BrC1=C(OC2=C1C=C(C=C2)C)C2=C(C=CC=C2)C2=NN=NN2 | Br[Br:20].[CH3:1][c:2]1[cH:3][cH:4][c:5]2[o:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3-[c:14]3[n:15][n:16][n:17][nH:18]3)[cH:19][c:21]2[cH:22]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[o:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3-[c:14]3[n:15][n:16][n:17][nH:18]3)[c:19]([Br:20])[c:21]2[cH:22]1 | BrBr.Cc1ccc2oc(-c3ccccc3-c3nnn[nH]3)cc2c1 | Cc1ccc2oc(-c3ccccc3-c3nnn[nH]3)c(Br)c2c1 | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Bromination | aef34a534a5357a8d8d24e91d8c0597ba5461b904c5f6750301da171e41c6efd | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc(-c2cc3ccccc3o2)c(-c2nnn[nH]2)c1 | Br-[Br;H0;D1;+0:1].[c:2]:[c:3]1:[cH;D2;+0:4]:[c:5](-[c:6]):[#8;a:7]:[c:8]:1:[c:9]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:4]1:[c:3](:[c:2]):[c:8](:[c:9]):[#8;a:7]:[c:5]:1-[c:6] | 85 | [{"value": 85.0, "product": "BrC1=C(OC2=C1C=C(C=C2)C)C2=C(C=CC=C2)C2=NN=NN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.6, "product": "BrC1=C(OC2=C1C=C(C=C2)C)C2=C(C=CC=C2)C2=NN=NN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A 1 L 3-neck round bottom flask equipped with a magnetic stirrer, thermometer, dropping funnel and nitrogen bubbler was charged with 12.97 g (46.9 mmol) of 2-[2-(1H-tetrazol-5-yl)phenyl]-5-methylbenzofuran and 500 mL of 1,4-dioxane. To the well-stirred solution at room temperature was added a solution of 4.8 mL (93.2 m... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2occc2c1 | c1ccc2occc2c1 | c1ccc2occc2c1.c1ccccc1.c1nnn[nH]1 | HBr | C(Cl)(Cl)(Cl)Cl | null | null | BrBr.Cc1ccc2oc(-c3ccccc3-c3nnn[nH]3)cc2c1>C(Cl)(Cl)(Cl)Cl>Cc1ccc2oc(-c3ccccc3-c3nnn[nH]3)c(Br)c2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-29db157c047e49c9aec1fa6bbd5e3bdc | O=C(O)CNC(=O)c1nc2cc(Cl)c(OCC(F)(F)F)cc2cc1O>>Cl.O=C(O)CNC(=O)c1nc2ccc(OCC(F)(F)F)cc2cc1O | ClC1=C(C=C2C=C(C(=NC2=C1)C(=O)NCC(=O)O)O)OCC(F)(F)F>>Cl.OC=1C(=NC2=CC=C(C=C2C1)OCC(F)(F)F)C(=O)NCC(=O)O | [Cl:1][c:13]1[cH:12][c:11]2[n:10][c:9]([C:7]([NH:6][CH2:5][C:3](=[O:2])[OH:4])=[O:8])[c:24]([OH:25])[cH:23][c:22]2[cH:21][c:14]1[O:15][CH2:16][C:17]([F:18])([F:19])[F:20]>>[ClH:1].[O:2]=[C:3]([OH:4])[CH2:5][NH:6][C:7](=[O:8])[c:9]1[n:10][c:11]2[cH:12][cH:13][c:14]([O:15][CH2:16][C:17]([F:18])([F:19])[F:20])[cH:21][c:22... | O=C(O)CNC(=O)c1nc2cc(Cl)c(OCC(F)(F)F)cc2cc1O | Cl.O=C(O)CNC(=O)c1nc2ccc(OCC(F)(F)F)cc2cc1O | null | null | C(=O)O | Reduction | Aromatic dehalogenation | eb8f97868eda2cc61388d201749d19c211b03c524acdc08748ef282eeabfb54b | 32dd8b99ef466a65369cb3d0423332250d968cb6028b4894311fd2c39ad8dfd2 | c1ccc2ncccc2c1 | [#7:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#7;a:5]:[c:6]1:[c:7]:[c;H0;D3;+0:8](-[Cl;H0;D1;+0:9]):[c:10](-[#8:11]):[c:12]:[c:13]:1>>[#7:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#7;a:5]:[c:6]1:[c:7]:[cH;D2;+0:8]:[c:10](-[#8:11]):[c:12]:[c:13]:1.[ClH;D0;+0:9] | null | [] | null | null | null | null | 0.5 g (1.3 mmol) of N-((7-chloro-3-hydroxy-6-(2,2,2-trifluoroethyloxy)quinolin-2-yl)carbonyl)glycine (title compound from Example 31) was dissolved in 26 ml of methanolic formic acid (4.4% strength), and a further 26 ml of methanolic formic acid were added at 20° C. After addition of 0.5 g of Pd/C (10%), the mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | null | C(=O)O | null | null | O=C(O)CNC(=O)c1nc2cc(Cl)c(OCC(F)(F)F)cc2cc1O>C(=O)O>Cl.O=C(O)CNC(=O)c1nc2ccc(OCC(F)(F)F)cc2cc1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a19347c988eb4c1c9861adc66fd17858 | O=C(O)c1cccc(OC(F)(F)F)c1.O=[N+]([O-])O>>O=C(O)c1cc(OC(F)(F)F)ccc1[N+](=O)[O-] | [N+](=O)(O)[O-].S(O)(O)(=O)=O.FC(OC=1C=C(C(=O)O)C=CC1)(F)F>>[N+](=O)([O-])C1=C(C(=O)O)C=C(C=C1)OC(F)(F)F | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([O:7][C:8]([F:9])([F:10])[F:11])[cH:12][cH:13][cH:14]1.O[N+:15](=[O:16])[O-:17]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([O:7][C:8]([F:9])([F:10])[F:11])[cH:12][cH:13][c:14]1[N+:15](=[O:16])[O-:17] | O=C(O)c1cccc(OC(F)(F)F)c1.O=[N+]([O-])O | O=C(O)c1cc(OC(F)(F)F)ccc1[N+](=O)[O-] | null | null | null | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccccc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[O;D1;H0:4]=[C:5](-[O;D1;H1:6])-[c:7](:[c:8]):[cH;D2;+0:9]:[c:10]:[c:11]>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:7](-[C:5](=[O;D1;H0:4])-[O;D1;H1:6]):[c:8] | null | [] | null | null | null | null | 29.7 ml of nitric acid were added dropwise to 76.5 ml of concentrated sulfuric acid, while cooling and stirring, and 9.0 g (43.7 mmol) of 3-trifluoromethoxybenzoic acid were then added. The reaction mixture was heated at 50°-55° C. for 1 hour and, after cooling, was poured onto ice, and the residue was filtered off wit... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | null | null | O=C(O)c1cccc(OC(F)(F)F)c1.O=[N+]([O-])O>>O=C(O)c1cc(OC(F)(F)F)ccc1[N+](=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-61857a4aa4ad49af8aac9e9223a18f71 | CC(C)I.O=[N+]([O-])c1ccc(O)cc1CO>>CC(C)Oc1ccc([N+](=O)[O-])c(CO)c1 | OC=1C=CC(=C(CO)C1)[N+](=O)[O-].C(C)(C)I>>[N+](=O)([O-])C1=C(CO)C=C(C=C1)OC(C)C | I[CH:2]([CH3:1])[CH3:3].[OH:4][c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[c:12]([CH2:13][OH:14])[cH:15]1>>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[c:12]([CH2:13][OH:14])[cH:15]1 | CC(C)I.O=[N+]([O-])c1ccc(O)cc1CO | CC(C)Oc1ccc([N+](=O)[O-])c(CO)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | bff4876be49b448135c783dd3eeeb68ab3cc5bdc91beadda8a9095106cd5c747 | cf768afb66ed5041aefdce1fa6d1e40995a1ab7c4b4a4ca47544fe49ee1e629f | c1ccccc1 | I-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[CH;D3;+0:1](-[C;D1;H3:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | 10 g (60 mmol) of 5-hydroxy-2-nitrobenzyl alcohol were reacted with 7.0 ml (70 mmol) of isopropyl iodide analogously to Example 4a); after purification over silica gel with n-heptane/ethyl acetate (3:2), 10.3 g of oily crude product.
Conditions: See reaction.notes.procedure_details.
Workup: after purification over sili... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HI | null | null | null | CC(C)I.O=[N+]([O-])c1ccc(O)cc1CO>>CC(C)Oc1ccc([N+](=O)[O-])c(CO)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dd95acbc02174382a8fb617b567ae3bb | CCCCCCC.NCC(=O)OCc1ccccc1.O=C(O)c1ccc2ccccc2n1>>CC(C)Oc1ccc2nc(C(=O)O)c(OCc3ccccc3)cc2c1 | CCCCCCC.C(C)(=O)OCC.N1=C(C=CC2=CC=CC=C12)C(=O)O.S(=O)(=O)(O)C1=CC=C(C)C=C1.C(C1=CC=CC=C1)OC(CN)=O.C=1C=CC2=C(C1)N=NN2O>>C(C1=CC=CC=C1)OC=1C(=NC2=CC=C(C=C2C1)OC(C)C)C(=O)O | CCCC[CH2:3][CH2:2][CH3:1].NC[C:14](=[O:4])[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.c1[c:10]([C:11](=[O:12])[OH:13])[n:9][c:8]2[cH:7][cH:6][cH:5][cH:25][c:24]2[cH:23]1>>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][cH:7][c:8]2[n:9][c:10]([C:11](=[O:12])[OH:13])[c:14]([O:15][CH2:16][c:17]3[cH:18][cH:19][cH:20]... | CCCCCCC.NCC(=O)OCc1ccccc1.O=C(O)c1ccc2ccccc2n1 | CC(C)Oc1ccc2nc(C(=O)O)c(OCc3ccccc3)cc2c1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 2b199ec13aedb354aa0e3cdfe102b222aae079ed256cd671f480c20ceec4f336 | 5769fcad2252788e49992e3c2acac5e3ae32b3811010bcf6e71d6b058fc9a9df | c1ccc(COc2cnc3ccccc3c2)cc1 | C-C-C-C-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[C;D1;H3:3].N-C-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[#8:6]-[C:7].[O;D1;H0:8]=[C:9](-[O;D1;H1:10])-[c;H0;D3;+0:11]1:[#7;a:12]:[c:13]2:[c:14]:[c:15]:[cH;D2;+0:16]:[c:17]:[c:18]:2:[cH;D2;+0:19]:c:1>>[C:7]-[#8:6]-[c;H0;D3;+0:4]1:[cH;D2;+0:19]:[c:18]2:[c:17]:[c;H0;D3;+0:16](-[O;H0;D2;+0:5]-[C... | 129.7 | [{"value": 129.7, "product": "C(C1=CC=CC=C1)OC=1C(=NC2=CC=C(C=C2C1)OC(C)C)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2.7 g (8 mmol) of the above quinolinecarboxylic acid were reacted with 2.7 g (8 mmol) of glycine benzyl ester tosylate, 4.4 ml (32 mmol) of NEM, 1.35 g (10 mmol) of HOBT and 3.6 g (8.8 mmol) of CMC in 300 ml of anhydrous methylene chloride at 20° C. for 24 hours, analogously to Example 25g). After working up and chroma... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Ether.Ether | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1 | Other | C(Cl)Cl | null | null | CCCCCCC.NCC(=O)OCc1ccccc1.O=C(O)c1ccc2ccccc2n1>C(Cl)Cl>CC(C)Oc1ccc2nc(C(=O)O)c(OCc3ccccc3)cc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7ccd2207c11e4dc982df4da8ca022082 | Cc1cc(F)ccc1[N+](=O)[O-].Oc1ccccc1>>Cc1cc(Oc2ccccc2)ccc1[N+](=O)[O-] | C1(=CC=CC=C1)O.C([O-])([O-])=O.[K+].[K+].FC=1C=CC(=C(C1)C)[N+](=O)[O-]>>[N+](=O)([O-])C1=C(C=C(C=C1)OC1=CC=CC=C1)C | F[c:4]1[cH:3][c:2]([CH3:1])[c:14]([N+:15](=[O:16])[O-:17])[cH:13][cH:12]1.[OH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[CH3:1][c:2]1[cH:3][c:4]([O:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[cH:12][cH:13][c:14]1[N+:15](=[O:16])[O-:17] | Cc1cc(F)ccc1[N+](=O)[O-].Oc1ccccc1 | Cc1cc(Oc2ccccc2)ccc1[N+](=O)[O-] | null | null | CN(C(C)=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | e4ea1e38252bc3b9c5ec04486386725e6570ab3860d45e337a1d131319bbf0fc | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccccc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[O;H0;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9] | null | [] | 20 | CELSIUS | null | null | 14.1 g (150 mmol) of phenol were dissolved in 120 ml of anhydrous N,N-dimethylacetamide, while stirring, 20.6 g (150 mmol) of finely powdered potassium carbonate were added and the mixture was stirred at 70°-80° C. for 30 minutes. After cooling to 20° C., 23.25 g (18.3 ml, 150 mmol) of 5-fluoro-2-nitrotoluene were adde... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | CN(C(C)=O)C | 20 | null | Cc1cc(F)ccc1[N+](=O)[O-].Oc1ccccc1>CN(C(C)=O)C>Cc1cc(Oc2ccccc2)ccc1[N+](=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9998629522e842d089f0d1c3f6b90263 | Cc1ccc(Cl)c(Cl)c1.O=[N+]([O-])O>>Cc1cc(Cl)c(Cl)cc1[N+](=O)[O-] | ClC=1C=C(C=CC1Cl)C.S(O)(O)(=O)=O.[N+](=O)(O)[O-]>>ClC1=CC(=C(C=C1Cl)C)[N+](=O)[O-] | [CH3:1][c:2]1[cH:3][c:4]([Cl:5])[c:6]([Cl:7])[cH:8][cH:9]1.O[N+:10](=[O:11])[O-:12]>>[CH3:1][c:2]1[cH:3][c:4]([Cl:5])[c:6]([Cl:7])[cH:8][c:9]1[N+:10](=[O:11])[O-:12] | Cc1ccc(Cl)c(Cl)c1.O=[N+]([O-])O | Cc1cc(Cl)c(Cl)cc1[N+](=O)[O-] | null | null | null | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccccc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[C;D1;H3:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[C;D1;H3:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]):[c:8]:[c:9] | null | [] | null | null | null | null | 3,4-Dichlorotoluene was nitrated with concentrated sulfuric acid and fuming nitric acid (d=1.52).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | null | null | Cc1ccc(Cl)c(Cl)c1.O=[N+]([O-])O>>Cc1cc(Cl)c(Cl)cc1[N+](=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5c297b4a87b04776a1276a465dc94abc | Cc1cc(Cl)c(Cl)cc1[N+](=O)[O-].OCC(F)(F)F>>Cc1cc(OCC(F)(F)F)c(Cl)cc1[N+](=O)[O-] | CC(C)(C)[O-].[K+].C(C(F)(F)F)O.ClC1=CC(=C(C=C1Cl)C)[N+](=O)[O-]>>ClC1=CC(=C(C=C1OCC(F)(F)F)C)[N+](=O)[O-] | Cl[c:4]1[cH:3][c:2]([CH3:1])[c:14]([N+:15](=[O:16])[O-:17])[cH:13][c:11]1[Cl:12].[OH:5][CH2:6][C:7]([F:8])([F:9])[F:10]>>[CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][C:7]([F:8])([F:9])[F:10])[c:11]([Cl:12])[cH:13][c:14]1[N+:15](=[O:16])[O-:17] | Cc1cc(Cl)c(Cl)cc1[N+](=O)[O-].OCC(F)(F)F | Cc1cc(OCC(F)(F)F)c(Cl)cc1[N+](=O)[O-] | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 4821d6d7238522ee9ef4538c00647e855becf4de3d9c939c0cec2b01c1e5e915 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccccc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6].[F;D1;H0:7]-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[C:11]-[OH;D1;+0:12]>>[Cl;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[O;H0;D2;+0:12]-[C:11]-[C:8](-[F;D1;H0:7])(-[F;D1;H0:9])-[F;D1;H0:10]):[c:2]:[c:3] | null | [] | null | null | null | null | 40.4 g (360 mmol) of potassium tert-butylate were added in portions to 60 ml of trifluoroethanol, while stirring and cooling, and the mixture was heated to 80°-90° C. After cooling, 14.4 g (70 mmol) of 4,5-dichloro-2-nitrotoluene were added and the mixture was stirred at 105° C. for 1 hour. It was concentrated in vacuo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | null | null | null | Cc1cc(Cl)c(Cl)cc1[N+](=O)[O-].OCC(F)(F)F>>Cc1cc(OCC(F)(F)F)c(Cl)cc1[N+](=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0d0cde9f744f4003bee69dc9e97ec82e | NCC(=O)N1CCC[C@H]1C(=O)N1C[C@H](O)C[C@H]1C(=O)O.O=C(OCC1c2ccccc2-c2ccccc21)ON1C(=O)CCC1=O>>O=C(NCC(=O)N1CCC[C@H]1C(=O)N1C[C@H](O)C[C@H]1C(=O)O)OCC1c2ccccc2-c2ccccc21 | C(=O)([O-])[O-].[Na+].[Na+].C(OCC1C2=CC=CC=C2C=2C=CC=CC12)(ON1C(CCC1=O)=O)=O.NCC(=O)N1[C@H](C(=O)N2[C@H](C(=O)O)C[C@@H](O)C2)CCC1.NCC(=O)N1[C@H](C(=O)N2[C@H](C(=O)O)C[C@@H](O)C2)CCC1>>N(CC(=O)N1[C@H](C(=O)N2[C@H](C(=O)O)C[C@@H](O)C2)CCC1)C(=O)OCC1C2=CC=CC=C2C2=CC=CC=C12 | [NH2:3][CH2:4][C:5](=[O:6])[N:7]1[CH2:8][CH2:9][CH2:10][C@H:11]1[C:12](=[O:13])[N:14]1[CH2:15][C@H:16]([OH:17])[CH2:18][C@H:19]1[C:20](=[O:21])[OH:22].O=C1CCC(=O)N1O[C:2](=[O:1])[O:23][CH2:24][CH:25]1[c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]2-[c:32]2[cH:33][cH:34][cH:35][cH:36][c:37]21>>[O:1]=[C:2]([NH:3][CH2:4][C:5](=... | NCC(=O)N1CCC[C@H]1C(=O)N1C[C@H](O)C[C@H]1C(=O)O.O=C(OCC1c2ccccc2-c2ccccc21)ON1C(=O)CCC1=O | O=C(NCC(=O)N1CCC[C@H]1C(=O)N1C[C@H](O)C[C@H]1C(=O)O)OCC1c2ccccc2-c2ccccc21 | null | null | C(OC)COC.C(=O)([O-])[O-].[Na+].[Na+].O | Protection | OtherReaction | 90f1cd2cfb4916c247fdb0b8c4bcd653fe37fb375d251f3afd49969111cee737 | f7ec1d72774a3155b06d1cf24e018b58f69117ddf4d9559df84efc3ecef0f4d7 | O=C(NCC(=O)N1CCC[C@H]1C(=O)N1CCCC1)OCC1c2ccccc2-c2ccccc21 | O=C1-C-C-C(=O)-N-1-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-[#7:9](-[C:10](=[O;D1;H0:11])-[C:12]-[NH2;D1;+0:13])-[C:14]>>[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-[#7:9](-[C:10](=[O;D1;H0:11])-[C:12]-[NH;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4])-[C:14] | null | [] | 4 | CELSIUS | 21 | HOUR | Fmoc-Gly-Pro-Hyp was synthesized from Gly-Pro-Hyp as follows: 3.0 g Gly-Pro-Hyp (10.5 mmol) was dissolved in 54 mL Na2CO3 --H2O (1:9) and stored at 4° C. 4.05 g 9-fluorenylmethyl succinimidyl carbonate (12.0 mmol) was dissolved in 45 mL dimethoxyethane and stirred at 4° C. The aqueous Na2CO3 solution was added slowly t... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Tertiary amide.Tertiary amide.Primary amine | Carbamic ester | C1CCNC1 | null | C1CC[NH]C1.C1CC[NH]C1.c1ccc2c(c1)Cc1ccccc12 | HO- | C(OC)COC.C(=O)([O-])[O-].