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-c31cb9b44c404c10ba3aa533aa079e2b | ord-e56469efe4574f2b8684abbf187dfa1c | CN(C(=O)CN(c1ccccc1)c1ccccc1)[C@@H]1CCN(C(=O)c2ccccc2)C1>>CN(C(=O)CN(c1ccccc1)c1ccccc1)[C@@H]1CCNC1 | C(C1=CC=CC=C1)(=O)N1C[C@@H](CC1)N(C(CN(C1=CC=CC=C1)C1=CC=CC=C1)=O)C>>C1(=CC=CC=C1)N(CC(=O)N([C@H]1CNCC1)C)C1=CC=CC=C1 | O=C(c1ccccc1)[N:22]1[CH2:21][CH2:20][C@@H:19]([N:2]([CH3:1])[C:3](=[O:4])[CH2:5][N:6]([c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:23]1>>[CH3:1][N:2]([C:3](=[O:4])[CH2:5][N:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[C@@H:19]1[CH2... | CN(C(=O)CN(c1ccccc1)c1ccccc1)[C@@H]1CCN(C(=O)c2ccccc2)C1 | CN(C(=O)CN(c1ccccc1)c1ccccc1)[C@@H]1CCNC1 | null | [Pd] | CO | Reduction | Hydrogenolysis of tertiary amines | f31a24fac1247652ffb9d16bd05f6451f460ef232d259564a837b8998ec61ef8 | 62cf08a8ae6315067a063b5b3495125ccbdaff6b2340ce1d3e1c7b6cde962ae4 | O=C(CN(c1ccccc1)c1ccccc1)N[C@@H]1CCNC1 | O=C(-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1)-c1:c:c:c:c:c:1>>[C:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:5]-1 | 114.1 | [{"value": 114.1, "product": "C1(=CC=CC=C1)N(CC(=O)N([C@H]1CNCC1)C)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of (R)—N-(1-benzoyl-pyrrolidin-3-yl)-2-diphenylamino-N-methyl-acetamide (0.68 g, 1.7 mmol) in CH3OH (30 ml) was added Pd/C 20% (170 mg). The resulting slurry was hydrogenated at 50 psi for 24 hours. The catalyst was filtered through Celite and filtrate evaporated under reduced pressure to give 0.6 g of de... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Secondary amine | c1ccccc1.C1CC[NH]C1 | C1CCNC1 | c1ccccc1.c1ccccc1.C1CCNC1 | HO- | [Pd].CO | null | 24 | CN(C(=O)CN(c1ccccc1)c1ccccc1)[C@@H]1CCN(C(=O)c2ccccc2)C1>[Pd].CO>CN(C(=O)CN(c1ccccc1)c1ccccc1)[C@@H]1CCNC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-85194727a3bc4855a7dda35f5106f763 | BrC(c1ccccc1)c1ccccc1.CN(C(=O)CN(c1ccccc1)c1ccccc1)[C@@H]1CCNC1>>CN(C(=O)CN(c1ccccc1)c1ccccc1)[C@@H]1CCN(C(c2ccccc2)c2ccccc2)C1 | BrC(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)N(CC(=O)N([C@H]1CNCC1)C)C1=CC=CC=C1.C(=O)([O-])[O-].[K+].[K+]>>C(C1=CC=CC=C1)(C1=CC=CC=C1)N1C[C@@H](CC1)N(C(CN(C1=CC=CC=C1)C1=CC=CC=C1)=O)C | Br[CH:23]([c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1)[c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1.[CH3:1][N:2]([C:3](=[O:4])[CH2:5][N:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[C@@H:19]1[CH2:20][CH2:21][NH:22][CH2:36]1>>[CH3:1][N:2]([C:3](=[O:4])[CH2:5][N:6]([c:7]1[cH:8][cH... | BrC(c1ccccc1)c1ccccc1.CN(C(=O)CN(c1ccccc1)c1ccccc1)[C@@H]1CCNC1 | CN(C(=O)CN(c1ccccc1)c1ccccc1)[C@@H]1CCN(C(c2ccccc2)c2ccccc2)C1 | null | null | CC(CC)=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 10cc789bcfe0ae11c7b2b474c79d3cdda850354ad720004a77dedb66c0fbd515 | fb63ba09935e18320be03869002f6d5d0f0321fe7dbcd94a5ae956c3effd182d | O=C(CN(c1ccccc1)c1ccccc1)N[C@@H]1CCN(C(c2ccccc2)c2ccccc2)C1 | Br-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7].[C:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-1>>[c:3]:[c:2](-[CH;D3;+0:1](-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[C:8]-[C:12]-1)-[c:5](:[c:6]):[c:7]):[c:4] | null | [] | null | null | null | null | To a solution of bromodiphenylmethane (0.3 g, 1.23 mmol) in butanone (10 ml) was added (R)-2-diphenylamino-N-methyl-N-pyrrolidin-3-yl-acetamide (0.46 g, 1.5 mmol), K2CO3 (0.17 g, 1.23 mmol) and KI (0.2 g, 1.23 mmol). The mixture was heated under reflux for 18 hours, then filtered and the solvent was removed in vacuo. T... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.c1ccccc1.C1CC[NH]C1.c1ccccc1.c1ccccc1 | HBr | CC(CC)=O | null | null | BrC(c1ccccc1)c1ccccc1.CN(C(=O)CN(c1ccccc1)c1ccccc1)[C@@H]1CCNC1>CC(CC)=O>CN(C(=O)CN(c1ccccc1)c1ccccc1)[C@@H]1CCN(C(c2ccccc2)c2ccccc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b9d361fa95a640f9a04b086442faf109 | CN[C@@H]1CCN(C(=O)c2ccccc2)C1.O=C(CBr)N(c1ccccc1)c1ccccc1>>O=C(CNC[C@H]1CCN(Cc2ccccc2)C1)N(c1ccccc1)c1ccccc1 | C(C1=CC=CC=C1)(=O)N1C[C@@H](CC1)NC.BrCC(=O)N(C1=CC=CC=C1)C1=CC=CC=C1.C(=O)(O)[O-].[Na+].CC#N>>C(C1=CC=CC=C1)N1C[C@H](CC1)CNCC(=O)N(C1=CC=CC=C1)C1=CC=CC=C1 | O=[C:10]([N:9]1[CH2:8][CH2:7][C@@H:6]([NH:4][CH3:5])[CH2:17]1)[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.Br[CH2:3][C:2](=[O:1])[N:18]([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1>>[O:1]=[C:2]([CH2:3][NH:4][CH2:5][C@H:6]1[CH2:7][CH2:8][N:9]([CH2:10][c:11]2[cH:12][cH:13][cH:14]... | CN[C@@H]1CCN(C(=O)c2ccccc2)C1.O=C(CBr)N(c1ccccc1)c1ccccc1 | O=C(CNC[C@H]1CCN(Cc2ccccc2)C1)N(c1ccccc1)c1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c66894eac9ef615d3b141f01122e8f9823ff344d499c205c62c1b3cf49e74ba3 | 378c54a7d08ff33f29940783d7d340c21eaa54954287ff0d36ce8b1eb86b6057 | O=C(CNC[C@H]1CCN(Cc2ccccc2)C1)N(c1ccccc1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[c:5])-[c:6].O=[C;H0;D3;+0:7](-[#7:8]1-[C:9]-[C@H;D3;+0:10](-[NH;D2;+0:11]-[CH3;D1;+0:12])-[C:13]-[C:14]-1)-[c:15](:[c:16]):[c:17]>>[O;D1;H0:3]=[C:2](-[CH2;D2;+0:1]-[NH;D2;+0:11]-[CH2;D2;+0:12]-[C@@H;D3;+0:10]1-[C:9]-[#7:8](-[CH2;D2;+0:7]-[c:15](:[c:16]):[c:17])-[C:14]-[C:13... | null | [] | null | null | null | null | To a solution of (R)-(1-benzoyl-pyrrolidin-3-yl)-methyl-amine(0.32 g, 1.68 mmol) in dry CH3CN (10 ml) was added 2-bromo-N,N-diphenyl acetamide(0.49 g, 1.68 mmol) and NaHCO3 (0.28 g, 3.36 mmol) under nitrogen. The reaction mixture was refluxed overnight. After cooling, the solvent was evaporated. The residue was taken u... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amide.Secondary amine | Secondary amine | C1CC[NH]C1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1.c1ccccc1.c1ccccc1 | Br- | null | null | null | CN[C@@H]1CCN(C(=O)c2ccccc2)C1.O=C(CBr)N(c1ccccc1)c1ccccc1>>O=C(CNC[C@H]1CCN(Cc2ccccc2)C1)N(c1ccccc1)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a1bf7b07a6e84b91be3f4ef0d347f994 | CN(CC(=O)N(c1ccccc1)c1ccccc1)[C@@H]1CCN(C(=O)c2ccccc2)C1>>CN(CC(=O)N(c1ccccc1)c1ccccc1)[C@@H]1CCNC1 | C(C1=CC=CC=C1)(=O)N1C[C@@H](CC1)N(CC(=O)N(C1=CC=CC=C1)C1=CC=CC=C1)C>>CN(CC(=O)N(C1=CC=CC=C1)C1=CC=CC=C1)[C@H]1CNCC1 | O=C(c1ccccc1)[N:22]1[CH2:21][CH2:20][C@@H:19]([N:2]([CH3:1])[CH2:3][C:4](=[O:5])[N:6]([c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:23]1>>[CH3:1][N:2]([CH2:3][C:4](=[O:5])[N:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[C@@H:19]1[CH2... | CN(CC(=O)N(c1ccccc1)c1ccccc1)[C@@H]1CCN(C(=O)c2ccccc2)C1 | CN(CC(=O)N(c1ccccc1)c1ccccc1)[C@@H]1CCNC1 | null | [Pd] | CO | Reduction | Hydrogenolysis of tertiary amines | f31a24fac1247652ffb9d16bd05f6451f460ef232d259564a837b8998ec61ef8 | 62cf08a8ae6315067a063b5b3495125ccbdaff6b2340ce1d3e1c7b6cde962ae4 | O=C(CN[C@@H]1CCNC1)N(c1ccccc1)c1ccccc1 | O=C(-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1)-c1:c:c:c:c:c:1>>[C:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:5]-1 | 95.1 | [{"value": 95.1, "product": "CN(CC(=O)N(C1=CC=CC=C1)C1=CC=CC=C1)[C@H]1CNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of (R)-2-[(1-benzoyl-pyrrolidin-3-yl)-methyl-amino]-N,N-diphenyl acetamide(0.68 g, 1.70 mmol) in CH3OH (30 ml) was added Pd/C 20% (170 mg). The resulting slurry was hydrogenated at 50 psi for 24 hours. The catalyst was filtered through Celite and filtrate evaporated under