[Na+].[Na+].O | 4 | 21 | NCC(=O)N1CCC[C@H]1C(=O)N1C[C@H](O)C[C@H]1C(=O)O.O=C(OCC1c2ccccc2-c2ccccc21)ON1C(=O)CCC1=O>C(OC)COC.C(=O)([O-])[O-].[Na+].[Na+].O>O=C(NCC(=O)N1CCC[C@H]1C(=O)N1C[C@H](O)C[C@H]1C(=O)O)OCC1c2ccccc2-c2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c1ba761e373b418eb88a318c26b3d7f2 | CCCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O.O=C(O)CNC(=O)OCC1c2ccccc2-c2ccccc21>>C=CCC(=O)CNC(=O)OCC1c2ccccc2-c2ccccc21 | N(CC(=O)O)C(=O)OCC1C2=CC=CC=C2C2=CC=CC=C12.C=1C=CC2=C(C1)N=NN2O.CC(C)N=C=NC(C)C.N([C@@H](CCCC)C(=O)O)C(=O)OCC1C2=CC=CC=C2C2=CC=CC=C12.CC1=CC=C(C=C1)C(C2=CC=CC=C2)N.C=CC1=CC=CC=C1.C=CC1=CC=C(C=C1)C=C.Cl.C=1C=CC2=C(C1)N=NN2O.CC(C)N=C=NC(C)C.C=1C=CC2=C(C1)N=NN2O.CC(C)N=C=NC(C)C>>N(CC(=O)CC=C)C(=O)OCC1C2=CC=CC=C2C2=CC=CC=C... | CC[CH2:2][CH2:3][C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O.O[C:4](=[O:5])[CH2:6][NH:7][C:8](=[O:9])[O:10][CH2:11][CH:12]1[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2-[c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]21>>[CH2:1]=[CH:2][CH2:3][C:4](=[O:5])[CH2:6][NH:7][C:8](=[O:9])[O:10][CH2:11][CH:12]1[c:13]2[cH:14][cH:15][cH:16][c... | CCCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O.O=C(O)CNC(=O)OCC1c2ccccc2-c2ccccc21 | C=CCC(=O)CNC(=O)OCC1c2ccccc2-c2ccccc21 | null | CN(C)C=1C=CN=CC1 | CN(C)C=O.C(Cl)Cl.CN(C)C=O | C-C Coupling | OtherReaction | 0eca1684da96ab67dce1b14f1cbf2209808af72c025b7fb12a2f1f73d35240c3 | 3eae7e4d25d89a062e55e5b9951a7233e3647040f5b5a06988852b724cfdebae | c1ccc2c(c1)Cc1ccccc1-2 | C-C-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[C@H](-N-C(=O)-O-C-C1-c2:c:c:c:c:c:2-c2:c:c:c:c:c:2-1)-C(-O)=O.O-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C:5]-[#7:6]-[C:7]=[O;D1;H0:8]>>[C;D1;H2:9]=[CH;D2;+0:1]-[CH2;D2;+0:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C:5]-[#7:6]-[C:7]=[O;D1;H0:8] | null | [] | null | null | 30 | MINUTE | 0.848 g Fmoc-Nle (2.4 mmol) was coupled to 2.0 g MBHA resin (1.6 mmol) with 0.367 g HOBt (2.4 mmol) and 0.373 mL DIPCDI (2.4 mmol) in 20 mL DCM-DMF (1:1) for 2.3 h. The resin was washed 3 times with DMF, deprotected with 20 mL piperidine-DMF (1:1) for 30 min, and washed 3 times with DMF. 1.82 g allyl linker (3.2 mmol) ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Carboxylic acid.Ether | Ketone.Allyl | c1ccc2c(c1)Cc1ccccc12 | null | c1ccc2c(c1)Cc1ccccc12 | HO- | CN(C)C=1C=CN=CC1.CN(C)C=O.C(Cl)Cl.CN(C)C=O | null | 0.5 | CCCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O.O=C(O)CNC(=O)OCC1c2ccccc2-c2ccccc21>CN(C)C=1C=CN=CC1.CN(C)C=O.C(Cl)Cl.CN(C)C=O>C=CCC(=O)CNC(=O)OCC1c2ccccc2-c2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f12406699295447fa245b2a1d83d7703 | BrCCBr.COc1ccc(Br)cc1.[Mg]>>COc1ccc([CH2][Mg][Br])cc1 | BrC1=CC=C(C=C1)OC.[Mg].II.C1CCOC1.BrCCBr>>C(C1=CC=C(C=C1)OC)[Mg]Br | BrC[CH2:7][Br:9].Br[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:11][cH:10]1.[Mg:8]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][Mg:8][Br:9])[cH:10][cH:11]1 | BrCCBr.COc1ccc(Br)cc1.[Mg] | COc1ccc([CH2][Mg][Br])cc1 | null | null | null | C-C Coupling | OtherReaction | 9715e07751be3d7cadbe1fdc48e97bed4ac08db10902529fa702981c6f96e883 | 798737e906b6055cdcd851af3dddf5a764921f9651ccac6f32257884e0fa16b2 | c1ccccc1 | Br-C-[CH2;D2;+0:1]-[Br;H0;D1;+0:2].Br-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].[Mg;H0;D0;+0:8]>>[Br;H0;D1;+0:2]-[Mg;H0;D2;+0:8]-[CH2;D2;+0:1]-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7] | null | [] | 20 | CELSIUS | 10 | MINUTE | Magnesium (36 g, 1.5 mol), iodine (a few crystals) and THF (1 L) were heated under nitrogen, with stirring, at reflux for 15 min. The mixture was cooled to 20° C., stirring stopped, and 1,2-dibromoethane (2.5 ml) added. After an exothermic reaction was observed (a few min) stirring was restarted which was accompanied b... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide.Primary halide | Magnesium halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | null | 20 | 0.166667 | BrCCBr.COc1ccc(Br)cc1.[Mg]>>COc1ccc([CH2][Mg][Br])cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6534326785de4d64a16466ff2b37b899 | C=O.Oc1cccnc1Br>>OCc1ccc(O)c(Br)n1 | [OH-].[K+].BrC1=NC=CC=C1O.[Na].C=O>>BrC1=NC(=CC=C1O)CO | [O:1]=[CH2:2].[cH:3]1[cH:4][cH:5][c:6]([OH:7])[c:8]([Br:9])[n:10]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[c:8]([Br:9])[n:10]1 | C=O.Oc1cccnc1Br | OCc1ccc(O)c(Br)n1 | null | null | C(C)(=O)O.O | C-C Coupling | OtherReaction | e828e08512136a1006e7ed8edf3ea1a358c5687d4ea7b00d12d245f1aeb515aa | 4396295d899f5d4f5de2e844a80fc7d194b4da158f49df3d2717206b401b59bd | c1ccncc1 | [CH2;D1;+0:1]=[O;H0;D1;+0:2].[c:3]:[c:4]:[cH;D2;+0:5]:[#7;a:6]:[c:7]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c;H0;D3;+0:5](:[#7;a:6]:[c:7]):[c:4]:[c:3] | null | [] | null | null | 2 | HOUR | Potassium hydroxide (85% assay, 113.8 g, 1.73 mol) was dissolved in distilled water (750 ml) and to the solution was added 2-bromo-3-hydroxypyridine (300 g, 1.72 mol), ethylenediaminetetraaeetic acid sodium salt (2 mol %, 13.1 g, 0.034 mol) and formalin (37-41% w/v 470 ml, 5.95 mol). The stirred mixture was heated at 9... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde | Primary alcohol | c1ccncc1 | c1ccncc1 | c1ccncc1 | null | C(C)(=O)O.O | null | 2 | C=O.Oc1cccnc1Br>C(C)(=O)O.O>OCc1ccc(O)c(Br)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-518c5ae80b704ac1999ffc9853c652ad | C=CC(=O)OC(C)(C)C.COc1ccc(CCCCCCCCOc2ccc(CO)nc2Br)cc1>>COc1ccc(CCCCCCCCOc2ccc(CO)nc2C=CC(=O)OC(C)(C)C)cc1 | BrC1=NC(=CC=C1OCCCCCCCCC1=CC=C(C=C1)OC)CO.C(C)(=O)[O-].[K+].C(C=C)(=O)OC(C)(C)C.CCOCC>>OCC1=CC=C(C(=N1)C=CC(=O)OC(C)(C)C)OCCCCCCCCC1=CC=C(C=C1)OC | [CH2:24]=[CH:25][C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32].Br[c:23]1[c:16]([O:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:34][cH:33]2)[cH:17][cH:18][c:19]([CH2:20][OH:21])[n:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH2:9][CH2:10][... | C=CC(=O)OC(C)(C)C.COc1ccc(CCCCCCCCOc2ccc(CO)nc2Br)cc1 | COc1ccc(CCCCCCCCOc2ccc(CO)nc2C=CC(=O)OC(C)(C)C)cc1 | null | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | ClCCl.CN(C)C=O.O | C-C Coupling | Heck terminal vinyl | 6ff9a103c54245e6fd54f5e5a1a2869a152f70eb90c7b0a9e978953fb523505e | 4b186811a4930853b446d93d9faa39b267bddb9ce0b8021bda5c5a3b2bc69f0b | c1ccc(CCCCCCCCOc2cccnc2)cc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[#8:5]):[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[#8:11]-[C:12](=[O;D1;H0:13])-[C:14]=[CH2;D1;+0:15]>>[#8:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[CH;D2;+0:15]=[C:14]-[C:12](=[O;D1;H0:13])-[#8:11]-[C:8](-[C;D1;H3:7])(-[C;D1;H3:9])-[C;D1;H3:10]):[#7;a:2]:[c:3] | null | [] | 120 | CELSIUS | null | null | To a solution of 2-bromo-6-hydroxymethyl-[8(4-methoxyphenyl)octyloxy]pyridine (5.00 g, 11.8 mmol) in DMF (22.8 ml) and water (1.2 ml) were added potassium acetate (3.00 g, 30.6 mmol), tetra-n-butylammonium iodide (4.36 g, 11.8 mmol), bis(triphenylphosphine)palladium dichloride (0.33 g, 0.47 mmol) and t-butyl acrylate (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl | null | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | HBr | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.ClCCl.CN(C)C=O.O | 120 | null | C=CC(=O)OC(C)(C)C.COc1ccc(CCCCCCCCOc2ccc(CO)nc2Br)cc1>[I-].C(CCC)[N+](CCCC)(CCCC)CCCC.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.ClCCl.CN(C)C=O.O>COc1ccc(CCCCCCCCOc2ccc(CO)nc2C=CC(=O)OC(C)(C)C)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d167806c04b646d4b1c49664d0f6f7f3 | C=CC(=O)[O-].COc1ccc(CCCCCCCCOc2ccc(CO)nc2Br)cc1>>COc1ccc(CCCCCCCCOc2ccc(CO)nc2C=CC(=O)O)cc1 | C(C=C)(=O)[O-].[K+].BrC1=NC(=CC=C1OCCCCCCCCC1=CC=C(C=C1)OC)CO.C(C)(=O)[O-].[K+].C(C=C)(=O)[O-].[K+].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>OCC1=CC=C(C(=N1)C=CC(=O)O)OCCCCCCCCC1=CC=C(C=C1)OC | [CH2:24]=[CH:25][C:26](=[O:27])[O-:28].Br[c:23]1[c:16]([O:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:30][cH:29]2)[cH:17][cH:18][c:19]([CH2:20][OH:21])[n:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O... | C=CC(=O)[O-].COc1ccc(CCCCCCCCOc2ccc(CO)nc2Br)cc1 | COc1ccc(CCCCCCCCOc2ccc(CO)nc2C=CC(=O)O)cc1 | null | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC.[Pd](Cl)Cl | CN(C)C=O.O | C-C Coupling | OtherReaction | 3b41ec1889793db9e086d930ee817d7e17590040116fe3ea8390760f5b59a649 | 96c1c356cfda99239d83270c8639c030c1984d01ddd836a1f89bde5e602ad450 | c1ccc(CCCCCCCCOc2cccnc2)cc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[#8:5]):[c:6].[CH2;D1;+0:7]=[C:8]-[C:9](-[O-;H0;D1:10])=[O;D1;H0:11]>>[#8:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[CH;D2;+0:7]=[C:8]-[C:9](=[O;D1;H0:11])-[OH;D1;+0:10]):[#7;a:2]:[c:3] | null | [] | 120 | CELSIUS | null | null | To a solution of 2-bromo-6-hydroxymethyl-[8(4-methoxyphenyl)octyloxy]pyridine (5.00 g, 11.8 mmol) in DMF (22.8 ml) and water (1.2 ml) were added potassium acetate (2.91 g, 29.7 mmol), tetra-n-butylammonium iodide (4.37 g, 11.8 mmol); triphenylphosphine (0.245 g, 0.94 mmol), palladium chloride (83 mg, 0.47 mmol) and pot... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl | Carboxylic acid | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | Br- | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC.[Pd](Cl)Cl.CN(C)C=O.O | 120 | null | C=CC(=O)[O-].COc1ccc(CCCCCCCCOc2ccc(CO)nc2Br)cc1>[I-].C(CCC)[N+](CCCC)(CCCC)CCCC.[Pd](Cl)Cl.CN(C)C=O.O>COc1ccc(CCCCCCCCOc2ccc(CO)nc2C=CC(=O)O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-daea2679130c4e96a69efc91647c4537 | C=CC(=O)OCC.Cc1ccc(O)c(I)n1>>C=C(C(=O)OCC)c1nc(C)ccc1O | OC=1C(=NC(=CC1)C)I.C(C)(=O)[O-].[K+].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C=C)(=O)OCC>>OC=1C(=NC(=CC1)C)C(C(=O)OCC)=C | [CH2:1]=[CH:2][C:3](=[O:4])[O:5][CH2:6][CH3:7].I[c:8]1[n:9][c:10]([CH3:11])[cH:12][cH:13][c:14]1[OH:15]>>[CH2:1]=[C:2]([C:3](=[O:4])[O:5][CH2:6][CH3:7])[c:8]1[n:9][c:10]([CH3:11])[cH:12][cH:13][c:14]1[OH:15] | C=CC(=O)OCC.Cc1ccc(O)c(I)n1 | C=C(C(=O)OCC)c1nc(C)ccc1O | null | [Pd](Cl)Cl | CN(C)C=O.O | C-C Coupling | OtherReaction | 8d3cfa690cead9dcdb5f0a1f56e2ac08c5de55d1454f6c77dc7ae2812b1acf3d | 0148cae362ae1ae42dbb9a3b681759839c81f4c02b0942bce45e45dd2b0b9c70 | c1ccncc1 | I-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[O;D1;H1:5]):[c:6].[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH;D2;+0:11]=[C;D1;H2:12]>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[C;H0;D3;+0:11](=[C;D1;H2:12])-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[O;D1;H1:5]):[c:6] | null | [] | 120 | CELSIUS | null | null | To a solution of 3-hydroxy-2-iodo-6-methylpyridine (1.175 g, 5.0 mmol) in DMF (9.5 ml) and water (0.5 ml) were added potassium acetate (1.23 g, 12.5 mmol), triphenylphosphine (105 mg, 0.40 mmol), palladium chloride (36 mg, 0.20 mmol) and ethyl acrylate (1.63 ml, 1.50 g, 15.0 mmol). The mixture was placed under nitrogen... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester | Ester.Vinyl | c1ccncc1 | c1ccncc1 | c1ccncc1 | HI | [Pd](Cl)Cl.CN(C)C=O.O | 120 | null | C=CC(=O)OCC.Cc1ccc(O)c(I)n1>[Pd](Cl)Cl.CN(C)C=O.O>C=C(C(=O)OCC)c1nc(C)ccc1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-33f5c2c61cec497c9cae12b9bafc104f | C=CC(=O)OCC.OCc1ccc(O)c(I)n1>>CCOC(=O)C=Cc1nc(CO)ccc1O | OC=1C(=NC(=CC1)CO)I.C(C)(=O)[O-].[K+].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C=C)(=O)OCC>>OC=1C(=NC(=CC1)CO)C=CC(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH2:7].I[c:8]1[n:9][c:10]([CH2:11][OH:12])[cH:13][cH:14][c:15]1[OH:16]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH:7][c:8]1[n:9][c:10]([CH2:11][OH:12])[cH:13][cH:14][c:15]1[OH:16] | C=CC(=O)OCC.OCc1ccc(O)c(I)n1 | CCOC(=O)C=Cc1nc(CO)ccc1O | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | CN(C)C=O.O | C-C Coupling | Heck terminal vinyl | 6ff9a103c54245e6fd54f5e5a1a2869a152f70eb90c7b0a9e978953fb523505e | 4b186811a4930853b446d93d9faa39b267bddb9ce0b8021bda5c5a3b2bc69f0b | c1ccncc1 | I-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[O;D1;H1:5]):[c:6].[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[C:11]=[CH2;D1;+0:12]>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[C:11]=[CH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[O;D1;H1:5]):[c:6] | null | [] | 120 | CELSIUS | null | null | To a solution of 3-hydroxy-6-hydroxymethyl-2-iodopyridine (708 mg, 2.82 mmol) in DMF (5.7 ml) and water (0.3 ml) were added potassium acetate (0.74 g, 7.5 mmol), triphenylphosphine (63 mg, 0.24 mmol), ethyl acrylate (0.98 ml, 0.90 g, 9.0 mmol) and palladium acetate (27 mg, 0.12 mmol). The mixture was placed under nitro... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl | null | c1ccncc1 | c1ccncc1 | c1ccncc1 | HI | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CN(C)C=O.O | 120 | null | C=CC(=O)OCC.OCc1ccc(O)c(I)n1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CN(C)C=O.O>CCOC(=O)C=Cc1nc(CO)ccc1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7962bc1b7397448eac87976efef7cca2 | C=CC(=O)OCC.OCc1ccc(OCc2ccccc2)c(I)n1>>C=C(C(=O)OCC)c1nc(CO)ccc1OCc1ccccc1 | C(C1=CC=CC=C1)OC=1C(=NC(=CC1)CO)I.C(C)(=O)[O-].[K+].C(C=C)(=O)OCC>>C(C1=CC=CC=C1)OC=1C(=NC(=CC1)CO)C(C(=O)OCC)=C | [CH2:1]=[CH:2][C:3](=[O:4])[O:5][CH2:6][CH3:7].I[c:8]1[n:9][c:10]([CH2:11][OH:12])[cH:13][cH:14][c:15]1[O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH2:1]=[C:2]([C:3](=[O:4])[O:5][CH2:6][CH3:7])[c:8]1[n:9][c:10]([CH2:11][OH:12])[cH:13][cH:14][c:15]1[O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]... | C=CC(=O)OCC.OCc1ccc(OCc2ccccc2)c(I)n1 | C=C(C(=O)OCC)c1nc(CO)ccc1OCc1ccccc1 | null | null | CN(C)C=O.O | C-C Coupling | OtherReaction | 8d3cfa690cead9dcdb5f0a1f56e2ac08c5de55d1454f6c77dc7ae2812b1acf3d | 0148cae362ae1ae42dbb9a3b681759839c81f4c02b0942bce45e45dd2b0b9c70 | c1ccc(COc2cccnc2)cc1 | I-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[#8:5]):[c:6].[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH;D2;+0:11]=[C;D1;H2:12]>>[#8:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[C;H0;D3;+0:11](=[C;D1;H2:12])-[C:9](=[O;D1;H0:10])-[#8:8]-[C:7]):[#7;a:2]:[c:3] | 62 | [{"value": 62.0, "product": "C(C1=CC=CC=C1)OC=1C(=NC(=CC1)CO)C(C(=O)OCC)=C", "details": "PERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | To a solution of 3-benzyloxy-6-hydroxymethyl-2-iodopyridine (1.20 g, 3.50 mmol) in DMF (6.4 ml) and water (0.32 ml) were added potassium acetate (0.83 g, 8.5 mmol) palladium acetate (32 mg, 0.14 mmol) and ethyl acrylate (1.1 ml, 1.01 g, 10 mmol). The mixture was placed under nitrogen and stirred and heated at 120° C. f... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester | Ester.Vinyl | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HI | CN(C)C=O.O | 120 | null | C=CC(=O)OCC.OCc1ccc(OCc2ccccc2)c(I)n1>CN(C)C=O.O>C=C(C(=O)OCC)c1nc(CO)ccc1OCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-cbc402db79bd4ddea3a7284194868b01 | C=CC(=O)OCCCC.OCc1ccc(OCc2ccccc2)c(Br)n1>>C=C(C(=O)OCCCC)c1nc(CO)ccc1OCc1ccccc1 | BrC1=NC(=CC=C1OCC1=CC=CC=C1)CO.C(C)(=O)[O-].[K+].C(C=C)(=O)OCCCC>>C(C1=CC=CC=C1)OC=1C(=NC(=CC1)CO)C(C(=O)OCCCC)=C | [CH2:1]=[CH:2][C:3](=[O:4])[O:5][CH2:6][CH2:7][CH2:8][CH3:9].Br[c:10]1[n:11][c:12]([CH2:13][OH:14])[cH:15][cH:16][c:17]1[O:18][CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH2:1]=[C:2]([C:3](=[O:4])[O:5][CH2:6][CH2:7][CH2:8][CH3:9])[c:10]1[n:11][c:12]([CH2:13][OH:14])[cH:15][cH:16][c:17]1[O:18][CH2:19][c:20]1[c... | C=CC(=O)OCCCC.OCc1ccc(OCc2ccccc2)c(Br)n1 | C=C(C(=O)OCCCC)c1nc(CO)ccc1OCc1ccccc1 | null | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | CN(C)C=O.O | C-C Coupling | OtherReaction | 8d3cfa690cead9dcdb5f0a1f56e2ac08c5de55d1454f6c77dc7ae2812b1acf3d | 0148cae362ae1ae42dbb9a3b681759839c81f4c02b0942bce45e45dd2b0b9c70 | c1ccc(COc2cccnc2)cc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[#8:5]):[c:6].[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH;D2;+0:11]=[C;D1;H2:12]>>[#8:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[C;H0;D3;+0:11](=[C;D1;H2:12])-[C:9](=[O;D1;H0:10])-[#8:8]-[C:7]):[#7;a:2]:[c:3] | null | [] | 120 | CELSIUS | null | null | To a solution of 2-bromo-3-benzyloxy-6-hydroxymethylpyridine (2.94 g, 10.0 mmol) in DMF (19 ml) and water (1 ml) were added potassium acetate (2.45 g, 25.0 mmol), tetra-n-butylammonium iodide (3.69 g, 10.0 mmol), bis(triphenylphosphine)palladium dichloride (281 mg, 0.4 mmol) and n-butyl acrylate (4.31 ml, 3.84 g, 30 mm... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester | Ester.Vinyl | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HBr | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C)C=O.O | 120 | null | C=CC(=O)OCCCC.OCc1ccc(OCc2ccccc2)c(Br)n1>[I-].C(CCC)[N+](CCCC)(CCCC)CCCC.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C)C=O.O>C=C(C(=O)OCCCC)c1nc(CO)ccc1OCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a748f251ca1d423aa7e17eaf3d09ac7f | C=CC(=O)OC.OCc1ccc(OCc2ccccc2)c(Br)n1>>C=C(C(=O)OC)c1nc(CO)ccc1OCc1ccccc1 | BrC1=NC(=CC=C1OCC1=CC=CC=C1)CO.C(C)(=O)[O-].[K+].C(C=C)(=O)OC>>C(C1=CC=CC=C1)OC=1C(=NC(=CC1)CO)C(C(=O)OC)=C | [CH2:1]=[CH:2][C:3](=[O:4])[O:5][CH3:6].Br[c:7]1[n:8][c:9]([CH2:10][OH:11])[cH:12][cH:13][c:14]1[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH2:1]=[C:2]([C:3](=[O:4])[O:5][CH3:6])[c:7]1[n:8][c:9]([CH2:10][OH:11])[cH:12][cH:13][c:14]1[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | C=CC(=O)OC.OCc1ccc(OCc2ccccc2)c(Br)n1 | C=C(C(=O)OC)c1nc(CO)ccc1OCc1ccccc1 | null | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | CN(C)C=O.O | C-C Coupling | OtherReaction | 8d3cfa690cead9dcdb5f0a1f56e2ac08c5de55d1454f6c77dc7ae2812b1acf3d | 0148cae362ae1ae42dbb9a3b681759839c81f4c02b0942bce45e45dd2b0b9c70 | c1ccc(COc2cccnc2)cc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[#8:5]):[c:6].[C;D1;H2:7]=[CH;D2;+0:8]-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12]>>[#8:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[C;H0;D3;+0:8](=[C;D1;H2:7])-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12]):[#7;a:2]:[c:3] | 84.1 | [{"value": 84.0, "product": "C(C1=CC=CC=C1)OC=1C(=NC(=CC1)CO)C(C(=O)OC)=C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.1, "product": "C(C1=CC=CC=C1)OC=1C(=NC(=CC1)CO)C(C(=O)OC)=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | To a solution of 2-bromo-3-benzyloxy-6-hydroxymethylpyridine (2.94 g, 10 mmol) in DMF (19 ml) and water (1 ml) were added potassium acetate (2.45 g, 10.0 mmol), tetra-n-butylammonium iodide (3.69 g. 10.0 mmol), bis(triphenyl-phosphine)palladium dichloride (281 mg, 0.4 mmol) and methyl acrylate (2.70 ml. 2.58 g, 30 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester | Ester.Vinyl | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HBr | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C)C=O.O | 120 | null | C=CC(=O)OC.OCc1ccc(OCc2ccccc2)c(Br)n1>[I-].C(CCC)[N+](CCCC)(CCCC)CCCC.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C)C=O.O>C=C(C(=O)OC)c1nc(CO)ccc1OCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-10d91779e086461aa563e2a37737f0b8 | CC(C)(C)OC(=O)NCC/C=C/c1cncnc1.CI>>CN(CC/C=C/c1cncnc1)C(=O)OC(C)(C)C | [H-].[Na+].C(C)(C)(C)OC(=O)NCC\C=C\C=1C=NC=NC1.IC.C(C)(C)NC(C)C>>CN(CC\C=C\C=1C=NC=NC1)C(=O)OC(C)(C)C | [NH:2]([CH2:3][CH2:4]/[CH:5]=[CH:6]/[c:7]1[cH:8][n:9][cH:10][n:11][cH:12]1)[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19].I[CH3:1]>>[CH3:1][N:2]([CH2:3][CH2:4]/[CH:5]=[CH:6]/[c:7]1[cH:8][n:9][cH:10][n:11][cH:12]1)[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19] | CC(C)(C)OC(=O)NCC/C=C/c1cncnc1.CI | CN(CC/C=C/c1cncnc1)C(=O)OC(C)(C)C | null | null | COCCOC.O.CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 29c841ae076cb6ee785aad2a4e3ce1a9b47357d7ad25657b8d9991b1347f5721 | c485eddcb40c5a0d396ffdb624041effa09ee4f5ca2ecce3fe13077cf65004ed | c1cncnc1 | I-[CH3;D1;+0:1].[C:2]=[C:3]/[C:4]-[C:5]-[NH;D2;+0:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C;D1;H3:13]>>[C:2]=[C:3]/[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH3;D1;+0:1])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C;D1;H3:13] | 76.1 | [{"value": 76.1, "product": "CN(CC\\C=C\\C=1C=NC=NC1)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | Under a nitrogen atmosphere, sodium hydride (0.78 g, 19.5 mmol, 60% dispersion in oil) was added to a stirring solution of IV (0.50 g, 2.0 mmol), 1,2-dimethyoxyethane (20 mL), DMF (25 mL), and a trace of diisopropylamine. The mixture was stirred at ambient temperature for 45 min, and a solution of iodomethane (2.59 g, ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester | Carbamic ester | null | null | c1cncnc1 | HI | COCCOC.O.CN(C)C=O | null | 0.75 | CC(C)(C)OC(=O)NCC/C=C/c1cncnc1.CI>COCCOC.O.CN(C)C=O>CN(CC/C=C/c1cncnc1)C(=O)OC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b463cdcceaba4202b2513724f75023cf | BrC(Br)(Br)Br.O=Cc1cccnc1>>BrC(Br)=Cc1cccnc1 | BrC(Br)(Br)Br.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N1=CC(=CC=C1)C=O>>BrC(=CC=1C=NC=CC1)Br | Br[C:2](Br)([Br:1])[Br:3].O=[CH:4][c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1>>[Br:1][C:2]([Br:3])=[CH:4][c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1 | BrC(Br)(Br)Br.O=Cc1cccnc1 | BrC(Br)=Cc1cccnc1 | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | b27e55226bb2edd452ae488b95081b2b03421ee27be6c3935dbea4c7a5eeb5f6 | 695d5d1b30a064e72a7d907baf677e910730421b6580cc4e59d378cd6f0be898 | c1ccncc1 | Br-[C;H0;D4;+0:1](-Br)(-[Br;D1;H0:2])-[Br;D1;H0:3].O=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9]>>[Br;D1;H0:2]-[C;H0;D3;+0:1](-[Br;D1;H0:3])=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9] | 70 | [{"value": 70.0, "product": "BrC(=CC=1C=NC=CC1)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.0, "product": "BrC(=CC=1C=NC=CC1)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | Tetrabromomethane (24.82 g, 0.747 mole) and triphenylphosphine (39.17 g, 0.149 mole) were stirred together in dry methylene chloride (100 mL) for 5 min. at 0° C. under a nitrogen atmosphere. To this mixture was added dropwise pyridine 3-carboxaldehyde (4 g, 0.0373 mole). The solution was then stirred for 45 min. at amb... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Aldehyde | Alkenyl halide.Alkenyl halide | null | null | c1ccncc1 | Br- | C(Cl)Cl | null | 0.75 | BrC(Br)(Br)Br.O=Cc1cccnc1>C(Cl)Cl>BrC(Br)=Cc1cccnc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-acfd98fbecaf4acda872324b5f557a19 | C=O.Cc1ccc(C2CCCN2)cn1>>Cc1ccc(C2CCCN2C)cn1 | CC1=NC=C(C=C1)C2CCCN2.C=O.[OH-].[Na+]>>CC1=NC=C(C=C1)C2CCCN2C | O=[CH2:11].[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]2[CH2:7][CH2:8][CH2:9][NH:10]2)[cH:12][n:13]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]2[CH2:7][CH2:8][CH2:9][N:10]2[CH3:11])[cH:12][n:13]1 | C=O.Cc1ccc(C2CCCN2)cn1 | Cc1ccc(C2CCCN2C)cn1 | null | null | C(=O)O | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Secondary Amine Methylation | 91bb2ea8aeb046c2c7c6bbf5485a7fce0a359aeb3adea3549d5b06757bc9a669 | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | c1cncc(C2CCCN2)c1 | O=[CH2;D1;+0:1].[#7;a:2]:[c:3]:[c:4]-[C:5]1-[C:6]-[C:7]-[C:8]-[NH;D2;+0:9]-1>>[#7;a:2]:[c:3]:[c:4]-[C:5]1-[C:6]-[C:7]-[C:8]-[N;H0;D3;+0:9]-1-[CH3;D1;+0:1] | 92 | [{"value": 92.0, "product": "CC1=NC=C(C=C1)C2CCCN2C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Into a round bottom flask was placed XVI (2.0 g), and formaldehyde (37% w/v in water, 20 mL) and formic acid (95-97% w/v, 45 mL), both a 0° C., were added. The mixture then was refluxed under nitrogen for 8 hr. The cooled reaction mixture was basified with aqueous sodium hydroxide (50% w/v) to pH 8-9, and the solution ... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccncc1.C1CC[NH]C1 | Other | C(=O)O | null | null | C=O.Cc1ccc(C2CCCN2)cn1>C(=O)O>Cc1ccc(C2CCCN2C)cn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-73e83470040446eba51ba941b5338013 | NCCc1ccc(O)c(O)c1.O=S(=O)(O)CCN1CCN(CCO)CC1.O=S(=O)(O)CCN1CCN(CCO)CC1>>CN1CCC[C@H]1c1cccnc1 | C1CN(CCN1CCO)CCS(=O)(=O)O.NCCC1=CC(O)=C(O)C=C1.C1CN(CCN1CCO)CCS(=O)(=O)O.NCCC1=CC(O)=C(O)C=C1>>N1=CC=CC(=C1)[C@H]1N(C)CCC1 | N[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10](O)c(O)[cH:12]1.O=S(=O)(O)CCN1CC[N:11](CCO)CC1.O=S(=O)(O)CCN1CC[N:2]([CH2:1]CO)[CH2:3][CH2:4]1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][C@H:6]1[c:7]1[cH:8][cH:9][cH:10][n:11][cH:12]1 | NCCc1ccc(O)c(O)c1.O=S(=O)(O)CCN1CCN(CCO)CC1.O=S(=O)(O)CCN1CCN(CCO)CC1 | CN1CCC[C@H]1c1cccnc1 | null | null | C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@]2([C@H]([C@@H]([C@H](O2)CO)O)O)CO)O)O)O)O | Heteroatom Alkylation and Arylation | OtherReaction | 19fc9a872b549396d811b42e2ef2bc61edfc6ad753a9b784038fcb2d26d8bd1b | 22424af31acac19f7bdb5717c7b71b423c8772246143962540fd1af6bf911444 | c1cncc([C@@H]2CCCN2)c1 | N-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[c;H0;D3;+0:6](-O):c(-O):[cH;D2;+0:7]:1.O-C-C-[N;H0;D3;+0:8]1-C-C-N(-C-C-S(-O)(=O)=O)-C-C-1.O-C-[CH2;D2;+0:9]-[N;H0;D3;+0:10]1-C-C-N(-C-C-S(-O)(=O)=O)-[CH2;D2;+0:11]-[C:12]-1>>[CH3;D1;+0:9]-[N;H0;D3;+0:10]1-[C:12]-[CH2;D2;+0:11]-[CH2;D2;+0:1]-[C@H;D3;+0:2]-1-[c:3]1:[c:4]... | null | [] | null | null | 10 | MINUTE | Dopamine release was measured by preparing synaptosomes from the striatal area of rat brain obtained from Sprague-Dawley rats generally according to the procedures set forth by Nagy et al., J. Neurochem., Vol. 43, pp. 1114-1123 (1984). Striata from 4 rats were homogenized in 2 ml of 0.32M sucrose buffered with 5 mM HEP... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary alcohol.Aromatic alcohol.Aromatic alcohol.Primary amine.Tertiary amine.Tertiary amine.Tertiary amine.Tertiary amine.Sulfonic acid.Sulfonic acid | Tertiary amine | c1ccccc1.C1CNCC[NH]1.C1CNCC[NH]1 | C1CC[NH]C1.c1ccncc1 | C1CC[NH]C1.c1ccncc1 | HO- | C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@]2([C@H]([C@@H]([C@H](O2)CO)O)O)CO)O)O)O)O | null | 0.166667 | NCCc1ccc(O)c(O)c1.O=S(=O)(O)CCN1CCN(CCO)CC1.O=S(=O)(O)CCN1CCN(CCO)CC1>C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@]2([C@H]([C@@H]([C@H](O2)CO)O)O)CO)O)O)O)O>CN1CCC[C@H]1c1cccnc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2efa0157f0794899ae4b9b6277f9cfd2 | COC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)c1ccccc1.O=CC(Cl)(Cl)Cl>>COC(=O)[C@@H]1OC(C(Cl)(Cl)Cl)N[C@H]1c1ccccc1 | C(C)(C)(C)OC(=O)N[C@H]([C@H](C(=O)OC)O)C1=CC=CC=C1.O=CC(Cl)(Cl)Cl.C1(=CC=C(C=C1)S(=O)(=O)[O-])C.[NH+]1=CC=CC=C1>>COC(=O)[C@H]1[C@@H](NC(O1)C(Cl)(Cl)Cl)C1=CC=CC=C1 | CC(C)(C)O[C:7](=O)[NH:12][C@H:13]([C@H:5]([C:3]([O:2][CH3:1])=[O:4])[OH:6])[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.O=C[C:8]([Cl:9])([Cl:10])[Cl:11]>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[O:6][CH:7]([C:8]([Cl:9])([Cl:10])[Cl:11])[NH:12][C@H:13]1[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | COC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)c1ccccc1.O=CC(Cl)(Cl)Cl | COC(=O)[C@@H]1OC(C(Cl)(Cl)Cl)N[C@H]1c1ccccc1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 875f311f15254ab0306d385b68a0217cd66c4ae0dba2b1f601a96620dbad3fb4 | 8f365cb6871fb0212098d3b154969febdc519bee26d88c8a0ee935c154eca887 | c1ccc([C@H]2COCN2)cc1 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=O)-[#7:2]-[C:3]-[C:4](-[OH;D1;+0:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C;D1;H3:9].O=C-[C;H0;D4;+0:10](-[Cl;D1;H0:11])(-[Cl;D1;H0:12])-[Cl;D1;H0:13]>>[C;D1;H3:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[C:4]1-[C:3]-[#7:2]-[CH;D3;+0:1](-[C;H0;D4;+0:10](-[Cl;D1;H0:11])(-[Cl;D1;H0:12])-[Cl;D1;H0:13])-[O;H0;D2;+0... | 91 | [{"value": 91.0, "product": "COC(=O)[C@H]1[C@@H](NC(O1)C(Cl)(Cl)Cl)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | null | null | A solution of 3.0 g of methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate, of 5 cm3 of chloral and of 0.05 g of pyridinium p-toluenesulphonate in 40 cm3 of anhydrous toluene is heated at reflux with distillation of the solvent. 15 cm3 of solvent are distilled and then 5 cm3 of chloral and 0.05 g o... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Aldehyde.Carbamic ester.Ether.Secondary alcohol.Boc | Trichloro group.Ether | null | C1COCN1 | C1COCN1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | 20 | null | COC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)c1ccccc1.O=CC(Cl)(Cl)Cl>C1(=CC=CC=C1)C>COC(=O)[C@@H]1OC(C(Cl)(Cl)Cl)N[C@H]1c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d735999e237040e79efd9e34aa9e36bf | CCOC(=O)CBr.CSC>>CCOC(=O)C[S+](C)C.[Br-] | BrCC(=O)OCC.CSC>>[Br-].C(=O)(OCC)C[S+](C)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][Br:10].[S:7]([CH3:8])[CH3:9]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][S+:7]([CH3:8])[CH3:9].[Br-:10] | CCOC(=O)CBr.CSC | CCOC(=O)C[S+](C)C.[Br-] | null | null | CC(=O)C | Functional Group Interconversion | OtherReaction | 330ba230541c446579322dd1f88c2db776aefe9bd80c8cf1780c2ef11bd721f7 | 7219c7e59d7b4e04c52ec17fd1785ce10066175f9fdee39a2b95a7cdf0cce07b | null | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[C;D1;H3:7]-[S;H0;D2;+0:8]-[C;D1;H3:9]>>[Br-;H0;D0:1].[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:2]-[S+;H0;D3:8](-[C;D1;H3:7])-[C;D1;H3:9] | null | [] | null | null | 3 | DAY | A solution of ethyl bromoacetate (265 g) and dimethyl sulfide (114 g) in acetone (500 mL) was stirred at room temperature. After three days, the title compound was isolated by filtration of the reaction mixture. Melting point 88°-90° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Monosulfide | Ester | null | null | null | null | CC(=O)C | null | 72 | CCOC(=O)CBr.CSC>CC(=O)C>CCOC(=O)C[S+](C)C.[Br-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8fef71afc98949c49bc84e25d6876698 | CCOC(=O)C[S+](C)C.O=C1C=CCC1>>CCOC(=O)C1C2CCC(=O)C21 | Cl.[Cl-].[Na+].N12CCCCCC2=NCCC1.[Br-].C(=O)(OCC)C[S+](C)C.C1(C=CCC1)=O>>O=C1C2C(C2CC1)C(=O)OCC | C[S+](C)[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[CH:7]1=[CH:12][C:10](=[O:11])[CH2:9][CH2:8]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH:7]2[CH2:8][CH2:9][C:10](=[O:11])[CH:12]12 | CCOC(=O)C[S+](C)C.O=C1C=CCC1 | CCOC(=O)C1C2CCC(=O)C21 | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 12efc71b43a52362bb5f8e0d3581ffe17688ff325d048d90483f02a1e254244b | 94c7364692188ef8ef531518cf74a9fca9728a2aa5d4b3e96a01bb7b82219171 | O=C1CCC2CC12 | C-[S+](-C)-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[O;D1;H0:6]=[C:7]1-[C:8]-[C:9]-[CH;D2;+0:10]=[CH;D2;+0:11]-1>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH;D3;+0:1]1-[CH;D3;+0:11]2-[C:7](=[O;D1;H0:6])-[C:8]-[C:9]-[CH;D3;+0:10]-2-1 | 68.3 | [{"value": 68.3, "product": "O=C1C2C(C2CC1)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A suspension of carboethoxymethyl dimethylsulfonium bromide (45.5 g) in toluene (350 mL) was treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (30.2 g). The resulting mixture was stirred at room temperature. After one hour, the reaction mixture was treated with 2-cyclopenten-1-one (19.57 g). After an additional 18 hours,... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ketone.Ester | C1=CCCC1 | C1CC2CC2C1 | C1CC2CC2C1 | Other | C1(=CC=CC=C1)C | null | 1 | CCOC(=O)C[S+](C)C.O=C1C=CCC1>C1(=CC=CC=C1)C>CCOC(=O)C1C2CCC(=O)C21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-07beb0ec388f43cd9ac71486ee726a73 | CCOC(=O)C1C2CCC(=O)C21>>O=C(O)C1C2CCC(=O)C21 | O=C1C2C(C2CC1)C(=O)OCC.Cl>>O=C1C2C(C2CC1)C(=O)O | CC[O:3][C:2](=[O:1])[CH:4]1[CH:5]2[CH2:6][CH2:7][C:8](=[O:9])[CH:10]12>>[O:1]=[C:2]([OH:3])[CH:4]1[CH:5]2[CH2:6][CH2:7][C:8](=[O:9])[CH:10]12 | CCOC(=O)C1C2CCC(=O)C21 | O=C(O)C1C2CCC(=O)C21 | null | null | [OH-].[Na+] | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1CCC2CC12 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | 2.5 | HOUR | A mixture of 60 g of ethyl 2-oxobicyclo[3.1.0]hexane-6-carboxylate and 300 ml of 1N sodium hydroxide was stirred at 25°-30° C. After 2.5 hours, concentrated hydrochloric acid was added to adjust the pH to 0.8-1.2. The resulting solution was extracted with ethyl acetate. The extracts were dried over magnesium sulfate, f... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC2CC2C1 | Other | [OH-].[Na+] | null | 2.5 | CCOC(=O)C1C2CCC(=O)C21>[OH-].[Na+]>O=C(O)C1C2CCC(=O)C21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8b32fa3382184901ae70790edf4034ba | CC(Br)C(=O)Br.CNc1cccc(OC)c1>>COc1cccc(N(C)C(=O)C(C)Br)c1 | CNC=1C=C(OC)C=CC1.C(C)N(CC)CC.C1(=CC=CC=C1)C.BrC(C(=O)Br)C>>BrC(C(=O)N(C)C1=CC(=CC=C1)OC)C | Br[C:10](=[O:11])[CH:12]([CH3:13])[Br:14].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][CH3:9])[cH:15]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([N:8]([CH3:9])[C:10](=[O:11])[CH:12]([CH3:13])[Br:14])[cH:15]1 | CC(Br)C(=O)Br.CNc1cccc(OC)c1 | COc1cccc(N(C)C(=O)C(C)Br)c1 | null | null | O | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccccc1 | Br-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[Br;D1;H0:4])-[C;D1;H3:5].[C;D1;H3:6]-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[Br;D1;H0:4]-[C:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:7](-[C;D1;H3:6])-[c:8](:[c:9]):[c:10] | null | [] | null | null | 8 | HOUR | A solution of N-methyl-m-anisidine (265 g), triethylamine (269 ml) and toluene (550 ml) was stirred at 0° C. as 2-bromopropionyl bromide (202.6 ml) was added dropwise. The mixture was mechanically stirred overnight at room temperature. Water was added to the reaction and the aqueous layer was collected and extracted wi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1 | HBr | O | null | 8 | CC(Br)C(=O)Br.CNc1cccc(OC)c1>O>COc1cccc(N(C)C(=O)C(C)Br)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-81f17a5f0c63408184ecd6ae2c164668 | COc1cc2c(cc1Br)[C@]1(C)CCN(C)[C@@H]1N2C>>CN1CC[C@@]2(C)c3cc(Br)c(O)cc3N(C)[C@@H]12 | BrC=1C=C2[C@]3([C@@H](N(C2=CC1OC)C)N(CC3)C)C.B(Br)(Br)Br>>BrC=1C=C2[C@]3([C@@H](N(C2=CC1O)C)N(CC3)C)C | C[O:12][c:11]1[c:9]([Br:10])[cH:8][c:7]2[c:14]([cH:13]1)[N:15]([CH3:16])[C@H:17]1[N:2]([CH3:1])[CH2:3][CH2:4][C@@:5]21[CH3:6]>>[CH3:1][N:2]1[CH2:3][CH2:4][C@@:5]2([CH3:6])[c:7]3[cH:8][c:9]([Br:10])[c:11]([OH:12])[cH:13][c:14]3[N:15]([CH3:16])[C@@H:17]12 | COc1cc2c(cc1Br)[C@]1(C)CCN(C)[C@@H]1N2C | CN1CC[C@@]2(C)c3cc(Br)c(O)cc3N(C)[C@@H]12 | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2c(c1)N[C@H]1NCCC21 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 8 | HOUR | cis-(±)-5-Bromo-1,2,3,3a,8,8a-hexahydro-6-methoxy- 1,3a,8-trimethyl-pyrrolo[2,3-b]indole (11 g) was dissolved in dry DCM (200 ml) and added dropwise at 0° C. to a stirred solution of BBr3 in DCM (300 ml). The mixture was warmed to room temperature and stirred overnight under nitrogen. The mixture was quenched with aq. ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2c(c1)[NH][C@H]1[NH]CC[C@@H]21 | Other | C(Cl)Cl | null | 8 | COc1cc2c(cc1Br)[C@]1(C)CCN(C)[C@@H]1N2C>C(Cl)Cl>CN1CC[C@@]2(C)c3cc(Br)c(O)cc3N(C)[C@@H]12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0f8c43802c60460ab93e17f76623a594 | CC1C(=O)N(C)c2cccc(O)c21.COS(=O)(=O)OC>>COc1cccc2c1C(C)C(=O)N2C | OC1=C2C(C(N(C2=CC=C1)C)=O)C.C([O-])([O-])=O.[K+].[K+].COS(=O)(=O)OC>>COC1=C2C(C(N(C2=CC=C1)C)=O)C | [OH:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[CH:9]([CH3:10])[C:11](=[O:12])[N:13]2[CH3:14].COS(=O)(=O)O[CH3:1]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[CH:9]([CH3:10])[C:11](=[O:12])[N:13]2[CH3:14] | CC1C(=O)N(C)c2cccc(O)c21.COS(=O)(=O)OC | COc1cccc2c1C(C)C(=O)N2C | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Methylation of OH with DMS | b8b041187bac58376aae824630608e7deb49a01db3d652291f8b379c10d4e434 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | O=C1Cc2ccccc2N1 | C-O-S(=O)(=O)-O-[CH3;D1;+0:1].[OH;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:2]-[c:3](:[c:4]):[c:5] | 86.2 | [{"value": 86.2, "product": "COC1=C2C(C(N(C2=CC=C1)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A slurry of 1,3-dihydro-4-hydroxy-1,3-dimethyl-2H-indol-2-one (50 g), milled potassium carbonate (60.1 g) and HPLC grade acetone (400 ml) was mechanically stirred at room temperature as dimethylsulfate (41.4 ml) was added dropwise. The addition funnel was replaced with a condenser and the slurry was refluxed for 18 hou... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | null | null | c1ccc2c(c1)CC[NH]2 | HO- | CC(=O)C | null | null | CC1C(=O)N(C)c2cccc(O)c21.COS(=O)(=O)OC>CC(=O)C>COc1cccc2c1C(C)C(=O)N2C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-cb9d1bc99b9b4ab18c65744a87225d92 | CC(N=C=O)c1ccccc1.CN1CC[C@@]2(C)c3c(O)cccc3N(C)[C@@H]12>>C[C@@H](NC(=O)Oc1cccc2c1[C@@]1(C)CCN(C)[C@H]1N2C)c1ccccc1 | CN1CC[C@@]2([C@H]1N(C=1C=CC=C(C21)O)C)C.C1CCC2=NCCCN2CC1.CC(C1=CC=CC=C1)N=C=O>>C[C@H](C1=CC=CC=C1)NC(OC1=C2[C@@]3([C@H](N(C2=CC=C1)C)N(CC3)C)C)=O | [CH3:1][CH:2]([N:3]=[C:4]=[O:5])[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1.[OH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[C@:13]1([CH3:14])[CH2:15][CH2:16][N:17]([CH3:18])[C@@H:19]1[N:20]2[CH3:21]>>[CH3:1][C@@H:2]([NH:3][C:4](=[O:5])[O:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[C@@:13]1([CH3:14])[CH2:15][CH2:16][N:17]([... | CC(N=C=O)c1ccccc1.CN1CC[C@@]2(C)c3c(O)cccc3N(C)[C@@H]12 | C[C@@H](NC(=O)Oc1cccc2c1[C@@]1(C)CCN(C)[C@H]1N2C)c1ccccc1 | null | null | C1CCOC1 | Protection | OtherReaction | 1cd060f96f1d4acffc14539274a5df6a214938373877da5ea80bcb2e30d74918 | 55864cdc06e9526eaed7216ed2cc57ef652f1657070e16ae5b01f42ad254cf4b | O=C(NCc1ccccc1)Oc1cccc2c1C1CCN[C@H]1N2 | [C;D1;H3:1]-[CH;D3;+0:2](-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5])-[c:6](:[c:7]):[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C;D1;H3:1]-[C@@H;D3;+0:2](-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12])-[c:6](:[c:7]):[c:8] | null | [] | null | null | 8 | HOUR | cis-(±)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo [2,3-b]indol-4-ol (2g) was dissolved in degassed THF (200 ml). DBU (0.8 ml) was added to the mixture followed by R-(+)-α-methylbenzyl isocyanate (2 g). The reaction was stirred at room temperature overnight under nitrogen. The solvent was evaporated under reduced ... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Aromatic alcohol | Carbamic ester | null | null | c1ccc2c(c1)[NH][C@@H]1[NH]CC[C@H]21.c1ccccc1 | null | C1CCOC1 | null | 8 | CC(N=C=O)c1ccccc1.CN1CC[C@@]2(C)c3c(O)cccc3N(C)[C@@H]12>C1CCOC1>C[C@@H](NC(=O)Oc1cccc2c1[C@@]1(C)CCN(C)[C@H]1N2C)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-157fb9c3937847cf98e7bf4bb5a1bfb6 | CC(C)(C)C(=O)OCCl.CC(C)CN1C(=O)[C@@H](CC(=O)O)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21>>CC(C)CN1C(=O)[C@@H](CC(=O)OCOC(=O)C(C)(C)C)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 | ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)C)=O)CC(=O)O)C2=C(C=CC=C2)Cl)C1.C(C(C)(C)C)(=O)OCCl.C(C(C)C)N(CC(C)C)CC.O>>C(C(C)(C)C)(=O)OCOC(C[C@@H]1C(N(C2=C([C@H](O1)C1=C(C=CC=C1)Cl)C=C(C=C2)Cl)CC(C)C)=O)=O | Cl[CH2:13][O:14][C:15](=[O:16])[C:17]([CH3:18])([CH3:19])[CH3:20].[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[C@@H:8]([CH2:9][C:10](=[O:11])[OH:12])[O:21][C@H:22]([c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]2[Cl:29])[c:30]2[cH:31][c:32]([Cl:33])[cH:34][cH:35][c:36]21>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[... | CC(C)(C)C(=O)OCCl.CC(C)CN1C(=O)[C@@H](CC(=O)O)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 | CC(C)CN1C(=O)[C@@H](CC(=O)OCOC(=O)C(C)(C)C)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | d0f2e7dd04291aff91491624f6ba09bd6ae2852adc109edeabfddd534d9ccfd8 | ebb133741743004d799d6738504ddfd5b4a53248a4f85602c0fff1c33566ad58 | O=C1CO[C@H](c2ccccc2)c2ccccc2N1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5].[C:6]-[C:7](=[O;D1;H0:8])-[OH;D1;+0:9]>>[C:4]-[C:3](=[O;D1;H0:5])-[#8:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-[C:7](-[C:6])=[O;D1;H0:8] | null | [] | null | null | 8 | HOUR | In N,N-dimethylformamide (10 ml) was dissolved trans- 7-chloro-5-(2-chlorophenyl)-1-isobutyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid (0.5 g) obtained in Example 2. To the solution were added pivaloyloxymethyl chloride (0.43 ml), N,N-diisobutyl ethylamine (0.52 ml) and KI (0.2 g). The mixture was stirre... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester.Ester | null | null | c1ccccc1.c1ccc2c(c1)COCC[NH]2 | HCl | CN(C=O)C.C(C)(=O)OCC | null | 8 | CC(C)(C)C(=O)OCCl.CC(C)CN1C(=O)[C@@H](CC(=O)O)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21>CN(C=O)C.C(C)(=O)OCC>CC(C)CN1C(=O)[C@@H](CC(=O)OCOC(=O)C(C)(C)C)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8208d819f879448fbecf7d2aa5f1ad04 | COc1ccc(C=O)c(OC)c1.Nc1ccc(Cl)cc1C(O)c1ccccc1Cl>>COc1ccc(CNc2ccc(Cl)cc2C(O)c2ccccc2Cl)c(OC)c1 | O.NC1=C(C(C2=C(C=CC=C2)Cl)O)C=C(C=C1)Cl.COC1=C(C=O)C=CC(=C1)OC.[BH4-].[Na+]>>ClC=1C=CC(=C(C(C2=C(C=CC=C2)Cl)O)C1)NCC1=C(C=C(C=C1)OC)OC | O=[CH:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:28][c:25]1[O:26][CH3:27].[NH2:8][c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]1[CH:16]([OH:17])[c:18]1[cH:19][cH:20][cH:21][cH:22][c:23]1[Cl:24]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH:8][c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]2[CH:16]([OH:17])[c:18]2[c... | COc1ccc(C=O)c(OC)c1.Nc1ccc(Cl)cc1C(O)c1ccccc1Cl | COc1ccc(CNc2ccc(Cl)cc2C(O)c2ccccc2Cl)c(OC)c1 | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(CNc2ccccc2Cc2ccccc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[NH;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | 96.1 | [{"value": 96.1, "product": "ClC=1C=CC(=C(C(C2=C(C=CC=C2)Cl)O)C1)NCC1=C(C=C(C=C1)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 2-amino-5-chloro-α-(2-chloro phenyl)benzyl alcohol (5.0 g) and 2,4-dimethoxy benzaldehyde (3.72 g) in acetic acid (50 ml) was added, under ice-cooling, sodium borohydride (0.94 g). The mixture was stirred for one hour at room temperature, which was poured into water (200 ml), followed by extraction wit... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | Other | C(C)(=O)O | null | 1 | COc1ccc(C=O)c(OC)c1.Nc1ccc(Cl)cc1C(O)c1ccccc1Cl>C(C)(=O)O>COc1ccc(CNc2ccc(Cl)cc2C(O)c2ccccc2Cl)c(OC)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c2d7b50a1bd84d1e8cef8cf871d36f05 | O=C1CCC(C(=O)O)O1.O=S(Cl)Cl>>O=C1CCC(C(=O)Cl)O1 | O=C1CCC(O1)C(=O)O.S(=O)(Cl)Cl>>O=C1CCC(O1)C(=O)Cl | O[C:6]([CH:5]1[CH2:4][CH2:3][C:2](=[O:1])[O:9]1)=[O:7].O=S(Cl)[Cl:8]>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([C:6](=[O:7])[Cl:8])[O:9]1 | O=C1CCC(C(=O)O)O1.O=S(Cl)Cl | O=C1CCC(C(=O)Cl)O1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | O=C1CCCO1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4](-[C:5])-[#8:6]-[C:7]=[O;D1;H0:8]>>[C:5]-[C:4](-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3])-[#8:6]-[C:7]=[O;D1;H0:8] | null | [] | null | null | null | null | A mixture of 4.9 g of 5-oxotetrahydrofuran-2-carboxylic acid and 5.5 ml of thionyl chloride was subjected to reflux for 2 hours. Thionyl chloride was then distilled off under reduced pressure to leave 5-oxotetrahydrofuran-2-carbonyl chloride. This product was mixed with 5.0 g of 2-aminobenzophenone, 200 ml of ethyl ace... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | C1CCOC1 | HCl | null | null | null | O=C1CCC(C(=O)O)O1.O=S(Cl)Cl>>O=C1CCC(C(=O)Cl)O1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-947d3e4afae94a0b8dd4f97535b58d90 | Nc1ccccc1C(=O)c1ccccc1.O=C([O-])O>>O=C1CCC(C(=O)Nc2ccccc2C(=O)c2ccccc2)O1 | NC1=C(C(=O)C2=CC=CC=C2)C=CC=C1.C(O)([O-])=O.[Na+]>>O=C1CCC(O1)C(=O)NC1=C(C(=O)C2=CC=CC=C2)C=CC=C1 | [cH:2]1[c:17]([C:15]([c:14]2[c:9]([NH2:8])[cH:10][cH:11][cH:12][cH:13]2)=[O:16])[cH:18][cH:19][cH:20][cH:21]1.[O-:1][C:6](=[O:7])[OH:23]>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[C:15](=[O:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[O:23]1 | Nc1ccccc1C(=O)c1ccccc1.O=C([O-])O | O=C1CCC(C(=O)Nc2ccccc2C(=O)c2ccccc2)O1 | null | null | C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | 3b8ba0f8d519b260eb86a1b85cbd2a09fe48860e12a159295ca3a0782b453820 | 8ce2a5a806393bd18c953b6c97fbcdd6719072ce11d36a47b3c99f1b34ed4c0a | O=C1CCC(C(=O)Nc2ccccc2C(=O)c2ccccc2)O1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[c:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:1.[O-;H0;D1:13]-[C;H0;D3;+0:14](=[O;D1;H0:15])-[OH;D1;+0:16]>>[O;D1;H0:6]=[C:5](-[c:4]:[c:2](-[NH;D2;+0:1]-[C;H0;D3;+0:14](=[O;D1;H0:15])-[C:17]1-[C:18]-[C:19]-[C;H0;D3;+0:12](=[O;H0;D1;+0:13])-[O;H0;D2;... | null | [] | null | null | 1 | HOUR | A mixture of 4.9 g of 5-oxotetrahydrofuran-2-carboxylic acid and 5.5 ml of thionyl chloride was subjected to reflux for 2 hours. Thionyl chloride was then distilled off under reduced pressure to leave 5-oxotetrahydrofuran-2-carbonyl chloride. This product was mixed with 5.0 g of 2-aminobenzophenone, 200 ml of ethyl ace... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Acid.Ketone.Primary amine | Ketone.Ester.Secondary amide | c1ccccc1 | C1CCOC1.c1ccccc1 | C1CCOC1.c1ccccc1.c1ccccc1 | null | C(C)(=O)OCC | null | 1 | Nc1ccccc1C(=O)c1ccccc1.O=C([O-])O>C(C)(=O)OCC>O=C1CCC(C(=O)Nc2ccccc2C(=O)c2ccccc2)O1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b0c5b510b8454987be8e23400859a420 | Nc1ccc(Cl)cc1C(=O)c1ccccc1Cl.O=C1CCC(C(=O)Cl)O1>>O=C1CCC(C(=O)Nc2ccc(Cl)cc2C(=O)c2ccccc2Cl)O1 | NC1=C(C(=O)C2=C(C=CC=C2)Cl)C=C(C=C1)Cl.O=C1CCC(O1)C(=O)Cl>>ClC1=C(C=CC=C1)C(C1=C(C=CC(=C1)Cl)NC(=O)C1OC(CC1)=O)=O | [NH2:8][c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]1[C:16](=[O:17])[c:18]1[cH:19][cH:20][cH:21][cH:22][c:23]1[Cl:24].Cl[C:6]([CH:5]1[CH2:4][CH2:3][C:2](=[O:1])[O:25]1)=[O:7]>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]2[C:16](=[O:17])[c:18]2[cH:19][cH:20][cH:... | Nc1ccc(Cl)cc1C(=O)c1ccccc1Cl.O=C1CCC(C(=O)Cl)O1 | O=C1CCC(C(=O)Nc2ccc(Cl)cc2C(=O)c2ccccc2Cl)O1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(C(=O)Nc2ccccc2C(=O)c2ccccc2)O1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#8:5]-[C:6]=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]-[C:12]=[O;D1;H0:13]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]-[C:12]=[O;D1;H0:13])-[#8:5]-[C:6]=[O;D1;H0:7] | null | [] | null | null | null | null | In substantially the same manner as in Example 8 (1), 15 g of 2-amino-2',5-dichlorobenzophenone was allowed to react with 5-oxotetrahydrofuran-2-carbonyl chloride to afford 18.1 g of 2',5-dichloro-2-(5-oxotetrahydrofuran-2-carbonyl) aminobenzophenone, m.p. 170° C.-173° C.
Conditions: See reaction.notes.procedure_detail... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCOC1.c1ccccc1.c1ccccc1 | HCl | null | null | null | Nc1ccc(Cl)cc1C(=O)c1ccccc1Cl.O=C1CCC(C(=O)Cl)O1>>O=C1CCC(C(=O)Nc2ccc(Cl)cc2C(=O)c2ccccc2Cl)O1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9e9ed99cddf843adaf7a03857e42c160 | COc1ccc(C(=O)c2ccccc2N)cc1.O=C1CCC(C(=O)Cl)O1>>COc1ccc(C(=O)c2ccccc2NC(=O)C2CCC(=O)O2)cc1 | NC1=C(C(=O)C2=CC=C(C=C2)OC)C=CC=C1.O=C1CCC(O1)C(=O)Cl>>COC1=CC=C(C=C1)C(C1=C(C=CC=C1)NC(=O)C1OC(CC1)=O)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[NH2:15])[cH:24][cH:25]1.Cl[C:16](=[O:17])[CH:18]1[CH2:19][CH2:20][C:21](=[O:22])[O:23]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[NH:15][C:16](=[O:17])[CH:18]2[CH2:19][CH2:20][C:2... | COc1ccc(C(=O)c2ccccc2N)cc1.O=C1CCC(C(=O)Cl)O1 | COc1ccc(C(=O)c2ccccc2NC(=O)C2CCC(=O)O2)cc1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CCC(C(=O)Nc2ccccc2C(=O)c2ccccc2)O1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#8:5]-[C:6]=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]-[C:12]=[O;D1;H0:13]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]-[C:12]=[O;D1;H0:13])-[#8:5]-[C:6]=[O;D1;H0:7] | null | [] | null | null | null | null | In substantially the same manner as in Example 8 (1), 8 g of 2-amino-4'-methoxybenzophenone was allowed to react with 5-oxotetrahydrofuran-2-carbonyl chloride to give 12 g of 4'-methoxy-2-(5-oxotetrahydrofuran-2-carbonyl)aminobenzophenone as an oily product.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.C1CCOC1 | HCl | null | null | null | COc1ccc(C(=O)c2ccccc2N)cc1.O=C1CCC(C(=O)Cl)O1>>COc1ccc(C(=O)c2ccccc2NC(=O)C2CCC(=O)O2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9645ae5ef13440c58b9e8e3877a34a9d | COC(=O)C(C)CC(Cl)C(=O)O.O=S(Cl)Cl>>COC(=O)CCC(Cl)C(=O)Cl | ClC(C(=O)O)CC(C)C(=O)OC.S(=O)(Cl)Cl>>ClC(C(=O)Cl)CCC(=O)OC | C[CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][CH:7]([Cl:8])[C:9](O)=[O:10].O=S(Cl)[Cl:11]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH:7]([Cl:8])[C:9](=[O:10])[Cl:11] | COC(=O)C(C)CC(Cl)C(=O)O.O=S(Cl)Cl | COC(=O)CCC(Cl)C(=O)Cl | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 71853bac5dd0732e3d60bec8e19996dc831d229d490544ad9bbbb3710b2dc130 | f24a3ae28a4ec4bb4dccac7a59b48cf750266c146d0631e1527a9b06ebcd084a | null | C-[CH;D3;+0:1](-[C:2]-[C:3](-[Cl;D1;H0:4])-[C;H0;D3;+0:5](-O)=[O;D1;H0:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10].Cl-S(=O)-[Cl;H0;D1;+0:11]>>[C;D1;H3:10]-[#8:9]-[C:7](=[O;D1;H0:8])-[CH2;D2;+0:1]-[C:2]-[C:3](-[Cl;D1;H0:4])-[C;H0;D3;+0:5](-[Cl;H0;D1;+0:11])=[O;D1;H0:6] | null | [] | 80 | CELSIUS | 30 | MINUTE | A mixture of 7.6 g of 2-chloro-4-methoxycarbonyl valeric acid, 9.2 ml of thionyl chloride and 30 ml of toluene was stirred for 30 minutes at 80° C., followed by distilling off the solvent under reduced pressure to leave 2-chloro-4-methoxycarbonyl butyryl chloride. A mixture of this compound, 5.0 g of 2-benzylaminobenzo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester | Acyl halide.Ester | null | null | null | HCl | C1(=CC=CC=C1)C | 80 | 0.5 | COC(=O)C(C)CC(Cl)C(=O)O.O=S(Cl)Cl>C1(=CC=CC=C1)C>COC(=O)CCC(Cl)C(=O)Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a9d5932f47fc470faf0612928f6d7003 | COC(=O)C(C)CC(Cl)C(=O)O.O=S(Cl)Cl>>COC(=O)CCC(Cl)C(=O)Cl | ClC(C(=O)O)CC(C)C(=O)OC.S(=O)(Cl)Cl>>ClC(C(=O)Cl)CCC(=O)OC | C[CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][CH:7]([Cl:8])[C:9](O)=[O:10].O=S(Cl)[Cl:11]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH:7]([Cl:8])[C:9](=[O:10])[Cl:11] | COC(=O)C(C)CC(Cl)C(=O)O.O=S(Cl)Cl | COC(=O)CCC(Cl)C(=O)Cl | null | null | null | Functional Group Interconversion | OtherReaction | 71853bac5dd0732e3d60bec8e19996dc831d229d490544ad9bbbb3710b2dc130 | f24a3ae28a4ec4bb4dccac7a59b48cf750266c146d0631e1527a9b06ebcd084a | null | C-[CH;D3;+0:1](-[C:2]-[C:3](-[Cl;D1;H0:4])-[C;H0;D3;+0:5](-O)=[O;D1;H0:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10].Cl-S(=O)-[Cl;H0;D1;+0:11]>>[C;D1;H3:10]-[#8:9]-[C:7](=[O;D1;H0:8])-[CH2;D2;+0:1]-[C:2]-[C:3](-[Cl;D1;H0:4])-[C;H0;D3;+0:5](-[Cl;H0;D1;+0:11])=[O;D1;H0:6] | null | [] | null | null | null | null | A mixture of 6.2 g of 2-chloro-4-methoxycarbonyl valeric acid and 12.6 ml of thionyl chloride was refluxed for 30 minutes, then the solvent was distilled off under reduced pressure to leave 2-chloro-4-methoxycarbonyl butyryl chloride. A mixture of this product, 5.0 g of 2-benzylaminodiphenyl methanol, 100 ml of ethyl a... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester | Acyl halide.Ester | null | null | null | HCl | null | null | null | COC(=O)C(C)CC(Cl)C(=O)O.O=S(Cl)Cl>>COC(=O)CCC(Cl)C(=O)Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b5522d18fb004b81842dc376c274bba5 | COc1ccc(CN2C(=O)[C@@H](CC(=O)O)O[C@H](c3ccccc3Cl)c3cc(Cl)ccc32)c(OC)c1>>O=C(O)CC[C@H]1O[C@@H](c2ccccc2)c2ccccc2N(Cc2ccccc2)C1=O | Cl.ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC2=C(C=C(C=C2)OC)OC)=O)CC(=O)O)C2=C(C=CC=C2)Cl)C1.[OH-].[Na+]>>C(C1=CC=CC=C1)N1C([C@H](O[C@H](C2=C1C=CC=C2)C2=CC=CC=C2)CCC(=O)O)=O | CO[c:2]1[cH:25][c:24](O[CH3:26])[c:23]([CH2:22][N:21]2[c:20]3[c:15]([cH:16][c:17](Cl)[cH:18][cH:19]3)[C@@H:8]([c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3Cl)[O:7][C@H:6]([CH2:5][C:4](=[O:1])[OH:3])[C:29]2=[O:30])[cH:28][cH:27]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][C@H:6]1[O:7][C@@H:8]([c:9]2[cH:10][cH:11][cH:12][cH:13][cH:1... | COc1ccc(CN2C(=O)[C@@H](CC(=O)O)O[C@H](c3ccccc3Cl)c3cc(Cl)ccc32)c(OC)c1 | O=C(O)CC[C@H]1O[C@@H](c2ccccc2)c2ccccc2N(Cc2ccccc2)C1=O | null | null | CO | Miscellaneous | OtherReaction | 43bebc7a1611e70b5b5e71e81d8b4d741d8b8d1e70d6756d788764865343cbfc | 4ec579fe1c565a8ac8dd28a6e233bf9ed5ac66403ad6d60a497ae7f2aaa21688 | O=C1CO[C@@H](c2ccccc2)c2ccccc2N1Cc1ccccc1 | C-O-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c;H0;D3;+0:3](-O-[CH3;D1;+0:4]):[c:5](-[C:6]-[#7:7]-[C:8](=[O;D1;H0:9])-[C:10](-[C:11]-[C;H0;D3;+0:12](=[O;H0;D1;+0:13])-[OH;D1;+0:14])-[#8:15]-[C:16](-[c:17](:[c:18]):[c;H0;D3;+0:19](-Cl):[c:20]:[c:21])-[c:22]:[c:23]:[c;H0;D3;+0:24](-Cl):[c:25]:[c:26]):[c:27]:[cH;D2;+0:28]:1>>[O;D1;H0... | null | [] | null | null | 30 | MINUTE | In 20 ml of methanol was dissolved 0.5 g of ethyl ester of cis-1-benzyl-2-oxo-5-phenyl-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-propionic acid obtained in Example 8. To the solution was added 7 ml of 1N sodium hydroxide, and the mixture was stirred for 30 minutes at room temperature. The reaction mixture was acidified wi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Carboxylic acid.Ether.Ether | Carboxylic acid | c1ccccc1.c1ccccc1.c1ccc2c(c1)COCC[NH]2 | c1ccccc1.c1ccc2c(c1)COCC[NH]2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)COCC[NH]2.c1ccccc1 | Other | CO | null | 0.5 | COc1ccc(CN2C(=O)[C@@H](CC(=O)O)O[C@H](c3ccccc3Cl)c3cc(Cl)ccc32)c(OC)c1>CO>O=C(O)CC[C@H]1O[C@@H](c2ccccc2)c2ccccc2N(Cc2ccccc2)C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-14c74de0439b4c7ab9a7a1cfbae36b8f | O=C(O)CC[C@H]1O[C@H](c2ccccc2)c2ccccc2N(Cc2ccccc2)C1=O>>O=C1[C@@H](CCCO)O[C@H](c2ccccc2)c2ccccc2N1Cc1ccccc1 | C(C1=CC=CC=C1)N1C([C@H](O[C@@H](C2=C1C=CC=C2)C2=CC=CC=C2)CCC(=O)O)=O.[BH4-].[Na+].[Cl-].[Li+].Cl>>C(C1=CC=CC=C1)N1C([C@H](O[C@@H](C2=C1C=CC=C2)C2=CC=CC=C2)CCCO)=O | O=[C:6]([CH2:5][CH2:4][C@@H:3]1[C:2](=[O:1])[N:22]([CH2:23][c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[c:21]2[c:16]([cH:17][cH:18][cH:19][cH:20]2)[C@@H:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[O:8]1)[OH:7]>>[O:1]=[C:2]1[C@@H:3]([CH2:4][CH2:5][CH2:6][OH:7])[O:8][C@H:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2... | O=C(O)CC[C@H]1O[C@H](c2ccccc2)c2ccccc2N(Cc2ccccc2)C1=O | O=C1[C@@H](CCCO)O[C@H](c2ccccc2)c2ccccc2N1Cc1ccccc1 | null | null | C(C)O.C(C)(=O)OCC.O1CCCC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | O=C1CO[C@H](c2ccccc2)c2ccccc2N1Cc1ccccc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:1]-[O;D1;H1:2] | null | [] | null | null | 10 | MINUTE | The mixture of 0.4 g of methyl ester of trans-1-benzyl2-oxo-5-phenyl-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-propionic acid obtained in Example 12, 0.16 g of sodium borohydride and 0.16 g of lithium chloride in 15 ml of tetrahydrofuran were stirred for 10 minutes at room temperature. To the resultant was added 30 ml of ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1.c1ccc2c(c1)COCC[NH]2.c1ccccc1 | Other | C(C)O.C(C)(=O)OCC.O1CCCC1 | null | 0.166667 | O=C(O)CC[C@H]1O[C@H](c2ccccc2)c2ccccc2N(Cc2ccccc2)C1=O>C(C)O.C(C)(=O)OCC.O1CCCC1>O=C1[C@@H](CCCO)O[C@H](c2ccccc2)c2ccccc2N1Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b53797564a374067960a6e48c29544d3 | O=C(O)C[C@H]1O[C@H](c2ccccc2Cl)c2cc(Cl)ccc2N(Cc2ccccc2)C1=O.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>>Cl.NC[C@H]1O[C@H](c2ccccc2Cl)c2cc(Cl)ccc2N(Cc2ccccc2)C1=O | C(C1=CC=CC=C1)N1C([C@H](O[C@@H](C2=C1C=CC(=C2)Cl)C2=C(C=CC=C2)Cl)CC(=O)O)=O.C(C)N(CC)CC.C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-]>>Cl.C(C1=CC=CC=C1)N1C([C@H](O[C@@H](C2=C1C=CC(=C2)Cl)C2=C(C=CC=C2)Cl)CN)=O | O=C(O)[CH2:3][C@H:4]1[O:5][C@H:6]([c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[Cl:1])[c:14]2[cH:15][c:16]([Cl:17])[cH:18][cH:19][c:20]2[N:21]([CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[C:29]1=[O:30].[N-]=[N+]=[N:2]P(=O)(c1ccccc1)c1ccccc1>>[ClH:1].[NH2:2][CH2:3][C@H:4]1[O:5][C@H:6]([c:7]2[cH:8][cH:9][cH:10][cH:11][... | O=C(O)C[C@H]1O[C@H](c2ccccc2Cl)c2cc(Cl)ccc2N(Cc2ccccc2)C1=O.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1 | Cl.NC[C@H]1O[C@H](c2ccccc2Cl)c2cc(Cl)ccc2N(Cc2ccccc2)C1=O | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 1f1b04abeaffa1cd0dbeadbc846df91a86d79cd0794def0b7d63e085a5b52d11 | ace9751e95272b0dafda873c7583ab20489d68697a41c7be5b84ad07fe14a502 | O=C1CO[C@H](c2ccccc2)c2ccccc2N1Cc1ccccc1 | O-C(=O)-[CH2;D2;+0:1]-[C:2](-[#8:3]-[C:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[Cl;H0;D1;+0:8]):[c:9]:[c:10])-[C:11](=[O;D1;H0:12])-[#7:13](-[C:14])-[c:15].O=P(-[N;H0;D2;+0:16]=[N+]=[N-])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:14]-[#7:13](-[c:15])-[C:11](=[O;D1;H0:12])-[C:2](-[CH2;D2;+0:1]-[NH2;D1;+0:16])-[#8:3]-[C:4]-[c:5](:[c:... | null | [] | null | null | null | null | In 5 ml of dimethylformamide was dissolved 1.0 g of trans-1-benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid obtained obtained in Reference Example 5. To the solution was added 0.3 ml of triethylamine, to which was added dropwise, while stirring under ice-cooling, 0.6 g of dip... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid.Azide | Aromatic halide.Primary amine | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2c(c1)COCC[NH]2.c1ccccc1 | HO- | CN(C=O)C | null | null | O=C(O)C[C@H]1O[C@H](c2ccccc2Cl)c2cc(Cl)ccc2N(Cc2ccccc2)C1=O.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>CN(C=O)C>Cl.NC[C@H]1O[C@H](c2ccccc2Cl)c2cc(Cl)ccc2N(Cc2ccccc2)C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e1cdebf350904ceba1f779d1bab6a752 | C=O.O=C(O)CNC[C@H]1O[C@H](c2ccccc2Cl)c2cc(Cl)ccc2N(Cc2ccccc2)C1=O>>CN(CC(=O)O)C[C@H]1O[C@H](c2ccccc2Cl)c2cc(Cl)ccc2N(Cc2ccccc2)C1=O | C(C1=CC=CC=C1)N1C([C@H](O[C@@H](C2=C1C=CC(=C2)Cl)C2=C(C=CC=C2)Cl)CNCC(=O)O)=O.C=O.C(C(=O)O)(=O)O>>C(C1=CC=CC=C1)N1C([C@H](O[C@@H](C2=C1C=CC(=C2)Cl)C2=C(C=CC=C2)Cl)CN(CC(=O)O)C)=O | O=[CH2:1].[NH:2]([CH2:3][C:4](=[O:5])[OH:6])[CH2:7][C@H:8]1[O:9][C@H:10]([c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[Cl:17])[c:18]2[cH:19][c:20]([Cl:21])[cH:22][cH:23][c:24]2[N:25]([CH2:26][c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[C:33]1=[O:34]>>[CH3:1][N:2]([CH2:3][C:4](=[O:5])[OH:6])[CH2:7][C@H:8]1[O:9][C@H:10]([c:... | C=O.O=C(O)CNC[C@H]1O[C@H](c2ccccc2Cl)c2cc(Cl)ccc2N(Cc2ccccc2)C1=O | CN(CC(=O)O)C[C@H]1O[C@H](c2ccccc2Cl)c2cc(Cl)ccc2N(Cc2ccccc2)C1=O | null | null | null | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Secondary Amine Methylation | deb0f39510ff32c3bd75ceaf7ece4070b1f686ff120d798ccd640765025dab3c | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | O=C1CO[C@H](c2ccccc2)c2ccccc2N1Cc1ccccc1 | O=[CH2;D1;+0:1].[#7:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9](=[O;D1;H0:10])-[O;D1;H1:11])-[#8:12]>>[#7:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6]-[N;H0;D3;+0:7](-[CH3;D1;+0:1])-[C:8]-[C:9](=[O;D1;H0:10])-[O;D1;H1:11])-[#8:12] | null | [] | 80 | CELSIUS | 2 | HOUR | To 0.13 g of ethyl ester of N-[trans-1-benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-ylmethyl]glycine obtained in Example 40 were added 2 ml of formalin and 2 ml of oxalic acid: The mixture was heated at 80° C. for 2 hours. The reaction mixture was concentrated under reduced pressure, a... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccc2c(c1)COCC[NH]2.c1ccccc1 | Other | null | 80 | 2 | C=O.O=C(O)CNC[C@H]1O[C@H](c2ccccc2Cl)c2cc(Cl)ccc2N(Cc2ccccc2)C1=O>>CN(CC(=O)O)C[C@H]1O[C@H](c2ccccc2Cl)c2cc(Cl)ccc2N(Cc2ccccc2)C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-55b206274ba64afda97796f6ecfc93a5 | CC(=O)OC(C)=O.O=C(O)CNC[C@H]1O[C@H](c2ccccc2Cl)c2cc(Cl)ccc2N(Cc2ccccc2)C1=O>>CC(=O)N(CC(=O)O)C[C@H]1O[C@H](c2ccccc2Cl)c2cc(Cl)ccc2N(Cc2ccccc2)C1=O | C(C1=CC=CC=C1)N1C([C@H](O[C@@H](C2=C1C=CC(=C2)Cl)C2=C(C=CC=C2)Cl)CNCC(=O)O)=O.C(C)(=O)OC(C)=O.C(C)N(CC)CC>>C(C1=CC=CC=C1)N1C([C@H](O[C@@H](C2=C1C=CC(=C2)Cl)C2=C(C=CC=C2)Cl)CN(CC(=O)O)C(C)=O)=O | CC(=O)O[C:2]([CH3:1])=[O:3].[NH:4]([CH2:5][C:6](=[O:7])[OH:8])[CH2:9][C@H:10]1[O:11][C@H:12]([c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[Cl:19])[c:20]2[cH:21][c:22]([Cl:23])[cH:24][cH:25][c:26]2[N:27]([CH2:28][c:29]2[cH:30][cH:31][cH:32][cH:33][cH:34]2)[C:35]1=[O:36]>>[CH3:1][C:2](=[O:3])[N:4]([CH2:5][C:6](=[O:7])[OH:8]... | CC(=O)OC(C)=O.O=C(O)CNC[C@H]1O[C@H](c2ccccc2Cl)c2cc(Cl)ccc2N(Cc2ccccc2)C1=O | CC(=O)N(CC(=O)O)C[C@H]1O[C@H](c2ccccc2Cl)c2cc(Cl)ccc2N(Cc2ccccc2)C1=O | null | null | CO | Acylation | Aminolysis of esters | 72a6d1966b6b15ac7195d4682af251dc9ffac857f784a4242970ab5c7a529369 | 6593c6062585994f02076cd3c86920ae7244b86659eab65c21b5a8628c6d4bb8 | O=C1CO[C@H](c2ccccc2)c2ccccc2N1Cc1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7:4]-[C:5](=[O;D1;H0:6])-[C:7](-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11](=[O;D1;H0:12])-[O;D1;H1:13])-[#8:14]>>[#7:4]-[C:5](=[O;D1;H0:6])-[C:7](-[C:8]-[N;H0;D3;+0:9](-[C:10]-[C:11](=[O;D1;H0:12])-[O;D1;H1:13])-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[#8:14] | null | [] | null | null | null | null | In 4 ml of methanol was dissolved 60 mg of ethyl ester of N-[trans-1-benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-ylmethyl]glycine obtained in Example 40. To the solution were added 0.2 ml of acetic anhydride and 0.2 ml of triethylamine. The mixture was heated for one hour under reflux... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccc2c(c1)COCC[NH]2.c1ccccc1 | HO- | CO | null | null | CC(=O)OC(C)=O.O=C(O)CNC[C@H]1O[C@H](c2ccccc2Cl)c2cc(Cl)ccc2N(Cc2ccccc2)C1=O>CO>CC(=O)N(CC(=O)O)C[C@H]1O[C@H](c2ccccc2Cl)c2cc(Cl)ccc2N(Cc2ccccc2)C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-42aca8051c1945bf90df0b26f4fe3c47 | O=C1[C@@H](CO)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc2N1Cc1ccccc1>>O=C(O)[C@H]1O[C@H](c2ccccc2Cl)c2cc(Cl)ccc2N(Cc2ccccc2)C1=O | C(C1=CC=CC=C1)N1C([C@H](O[C@@H](C2=C1C=CC(=C2)Cl)C2=C(C=CC=C2)Cl)CO)=O.CC(=O)C.OS(=O)(=O)O.O=[Cr](=O)=O>>C(C1=CC=CC=C1)N1C([C@H](O[C@@H](C2=C1C=CC(=C2)Cl)C2=C(C=CC=C2)Cl)C(=O)O)=O | [CH2:2]([OH:3])[C@H:4]1[O:5][C@H:6]([c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[Cl:13])[c:14]2[cH:15][c:16]([Cl:17])[cH:18][cH:19][c:20]2[N:21]([CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[C:29]1=[O:30]>>[O:1]=[C:2]([OH:3])[C@H:4]1[O:5][C@H:6]([c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[Cl:13])[c:14]2[cH:15][c:16]([Cl:... | O=C1[C@@H](CO)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc2N1Cc1ccccc1 | O=C(O)[C@H]1O[C@H](c2ccccc2Cl)c2cc(Cl)ccc2N(Cc2ccccc2)C1=O | null | null | CC(=O)C | Oxidation | Oxidation of alcohol to carboxylic acid | b709baac44a995a9a8f6386a6b5d87f98c32eb5a0636340abc1f778fae827230 | 4454822e22dc2dc24e7495385256bfce456e337c240bb764261f81dbeda1aaa1 | O=C1CO[C@H](c2ccccc2)c2ccccc2N1Cc1ccccc1 | [C:1]-[#7:2](-[c:3])-[C:4](=[O;D1;H0:5])-[C:6](-[CH2;D2;+0:7]-[O;D1;H1:8])-[#8:9]-[C:10]>>[C:1]-[#7:2](-[c:3])-[C:4](=[O;D1;H0:5])-[C:6](-[C;H0;D3;+0:7](=[O;D1;H0:11])-[O;D1;H1:8])-[#8:9]-[C:10] | null | [] | null | null | null | null | In 20 ml of acetone was dissolved 0.5 g of trans-1-benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-methanol obtained in Example 46. To the solution was added dropwise, while stirring at room temperature, 0.5 ml of a Jones reagent. The reaction mixture was stirred for one hour at room tem... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Carboxylic acid | null | null | c1ccccc1.c1ccc2c(c1)COCC[NH]2.c1ccccc1 | Other | CC(=O)C | null | null | O=C1[C@@H](CO)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc2N1Cc1ccccc1>CC(=O)C>O=C(O)[C@H]1O[C@H](c2ccccc2Cl)c2cc(Cl)ccc2N(Cc2ccccc2)C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a28f563304e54fffb04c32e3c16b18c3 | CCOC(=O)CNC(=O)C[C@H]1O[C@@H](c2ccccc2)c2cc(Cl)ccc2N(C(C)C)C1=O>>CC(C)N1C(=O)[C@@H](CC(=O)NCC(=O)O)O[C@@H](c2ccccc2)c2cc(Cl)ccc21 | C(C)OC(CNC(C[C@@H]1C(N(C2=C([C@@H](O1)C1=CC=CC=C1)C=C(C=C2)Cl)C(C)C)=O)=O)=O.C([O-])([O-])=O.[K+].[K+].Cl>>ClC=1C=CC2=C([C@@H](O[C@@H](C(N2C(C)C)=O)CC(=O)NCC(=O)O)C2=CC=CC=C2)C1 | CC[O:15][C:13]([CH2:12][NH:11][C:9]([CH2:8][C@@H:7]1[C:5](=[O:6])[N:4]([CH:2]([CH3:1])[CH3:3])[c:30]2[c:24]([cH:25][c:26]([Cl:27])[cH:28][cH:29]2)[C@H:17]([c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[O:16]1)=[O:10])=[O:14]>>[CH3:1][CH:2]([CH3:3])[N:4]1[C:5](=[O:6])[C@@H:7]([CH2:8][C:9](=[O:10])[NH:11][CH2:12][C:13](=[O... | CCOC(=O)CNC(=O)C[C@H]1O[C@@H](c2ccccc2)c2cc(Cl)ccc2N(C(C)C)C1=O | CC(C)N1C(=O)[C@@H](CC(=O)NCC(=O)O)O[C@@H](c2ccccc2)c2cc(Cl)ccc21 | null | null | CO.O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1CO[C@@H](c2ccccc2)c2ccccc2N1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 64.4 | [{"value": 64.4, "product": "ClC=1C=CC2=C([C@@H](O[C@@H](C(N2C(C)C)=O)CC(=O)NCC(=O)O)C2=CC=CC=C2)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | In a mixture of 2 ml of methanol and 1 ml of water was suspended 48 mg of N-(trans-7-chloro-1-isopropyl-5-phenyl-1,2,3,5-tetrahydro-2-oxo-4,1-benzoxazepin-3-ylacetyl)glycine ethyl ester obtained in Example 55. To the suspension was added 0.1 g of potassium carbonate. The mixture was stirred for 6 hours at room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2c(c1)COCC[NH]2 | Other | CO.O | null | 6 | CCOC(=O)CNC(=O)C[C@H]1O[C@@H](c2ccccc2)c2cc(Cl)ccc2N(C(C)C)C1=O>CO.O>CC(C)N1C(=O)[C@@H](CC(=O)NCC(=O)O)O[C@@H](c2ccccc2)c2cc(Cl)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-848ec5bd613e4f5c9be2f2b670bc528c | CC(C)N1C(=O)[C@@H](CCO)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21>>CC(C)N1C(=O)[C@@H](CC=O)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 | CS(=O)C.C(C(=O)Cl)(=O)Cl.ClC=1C=CC2=C([C@H](O[C@@H](C(N2C(C)C)=O)CCO)C2=C(C=CC=C2)Cl)C1.C(C)N(CC)CC>>ClC=1C=CC2=C([C@H](O[C@@H](C(N2C(C)C)=O)CC=O)C2=C(C=CC=C2)Cl)C1 | [CH3:1][CH:2]([CH3:3])[N:4]1[C:5](=[O:6])[C@@H:7]([CH2:8][CH2:9][OH:10])[O:11][C@H:12]([c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[Cl:19])[c:20]2[cH:21][c:22]([Cl:23])[cH:24][cH:25][c:26]21>>[CH3:1][CH:2]([CH3:3])[N:4]1[C:5](=[O:6])[C@@H:7]([CH2:8][CH:9]=[O:10])[O:11][C@H:12]([c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[C... | CC(C)N1C(=O)[C@@H](CCO)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 | CC(C)N1C(=O)[C@@H](CC=O)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | O=C1CO[C@H](c2ccccc2)c2ccccc2N1 | [#7:1]-[C:2](=[O;D1;H0:3])-[C:4](-[C:5]-[CH2;D2;+0:6]-[OH;D1;+0:7])-[#8:8]>>[#7:1]-[C:2](=[O;D1;H0:3])-[C:4](-[C:5]-[CH;D2;+0:6]=[O;H0;D1;+0:7])-[#8:8] | 92.5 | [{"value": 92.5, "product": "ClC=1C=CC2=C([C@H](O[C@@H](C(N2C(C)C)=O)CC=O)C2=C(C=CC=C2)Cl)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | A solution of oxalyl chloride (0.72 ml) in methylene chloride (10 ml) was cooled to -65° C., to which was added dropwise a solution of dimethyl sulfoxide (0.63 ml) in methylene chloride (2 ml) taking 5 minutes, followed by stirring for 5 minutes. To the mixture was added dropwise, taking 15 minutes, a solution of trans... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1.c1ccc2c(c1)COCC[NH]2 | null | C(Cl)Cl | null | 0.083333 | CC(C)N1C(=O)[C@@H](CCO)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21>C(Cl)Cl>CC(C)N1C(=O)[C@@H](CC=O)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7891886a1dce4bd98201a13284a39c9a | CC(C)N1C(=O)[C@@H](CC=O)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21.CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1>>CC(C)N1C(=O)[C@@H](C/C=C/C(=O)O)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 | ClC=1C=CC2=C([C@H](O[C@@H](C(N2C(C)C)=O)CC=O)C2=C(C=CC=C2)Cl)C1.C(C)OC(=O)C=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>ClC=1C=CC2=C([C@H](O[C@@H](C(N2C(C)C)=O)C/C=C/C(=O)O)C2=C(C=CC=C2)Cl)C1 | O=[CH:9][CH2:8][C@@H:7]1[C:5](=[O:6])[N:4]([CH:2]([CH3:1])[CH3:3])[c:29]2[c:23]([cH:24][c:25]([Cl:26])[cH:27][cH:28]2)[C@@H:15]([c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[Cl:22])[O:14]1.CC[O:13][C:11]([CH:10]=P(c1ccccc1)(c1ccccc1)c1ccccc1)=[O:12]>>[CH3:1][CH:2]([CH3:3])[N:4]1[C:5](=[O:6])[C@@H:7]([CH2:8]/[CH:9]=[CH:10]... | CC(C)N1C(=O)[C@@H](CC=O)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21.CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1 | CC(C)N1C(=O)[C@@H](C/C=C/C(=O)O)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | c06f441329a1c85dd58b67c3ed7dca4f2b4838e56125ed608c5d39ebec591cc0 | 04a7a14866317f7132eb69ea35ca8b6703c51b03c0c51c392001b195de1edfe7 | O=C1CO[C@H](c2ccccc2)c2ccccc2N1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[CH;D2;+0:4]=P(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.O=[CH;D2;+0:5]-[C:6]-[C:7](-[#8:8])-[C:9](=[O;D1;H0:10])-[#7:11]>>[#7:11]-[C:9](=[O;D1;H0:10])-[C:7](-[C:6]/[CH;D2;+0:5]=[CH;D2;+0:4]/[C:2](=[O;D1;H0:3])-[OH;D1;+0:1])-[#8:8] | 77.1 | [{"value": 77.1, "product": "ClC=1C=CC2=C([C@H](O[C@@H](C(N2C(C)C)=O)C/C=C/C(=O)O)C2=C(C=CC=C2)Cl)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 3 | HOUR | In toluene (20 ml) was dissolved trans-7-chloro-5-(2-chlorophenyl)-1-isopropyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetaldehyde (1.5 g). To the solution was added (ethoxycarbonylmethylene)-triphenylphosphorane (2.0 g), and the mixture was stirred for 3 hours at 90° C. The solvent was distilled off, and the res... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Carboxylic acid | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)COCC[NH]2 | HO- | C1(=CC=CC=C1)C | 90 | 3 | CC(C)N1C(=O)[C@@H](CC=O)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21.CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1>C1(=CC=CC=C1)C>CC(C)N1C(=O)[C@@H](C/C=C/C(=O)O)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a2fcb8e364ca4dd2ada72db56fde3611 | CC(C)N1C(=O)[C@@H](C/C=C/C(=O)O)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21>>CC(C)N1C(=O)[C@@H](CCCC(=O)O)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 | ClC=1C=CC2=C([C@H](O[C@@H](C(N2C(C)C)=O)C/C=C/C(=O)O)C2=C(C=CC=C2)Cl)C1.[H][H]>>ClC=1C=CC2=C([C@H](O[C@@H](C(N2C(C)C)=O)CCCC(=O)O)C2=C(C=CC=C2)Cl)C1 | [CH3:1][CH:2]([CH3:3])[N:4]1[C:5](=[O:6])[C@@H:7]([CH2:8]/[CH:9]=[CH:10]/[C:11](=[O:12])[OH:13])[O:14][C@H:15]([c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[Cl:22])[c:23]2[cH:24][c:25]([Cl:26])[cH:27][cH:28][c:29]21>>[CH3:1][CH:2]([CH3:3])[N:4]1[C:5](=[O:6])[C@@H:7]([CH2:8][CH2:9][CH2:10][C:11](=[O:12])[OH:13])[O:14][C@H:... | CC(C)N1C(=O)[C@@H](C/C=C/C(=O)O)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 | CC(C)N1C(=O)[C@@H](CCCC(=O)O)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 | null | [C].[Pd] | C(C)(=O)OCC | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | O=C1CO[C@H](c2ccccc2)c2ccccc2N1 | [#7:1]-[C:2](=[O;D1;H0:3])-[C:4](-[C:5]/[CH;D2;+0:6]=[CH;D2;+0:7]/[C:8](=[O;D1;H0:9])-[O;D1;H1:10])-[#8:11]>>[#7:1]-[C:2](=[O;D1;H0:3])-[C:4](-[C:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10])-[#8:11] | 81.8 | [{"value": 81.8, "product": "ClC=1C=CC2=C([C@H](O[C@@H](C(N2C(C)C)=O)CCCC(=O)O)C2=C(C=CC=C2)Cl)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In ethyl acetate (20 ml) was dissolved ethyl ester of trans-7-chloro-5-(2-chlorophenyl)-1-isopropyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-crotonic acid (0.45 g). To the solution was added 10% palladium carbon (0.1 g), and the mixture was subjected to catalytic reduction at room temperatures under atmospheric pre... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccc2c(c1)COCC[NH]2 | null | [C].[Pd].C(C)(=O)OCC | null | null | CC(C)N1C(=O)[C@@H](C/C=C/C(=O)O)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21>[C].[Pd].C(C)(=O)OCC>CC(C)N1C(=O)[C@@H](CCCC(=O)O)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-058d1ba117d240a89d29098d17908733 | COc1cc(OC)c(C(=O)c2cc(Cl)ccc2NC(C)=O)c(OC)c1>>COc1cc(OC)c(C(=O)c2cc(Cl)ccc2N)c(OC)c1 | C(C)(=O)NC1=C(C(=O)C2=C(C=C(C=C2OC)OC)OC)C=C(C=C1)Cl.Cl>>NC1=C(C(=O)C2=C(C=C(C=C2OC)OC)OC)C=C(C=C1)Cl | CC(=O)[NH:18][c:17]1[c:11]([C:9]([c:8]2[c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[cH:22][c:19]2[O:20][CH3:21])=[O:10])[cH:12][c:13]([Cl:14])[cH:15][cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8]([C:9](=[O:10])[c:11]2[cH:12][c:13]([Cl:14])[cH:15][cH:16][c:17]2[NH2:18])[c:19]([O:20][CH3:21])[cH:22]1 | COc1cc(OC)c(C(=O)c2cc(Cl)ccc2NC(C)=O)c(OC)c1 | COc1cc(OC)c(C(=O)c2cc(Cl)ccc2N)c(OC)c1 | null | null | C(C)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | O=C(c1ccccc1)c1ccccc1 | C-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5]=[O;D1;H0:6]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]-[C:5]=[O;D1;H0:6] | 90.2 | [{"value": 90.2, "product": "NC1=C(C(=O)C2=C(C=C(C=C2OC)OC)OC)C=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4.7 g of 2-acetylamino-5-chloro-2',4',6'-trimethoxybenzophenone, 50 ml of 6N hydrochloric acid and 50 ml of ethanol was refluxed for 1 hour while heating. After the solvent was distilled off, the residue was basefied with an aqueous solution of sodium hydrogen carbonate and then extracted with ethyl acetat... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccccc1.c1ccccc1 | HO- | C(C)O | null | null | COc1cc(OC)c(C(=O)c2cc(Cl)ccc2NC(C)=O)c(OC)c1>C(C)O>COc1cc(OC)c(C(=O)c2cc(Cl)ccc2N)c(OC)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4ec01e77712840338ca5e710ce372103 | COc1cc(OC)c(C(=O)c2cc(Cl)ccc2N)c(OC)c1>>COc1cc(OC)c(C(O)c2cc(Cl)ccc2N)c(OC)c1 | O.NC1=C(C(=O)C2=C(C=C(C=C2OC)OC)OC)C=C(C=C1)Cl.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>NC1=C(C(C2=C(C=C(C=C2OC)OC)OC)O)C=C(C=C1)Cl | [CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8]([C:9](=[O:10])[c:11]2[cH:12][c:13]([Cl:14])[cH:15][cH:16][c:17]2[NH2:18])[c:19]([O:20][CH3:21])[cH:22]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8]([CH:9]([OH:10])[c:11]2[cH:12][c:13]([Cl:14])[cH:15][cH:16][c:17]2[NH2:18])[c:19]([O:20][CH3:21])[cH:22]1 | COc1cc(OC)c(C(=O)c2cc(Cl)ccc2N)c(OC)c1 | COc1cc(OC)c(C(O)c2cc(Cl)ccc2N)c(OC)c1 | null | null | O1CCCC1 | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(Cc2ccccc2)cc1 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8]>>[OH;D1;+0:1]-[CH;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8] | 96.1 | [{"value": 96.1, "product": "NC1=C(C(C2=C(C=C(C=C2OC)OC)OC)O)C=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 3.0 g of 2-amino-5-chloro-2',4',6'-trimethoxybenzophenone in 50 ml of tetrahydrofuran, 0.43 g of lithium aluminum hydride was added, followed by stirring for 1 hour. After water was added, the solution was extracted with ethyl acetate and dried over anhydrous sodium sulfate, after which the solvent was... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccccc1.c1ccccc1 | null | O1CCCC1 | null | 1 | COc1cc(OC)c(C(=O)c2cc(Cl)ccc2N)c(OC)c1>O1CCCC1>COc1cc(OC)c(C(O)c2cc(Cl)ccc2N)c(OC)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-775bed0ad28c49fbb6c1ce5df50c6d65 | CC(C)(C)C=O.COc1cc(OC)c(C(O)c2cc(Cl)ccc2N)c(OC)c1>>COc1cc(OC)c(C(O)c2cc(Cl)ccc2NCC(C)(C)C)c(OC)c1 | C(#N)[BH3-].[Na+].NC1=C(C(C2=C(C=C(C=C2OC)OC)OC)O)C=C(C=C1)Cl.CC(C=O)(C)C.C(C)(=O)O>>ClC=1C=CC(=C(C(C2=C(C=C(C=C2OC)OC)OC)O)C1)NCC(C)(C)C | O=[CH:19][C:20]([CH3:21])([CH3:22])[CH3:23].[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8]([CH:9]([OH:10])[c:11]2[cH:12][c:13]([Cl:14])[cH:15][cH:16][c:17]2[NH2:18])[c:24]([O:25][CH3:26])[cH:27]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8]([CH:9]([OH:10])[c:11]2[cH:12][c:13]([Cl:14])[cH:15][cH:16][c:17]2[NH:18]... | CC(C)(C)C=O.COc1cc(OC)c(C(O)c2cc(Cl)ccc2N)c(OC)c1 | COc1cc(OC)c(C(O)c2cc(Cl)ccc2NCC(C)(C)C)c(OC)c1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(Cc2ccccc2)cc1 | O=[CH;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C;D1;H3:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:3]-[C:2](-[C;D1;H3:4])(-[C;D1;H3:5])-[CH2;D2;+0:1]-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | 8 | HOUR | After a solution of 2.5 g of 2-amino-5-chloro-α-(2,4,6-trimethoxyphenyl)benzyl alcohol, 1.01 ml of trimethylacetaldehyde and 0.56 g of acetic acid in 30 ml of ethanol was stirred at room temperature for 1.5 hours, 0.81 g of sodium cyanoborohydride was added, followed by stirring overnight. After concentration and subse... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | Other | C(C)O | null | 8 | CC(C)(C)C=O.COc1cc(OC)c(C(O)c2cc(Cl)ccc2N)c(OC)c1>C(C)O>COc1cc(OC)c(C(O)c2cc(Cl)ccc2NCC(C)(C)C)c(OC)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1fc2f1e399f34cafb24dd477e3e8aa29 | CC(C)CN1C(=O)[C@@H](CC(=O)O)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21.[NH4+]>>CC(C)CN1C(=O)[C@@H](CC(N)=O)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 | ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)C)=O)CC(=O)O)C2=C(C=CC=C2)Cl)C1.[Cl-].[NH4+].Cl.C(C)N=C=NCCCN(C)C.C(C)N(CC)CC>>ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)C)=O)CC(=O)N)C2=C(C=CC=C2)Cl)C1 | O[C:10]([CH2:9][C@@H:8]1[C:6](=[O:7])[N:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:28]2[c:22]([cH:23][c:24]([Cl:25])[cH:26][cH:27]2)[C@@H:14]([c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[Cl:21])[O:13]1)=[O:12].[NH4+:11]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[C@@H:8]([CH2:9][C:10]([NH2:11])=[O:12])[O:13][C@H:14]([c:15... | CC(C)CN1C(=O)[C@@H](CC(=O)O)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21.[NH4+] | CC(C)CN1C(=O)[C@@H](CC(N)=O)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 | null | null | CN(C=O)C.O | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | O=C1CO[C@H](c2ccccc2)c2ccccc2N1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4](-[#8:5])-[C:6](=[O;D1;H0:7])-[#7:8].[NH4+;D0:9]>>[#7:8]-[C:6](=[O;D1;H0:7])-[C:4](-[C:3]-[C;H0;D3;+0:1](-[NH2;D1;+0:9])=[O;D1;H0:2])-[#8:5] | 75.2 | [{"value": 75.2, "product": "ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)C)=O)CC(=O)N)C2=C(C=CC=C2)Cl)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 1.0 g of trans-7-chloro-5-(2-chlorophenyl)-1-isobutyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid and 0.5 g of ammonium chloride were dissolved in 8 mi of dimethylformamide, and 0.46 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 0.7 ml of triethylamine were added, followed by stirrin... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccccc1.c1ccc2c(c1)COCC[NH]2 | HO- | CN(C=O)C.O | null | 0.5 | CC(C)CN1C(=O)[C@@H](CC(=O)O)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21.[NH4+]>CN(C=O)C.O>CC(C)CN1C(=O)[C@@H](CC(N)=O)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-39af1e12beb24e17a8267182051aa7af | Nc1ccc(Cl)cc1C(O)c1ccccc1Cl.O=C(O)C(F)(F)F>>O=C(Nc1ccc(Cl)cc1C(O)c1ccccc1Cl)C(F)(F)F | NC1=C(C(C2=C(C=CC=C2)Cl)O)C=C(C=C1)Cl.FC(C(=O)O)(F)F.C(O)([O-])=O.[Na+]>>ClC=1C=CC(=C(C(C2=C(C=CC=C2)Cl)O)C1)NC(C(F)(F)F)=O | [NH2:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][c:10]1[CH:11]([OH:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[Cl:19].O[C:2](=[O:1])[C:20]([F:21])([F:22])[F:23]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][c:10]1[CH:11]([OH:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[Cl:19])[C:20]([F:21])([F:22])[F:23] | Nc1ccc(Cl)cc1C(O)c1ccccc1Cl.O=C(O)C(F)(F)F | O=C(Nc1ccc(Cl)cc1C(O)c1ccccc1Cl)C(F)(F)F | null | null | ClCCl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(Cc2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[F;D1;H0:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[F;D1;H0:4]-[C:3](-[F;D1;H0:5])(-[F;D1;H0:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 95.7 | [{"value": 95.7, "product": "ClC=1C=CC(=C(C(C2=C(C=CC=C2)Cl)O)C1)NC(C(F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.0 g of 2-amino-5-chloro-α-(2-chlorophenyl)benzyl alcohol in 12 ml of dichloromethane, a solution of 0.8 g of anhydrous trifluoroacetic acid in 2 ml of dichloromethane was added. After reaction, an aqueous solution of sodium hydrogen carbonate was added, and the organic layer was dried, after which th... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | ClCCl | null | null | Nc1ccc(Cl)cc1C(O)c1ccccc1Cl.O=C(O)C(F)(F)F>ClCCl>O=C(Nc1ccc(Cl)cc1C(O)c1ccccc1Cl)C(F)(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-043e8eba8ec84c2aabee85de8361dc19 | O=C(Nc1ccc(Cl)cc1C(O)c1ccccc1Cl)C(F)(F)F>>OC(c1ccccc1Cl)c1cc(Cl)ccc1NCC(F)(F)F | [H-].[Al+3].[Li+].[H-].[H-].[H-].ClC=1C=CC(=C(C(C2=C(C=CC=C2)Cl)O)C1)NC(C(F)(F)F)=O.O>>ClC=1C=CC(=C(C(C2=C(C=CC=C2)Cl)O)C1)NCC(F)(F)F | O=[C:18]([NH:17][c:16]1[c:10]([CH:2]([OH:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[Cl:9])[cH:11][c:12]([Cl:13])[cH:14][cH:15]1)[C:19]([F:20])([F:21])[F:22]>>[OH:1][CH:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[Cl:9])[c:10]1[cH:11][c:12]([Cl:13])[cH:14][cH:15][c:16]1[NH:17][CH2:18][C:19]([F:20])([F:21])[F:22] | O=C(Nc1ccc(Cl)cc1C(O)c1ccccc1Cl)C(F)(F)F | OC(c1ccccc1Cl)c1cc(Cl)ccc1NCC(F)(F)F | null | null | O1CCCC1.C(C)OCC | Reduction | Reduction of secondary amides to amines | 85b757f1833edc9e5c6365ee6b904683f414e7b9a5f9bfcfd7addca401447058 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc(Cc2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[#7:2]-[c:3])-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7]>>[F;D1;H0:5]-[C:4](-[F;D1;H0:6])(-[F;D1;H0:7])-[CH2;D2;+0:1]-[#7:2]-[c:3] | 86.7 | [{"value": 86.7, "product": "ClC=1C=CC(=C(C(C2=C(C=CC=C2)Cl)O)C1)NCC(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a suspension of 0.25 g of lithium aluminum hydride in 20 ml of absolute ethyl ether, a solution of 1.2 g of 5-chloro-α-(2-chlorophenyl)-2-(trifluoroacetylamino)benzyl alcohol in 5 ml of tetrahydrofuran was added dropwise. After mixture stirring at room temperature for 1 hour, water was added, and the organic layer w... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | c1ccccc1.c1ccccc1 | Other | O1CCCC1.C(C)OCC | null | 1 | O=C(Nc1ccc(Cl)cc1C(O)c1ccccc1Cl)C(F)(F)F>O1CCCC1.C(C)OCC>OC(c1ccccc1Cl)c1cc(Cl)ccc1NCC(F)(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-757632750487427b80394903b6f82440 | CC(C)(C)CN1C(=O)[C@@H](CC(=O)Nc2cccc(C#N)c2)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21.[N-]=[N+]=[N-]>>CC(C)(C)CN1C(=O)[C@@H](CC(=O)Nc2cccc(-c3nnn[nH]3)c2)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 | ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)(C)C)=O)CC(=O)NC2=CC(=CC=C2)C#N)C2=C(C=CC=C2)Cl)C1.[N-]=[N+]=[N-].[Na+].O>>ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)(C)C)=O)CC(=O)NC2=CC(=CC=C2)C2=NN=NN2)C2=C(C=CC=C2)Cl)C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][N:6]1[C:7](=[O:8])[C@@H:9]([CH2:10][C:11](=[O:12])[NH:13][c:14]2[cH:15][cH:16][cH:17][c:18]([C:19]#[N:20])[cH:24]2)[O:25][C@H:26]([c:27]2[cH:28][cH:29][cH:30][cH:31][c:32]2[Cl:33])[c:34]2[cH:35][c:36]([Cl:37])[cH:38][cH:39][c:40]21.[N-:21]=[N+:22]=[N-:23]>>[CH3:1][C:2]([CH3:3])([CH... | CC(C)(C)CN1C(=O)[C@@H](CC(=O)Nc2cccc(C#N)c2)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21.[N-]=[N+]=[N-] | CC(C)(C)CN1C(=O)[C@@H](CC(=O)Nc2cccc(-c3nnn[nH]3)c2)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 | null | null | CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | 237b84aaa459abf427f233dc6a07a1d9de824f980714e458423189bb68f60f12 | d8c808528b7ee68720aaeebd35cb6a2a30e344748d0066102cdae99843b93cf0 | O=C(C[C@H]1O[C@H](c2ccccc2)c2ccccc2NC1=O)Nc1cccc(-c2nnn[nH]2)c1 | [N-;H0;D1:1]=[N+;H0;D2:2]=[N-;H0;D1:3].[N;H0;D1;+0:4]#[C;H0;D2;+0:5]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:10]:[c:9]:[c;H0;D3;+0:6](-[c;H0;D3;+0:5]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:1]:[n;H0;D2;+0:2]:[nH;D2;+0:3]:1):[c:7]:[c:8] | 50.9 | [{"value": 50.9, "product": "ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)(C)C)=O)CC(=O)NC2=CC(=CC=C2)C2=NN=NN2)C2=C(C=CC=C2)Cl)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 0.2 g of trans-7-chloro-5-(2-chlorophenyl)-3-(3-cyanophenylaminocarbonylmethyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine and 80 mg of sodium azide in 5 ml of dimethylformamide was stirred at 90° C. for 60 hours. After water was added, the mixture was washed with water, after which the solven... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | null | null | c1nnn[nH]1 | c1ccccc1.c1nnn[nH]1.c1ccccc1.c1ccc2c(c1)COCC[NH]2 | null | CN(C=O)C | null | null | CC(C)(C)CN1C(=O)[C@@H](CC(=O)Nc2cccc(C#N)c2)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21.[N-]=[N+]=[N-]>CN(C=O)C>CC(C)(C)CN1C(=O)[C@@H](CC(=O)Nc2cccc(-c3nnn[nH]3)c2)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-450e99beb381497883ffdb50182f2603 | CC(C)N1C(=O)[C@@H](CC(=O)NCC#N)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21.[N-]=[N+]=[N-]>>CC(C)N1C(=O)[C@@H](CC(=O)NCc2nnn[nH]2)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 | ClC=1C=CC2=C([C@H](O[C@@H](C(N2C(C)C)=O)CC(=O)NCC#N)C2=C(C=CC=C2)Cl)C1.[N-]=[N+]=[N-].[Na+]>>ClC=1C=CC2=C([C@H](O[C@@H](C(N2C(C)C)=O)CC(=O)NCC2=NN=NN2)C2=C(C=CC=C2)Cl)C1 | [CH3:1][CH:2]([CH3:3])[N:4]1[C:5](=[O:6])[C@@H:7]([CH2:8][C:9](=[O:10])[NH:11][CH2:12][C:13]#[N:14])[O:18][C@H:19]([c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[Cl:26])[c:27]2[cH:28][c:29]([Cl:30])[cH:31][cH:32][c:33]21.[N-:15]=[N+:16]=[N-:17]>>[CH3:1][CH:2]([CH3:3])[N:4]1[C:5](=[O:6])[C@@H:7]([CH2:8][C:9](=[O:10])[NH:11]... | CC(C)N1C(=O)[C@@H](CC(=O)NCC#N)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21.[N-]=[N+]=[N-] | CC(C)N1C(=O)[C@@H](CC(=O)NCc2nnn[nH]2)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 237b84aaa459abf427f233dc6a07a1d9de824f980714e458423189bb68f60f12 | d8c808528b7ee68720aaeebd35cb6a2a30e344748d0066102cdae99843b93cf0 | O=C(C[C@H]1O[C@H](c2ccccc2)c2ccccc2NC1=O)NCc1nnn[nH]1 | [N-;H0;D1:1]=[N+;H0;D2:2]=[N-;H0;D1:3].[N;H0;D1;+0:4]#[C;H0;D2;+0:5]-[C:6]-[#7:7]-[C:8]=[O;D1;H0:9]>>[O;D1;H0:9]=[C:8]-[#7:7]-[C:6]-[c;H0;D3;+0:5]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:1]:[n;H0;D2;+0:2]:[nH;D2;+0:3]:1 | null | [] | null | null | null | null | Trans-7-chloro-5-(2-chlorophenyl)-3-(cyanomethylaminocarbonylmethyl)-1-isopropyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine and sodium azide were subjected to the same procedure as in Example 102 to yield a crystal.
Conditions: See reaction.notes.procedure_details.
Workup: to yield a crystal | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | null | null | c1nnn[nH]1 | c1nnn[nH]1.c1ccccc1.c1ccc2c(c1)COCC[NH]2 | null | null | null | null | CC(C)N1C(=O)[C@@H](CC(=O)NCC#N)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21.[N-]=[N+]=[N-]>>CC(C)N1C(=O)[C@@H](CC(=O)NCc2nnn[nH]2)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b12632ff90da4c7fbf9aead0149dd2e8 | COc1ccccc1C(=O)c1cc(Cl)ccc1N>>Nc1ccc(Cl)cc1C(=O)c1ccccc1O | NC1=C(C(=O)C2=C(C=CC=C2)OC)C=C(C=C1)Cl.C([O-])(O)=O.[Na+]>>NC1=C(C(=O)C2=C(C=CC=C2)O)C=C(C=C1)Cl | C[O:17][c:16]1[c:11]([C:9]([c:8]2[c:2]([NH2:1])[cH:3][cH:4][c:5]([Cl:6])[cH:7]2)=[O:10])[cH:12][cH:13][cH:14][cH:15]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([Cl:6])[cH:7][c:8]1[C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[OH:17] | COc1ccccc1C(=O)c1cc(Cl)ccc1N | Nc1ccc(Cl)cc1C(=O)c1ccccc1O | null | null | Br | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(c1ccccc1)c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5]=[O;D1;H0:6]>>[O;D1;H0:6]=[C:5]-[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 93.4 | [{"value": 93.4, "product": "NC1=C(C(=O)C2=C(C=CC=C2)O)C=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2.15 g of 2-amino-5-chloro-2'-methoxybenzophenone and 20 ml of 47% hydrogen bromide was heated for 1 hour under reflux. The solution was rendered neutral with sodium bicarbonate, and subjected to extraction with 100 ml of ethyl acetate. The extract solution was washed with water and dried over anhydrous ma... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccccc1 | Other | Br | null | null | COc1ccccc1C(=O)c1cc(Cl)ccc1N>Br>Nc1ccc(Cl)cc1C(=O)c1ccccc1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-64bedfb59dbe42709ee67ad4aa0bd72c | COc1ccccc1C(=O)c1cc(Cl)ccc1NC(C)=O>>Nc1ccc(Cl)cc1C(=O)c1ccccc1O | C(C)(=O)NC1=C(C(=O)C2=C(C=CC=C2)OC)C=C(C=C1)Cl.[OH-].[Na+]>>NC1=C(C(=O)C2=C(C=CC=C2)O)C=C(C=C1)Cl | CC(=O)[NH:1][c:2]1[cH:3][cH:4][c:5]([Cl:6])[cH:7][c:8]1[C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[O:17]C>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([Cl:6])[cH:7][c:8]1[C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[OH:17] | COc1ccccc1C(=O)c1cc(Cl)ccc1NC(C)=O | Nc1ccc(Cl)cc1C(=O)c1ccccc1O | null | null | Br | Reduction | OtherReaction | d3424ce4719989ec8362730265a7804ca73064ec84ab7f078c118d035fcf0f68 | 6cc30ba1c20e73143a62ef8b67c89f5e4f4048975da64c393eca7e8942cb91f2 | O=C(c1ccccc1)c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[NH;D2;+0:9]-C(-C)=O):[c:10]>>[NH2;D1;+0:9]-[c:8](:[c:10]):[c:7]-[C:5](=[O;D1;H0:6])-[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 98.1 | [{"value": 98.1, "product": "NC1=C(C(=O)C2=C(C=CC=C2)O)C=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 10 g of 2-acetylamino-5-chloro-2'-methoxybenzophenone and 100 ml of 47% hydrogen bromide was heated for 2 hours under reflux. The solution was rendered neutral with sodium hydroxide, and was subjected to extraction with 200 ml of ethyl acetate. The extract solution was washed with water and dried over anhy... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amide | Aromatic alcohol.Primary amine | null | null | c1ccccc1.c1ccccc1 | HO- | Br | null | null | COc1ccccc1C(=O)c1cc(Cl)ccc1NC(C)=O>Br>Nc1ccc(Cl)cc1C(=O)c1ccccc1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c2eabdf1be4f4a81a4b9a839ae6cea53 | BrCc1ccccc1.Nc1ccc(Cl)cc1C(=O)c1ccccc1O>>Nc1ccc(Cl)cc1C(=O)c1ccccc1OCc1ccccc1 | NC1=C(C(=O)C2=C(C=CC=C2)O)C=C(C=C1)Cl.C([O-])([O-])=O.[K+].[K+].C(C1=CC=CC=C1)Br>>NC1=C(C(=O)C2=C(C=CC=C2)OCC2=CC=CC=C2)C=C(C=C1)Cl | Br[CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1.[NH2:1][c:2]1[cH:3][cH:4][c:5]([Cl:6])[cH:7][c:8]1[C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[OH:17]>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([Cl:6])[cH:7][c:8]1[C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[O:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH... | BrCc1ccccc1.Nc1ccc(Cl)cc1C(=O)c1ccccc1O | Nc1ccc(Cl)cc1C(=O)c1ccccc1OCc1ccccc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(c1ccccc1)c1ccccc1OCc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[O;D1;H0:5]=[C:6]-[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:10] | null | [] | null | null | 2 | HOUR | In 30 ml of N,N-dimethylformamide was dissolved 5.0 g of 2-amino-5-chloro-2'-hydroxybenzophenone, as obtained in Example 123 (1), to which were added 4.2 g of potassium carbonate and 2.9 ml of benzyl bromide; the mixture was then stirred for 2 hours at room temperature. The mixture was subjected to extraction with 150 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HBr | CN(C=O)C | null | 2 | BrCc1ccccc1.Nc1ccc(Cl)cc1C(=O)c1ccccc1O>CN(C=O)C>Nc1ccc(Cl)cc1C(=O)c1ccccc1OCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-776f36934446481dab0bf262aa25a497 | CC(C)CN(C(=O)C=CC(=O)O)c1ccc(Cl)cc1C(O)c1ccccc1OCc1ccccc1>>CCOc1ccccc1C(O)c1cc(Cl)ccc1NCC(C)C | ClC1=CC(=C(C=C1)N(C(=O)C=CC(=O)O)CC(C)C)C(C1=C(C=CC=C1)OCC1=CC=CC=C1)O>>ClC=1C=CC(=C(C(C2=C(C=CC=C2)OCC)O)C1)NCC(C)C | O=C(O)C=CC(=O)[N:19]([c:18]1[c:12]([CH:10]([c:9]2[c:4]([O:3][CH2:2][c:1]3ccccc3)[cH:5][cH:6][cH:7][cH:8]2)[OH:11])[cH:13][c:14]([Cl:15])[cH:16][cH:17]1)[CH2:20][CH:21]([CH3:22])[CH3:23]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[CH:10]([OH:11])[c:12]1[cH:13][c:14]([Cl:15])[cH:16][cH:17][c:18]1[NH:19][CH2:... | CC(C)CN(C(=O)C=CC(=O)O)c1ccc(Cl)cc1C(O)c1ccccc1OCc1ccccc1 | CCOc1ccccc1C(O)c1cc(Cl)ccc1NCC(C)C | null | null | C(C)O | Reduction | OtherReaction | e461f252a26fa4b93ac220a17d32fd647954cf89489e8e27e35f099185cd9545 | 5ccb3bfdfb46dce5bb2696293a6757e412fd4dc56a89e9e787541a08ac1a1541 | c1ccc(Cc2ccccc2)cc1 | O-C(=O)-C=C-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[c:4](:[c:5]):[c:6].[#8:7]-[C:8]-[c;H0;D3;+0:9]1:c:c:c:c:c:1>>[#8:7]-[C:8]-[CH3;D1;+0:9].[C:3]-[C:2]-[NH;D2;+0:1]-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | In 150 ml of ethanol was dissolved 6.0 g of ethyl ester of 3-[N-[4-chloro-2-[2-benzyloxy-α-hydroxybenzyl]phenyl]-N-isobutylcarbamoyl]acrylic acid, as obtained in (4), to which was added 3.18 g of potassium carbonate; the mixture was then stirred overnight. The solvent was distilled off under reduced pressure, and the r... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amide | Secondary amine | c1ccccc1 | null | c1ccccc1.c1ccccc1 | HO- | C(C)O | null | null | CC(C)CN(C(=O)C=CC(=O)O)c1ccc(Cl)cc1C(O)c1ccccc1OCc1ccccc1>C(C)O>CCOc1ccccc1C(O)c1cc(Cl)ccc1NCC(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b73af90813ea458ca97a1404afcbed16 | Nc1ccc(Br)cc1-c1cccnc1C(=O)c1ncccc1-c1cc(Br)ccc1N>>Nc1ccc(Br)cc1C(O)c1ccccn1 | NC1=C(C=C(C=C1)Br)C=1C(=NC=CC1)C(=O)C1=NC=CC=C1C1=C(C=CC(=C1)Br)N.CO.[BH4-].[Na+]>>NC1=C(C(C2=NC=CC=C2)O)C=C(C=C1)Br | Nc1ccc(Br)cc1-c1cccnc1[C:9](=[O:10])[c:11]1[c:12](-[c:8]2[c:2]([NH2:1])[cH:3][cH:4][c:5]([Br:6])[cH:7]2)[cH:13][cH:14][cH:15][n:16]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([Br:6])[cH:7][c:8]1[CH:9]([OH:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][n:16]1 | Nc1ccc(Br)cc1-c1cccnc1C(=O)c1ncccc1-c1cc(Br)ccc1N | Nc1ccc(Br)cc1C(O)c1ccccn1 | null | null | null | Miscellaneous | OtherReaction | dbf8b9843a4aa59d2ff28f14ba8c3dbca059945b8b4b47a76899cf54da6edf1f | 7f88d98f489d3609ee025be1dc002fcd7725e29ffaaad7fff2cd12b3660f666b | c1ccc(Cc2ccccn2)cc1 | Br-c1:c:c:c(-N):c(-c2:c:c:c:n:c:2-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]2:[#7;a:4]:[c:5]:[c:6]:[c:7]:[c;H0;D3;+0:8]:2-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12](-[N;D1;H2:13]):[c:14]):c:1>>[N;D1;H2:13]-[c:12](:[c:14]):[c;H0;D3;+0:9](-[CH;D3;+0:1](-[OH;D1;+0:2])-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[c:7]:[cH;D2;+0:8]:1):[c:10]:[c:11] | null | [] | null | null | 30 | MINUTE | In 100 ml of methanol was dissolved 10 g of 2-amino-5-bromophenyl-2-pyridylketone. To the solution was added 1.7 g of sodium borohydride and stirred for 30 minutes. The solvent methanol was evaporated off under reduced pressure. The residue was treated with an aqueous solution of hydrochloric acid. The decomposed resid... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Primary amine | Secondary alcohol | c1ccccc1.c1ccncc1.c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | HBr | null | null | 0.5 | Nc1ccc(Br)cc1-c1cccnc1C(=O)c1ncccc1-c1cc(Br)ccc1N>>Nc1ccc(Br)cc1C(O)c1ccccn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5873d336793841adad5cbcf873b625c5 | CC(=O)O>>CC(C)(C)C=O | NC1=C(C(C2=NC=CC=C2)O)C=C(C=C1)Br.C(C)(=O)O>>NC1=C(C(C2=NC=CC=C2)O)C=C(C=C1)Br.CC(C=O)(C)C | O[C:2]([CH3:1])=[O:6]>>[CH3:1][C:2]([CH3:3])([CH3:4])[CH:5]=[O:6] | CC(=O)O | CC(C)(C)C=O | null | null | null | Functional Group Interconversion | OtherReaction | 3adc515926529d8c940a7d5ba1c36d7bcade4bebf82afc0a58508096be2f2fac | a68c8c362a41a1ec68d8543ede8c2ecdd4269a0402da828bb76b860809c088c0 | null | O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;H0;D1;+0:3]>>[C;D1;H3:2]-[C;H0;D4;+0:1](-[C;D1;H3:4])(-[C;D1;H3:5])-[C:6]=[O;H0;D1;+0:3] | null | [] | null | null | null | null | In 20 ml of acetic acid was dissolved 2.0 g of 2-amino-5-bromo-α-(2-pyridyl)benzyl alcohol obtained in (1) together with 0.86 ml of trimethylacetoaldehyde. To the solution was added 0.36 g of sodium borohydride under ice-cooling. The reaction mixture was stirred for 30 minutes at room temperature and then subjected to ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Aldehyde | null | null | null | null | null | null | null | CC(=O)O>>CC(C)(C)C=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2f947493a0ee4631a9cc6d66588aa9d1 | CCOC(=O)C[C@H]1O[C@H](c2ccccn2)c2cc(Br)ccc2N(CC(C)(C)C)C1=O>>CC(C)(C)CN1C(=O)[C@@H](CC(=O)O)O[C@H](c2ccccn2)c2cc(Br)ccc21 | BrC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)(C)C)=O)CC(=O)OCC)C2=NC=CC=C2)C1.C([O-])([O-])=O.[K+].[K+]>>BrC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)(C)C)=O)CC(=O)O)C2=NC=CC=C2)C1 | CC[O:13][C:11]([CH2:10][C@@H:9]1[C:7](=[O:8])[N:6]([CH2:5][C:2]([CH3:1])([CH3:3])[CH3:4])[c:28]2[c:22]([cH:23][c:24]([Br:25])[cH:26][cH:27]2)[C@@H:15]([c:16]2[cH:17][cH:18][cH:19][cH:20][n:21]2)[O:14]1)=[O:12]>>[CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][N:6]1[C:7](=[O:8])[C@@H:9]([CH2:10][C:11](=[O:12])[OH:13])[O:14][C@H:15... | CCOC(=O)C[C@H]1O[C@H](c2ccccn2)c2cc(Br)ccc2N(CC(C)(C)C)C1=O | CC(C)(C)CN1C(=O)[C@@H](CC(=O)O)O[C@H](c2ccccn2)c2cc(Br)ccc21 | null | null | CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1CO[C@H](c2ccccn2)c2ccccc2N1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 69.9 | [{"value": 69.9, "product": "BrC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)(C)C)=O)CC(=O)O)C2=NC=CC=C2)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In 20 ml of methanol was dissolved 1.9 g of ethyl trans-7-bromo-1-neopentyl-5-(2-pyridyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetate obtained in Example 131. To the solution was added 10 ml of an aqueous solution containing 1.1 g of potassium carbonate. The mixture was heated and refluxed for 30 minutes, and ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1.c1ccc2c(c1)COCC[NH]2 | Other | CO | null | null | CCOC(=O)C[C@H]1O[C@H](c2ccccn2)c2cc(Br)ccc2N(CC(C)(C)C)C1=O>CO>CC(C)(C)CN1C(=O)[C@@H](CC(=O)O)O[C@H](c2ccccn2)c2cc(Br)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-daf4ba5367694338ab2591f41b1c75e1 | CC(C)(C)CN1C(=O)[C@@H](CC(=O)O)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21>>CC(C)(C)CN1C(=O)[C@@H](CCO)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 | ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)(C)C)=O)CC(=O)O)C2=C(C=CC=C2)Cl)C1.CN1CCOCC1.[BH4-].[Na+].C(OCC)(=O)Cl>>ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)(C)C)=O)CCO)C2=C(C=CC=C2)Cl)C1 | O[C:11]([CH2:10][C@@H:9]1[C:7](=[O:8])[N:6]([CH2:5][C:2]([CH3:1])([CH3:3])[CH3:4])[c:28]2[c:22]([cH:23][c:24]([Cl:25])[cH:26][cH:27]2)[C@@H:14]([c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[Cl:21])[O:13]1)=[O:12]>>[CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][N:6]1[C:7](=[O:8])[C@@H:9]([CH2:10][CH2:11][OH:12])[O:13][C@H:14]([c:15... | CC(C)(C)CN1C(=O)[C@@H](CC(=O)O)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 | CC(C)(C)CN1C(=O)[C@@H](CCO)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 | null | null | CO.O1CCCC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | O=C1CO[C@H](c2ccccc2)c2ccccc2N1 | O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[C:4](-[#8:5])-[C:6](=[O;D1;H0:7])-[#7:8]>>[#7:8]-[C:6](=[O;D1;H0:7])-[C:4](-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2])-[#8:5] | 99.8 | [{"value": 99.8, "product": "ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)(C)C)=O)CCO)C2=C(C=CC=C2)Cl)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | In 200 ml of tetrahydrofuran was dissolved 14.7 g of trans-7-chloro-5-(2-chlorophenyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid obtained in Example 2 and 4.51 ml of N-methylmorpholine. To the solution was added 3.92 ml of ethyl chlorocarbonate at -10° C.; the mixture was then stirred for 15 ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1.c1ccc2c(c1)COCC[NH]2 | Other | CO.O1CCCC1 | null | 0.25 | CC(C)(C)CN1C(=O)[C@@H](CC(=O)O)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21>CO.O1CCCC1>CC(C)(C)CN1C(=O)[C@@H](CCO)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-77f2d3d356f745ffa41558ea6f3bd9f3 | CC(C)(C)CN1C(=O)[C@@H](CCO)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21>>CC(C)(C)CN1C(=O)[C@@H](CC=O)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 | ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)(C)C)=O)CCO)C2=C(C=CC=C2)Cl)C1.CS(=O)C.C(C(=O)Cl)(=O)Cl>>ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)(C)C)=O)CC=O)C2=C(C=CC=C2)Cl)C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][N:6]1[C:7](=[O:8])[C@@H:9]([CH2:10][CH2:11][OH:12])[O:13][C@H:14]([c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[Cl:21])[c:22]2[cH:23][c:24]([Cl:25])[cH:26][cH:27][c:28]21>>[CH3:1][C:2]([CH3:3])([CH3:4])[CH2:5][N:6]1[C:7](=[O:8])[C@@H:9]([CH2:10][CH:11]=[O:12])[O:13][C@H:14]([c:15]2[cH... | CC(C)(C)CN1C(=O)[C@@H](CCO)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 | CC(C)(C)CN1C(=O)[C@@H](CC=O)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 | null | null | ClCCl.O.C(C)N(CC)CC | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | O=C1CO[C@H](c2ccccc2)c2ccccc2N1 | [#7:1]-[C:2](=[O;D1;H0:3])-[C:4](-[C:5]-[CH2;D2;+0:6]-[OH;D1;+0:7])-[#8:8]>>[#7:1]-[C:2](=[O;D1;H0:3])-[C:4](-[C:5]-[CH;D2;+0:6]=[O;H0;D1;+0:7])-[#8:8] | 64.2 | [{"value": 64.2, "product": "ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)(C)C)=O)CC=O)C2=C(C=CC=C2)Cl)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To 25 ml of dichloromethane solution containing 0.70 ml of oxalyl chloride was added 5 ml of dichloromethane solution containing 0.71 ml of dimethylsulfoxide at -78° C., followed by stirring for 5 minutes. To the solution was slowly added 10 ml of dichloromethane solution containing 1.69 g of trans-7-chloro-5-(2-chloro... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1.c1ccc2c(c1)COCC[NH]2 | null | ClCCl.O.C(C)N(CC)CC | null | 0.083333 | CC(C)(C)CN1C(=O)[C@@H](CCO)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21>ClCCl.O.C(C)N(CC)CC>CC(C)(C)CN1C(=O)[C@@H](CC=O)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21 |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.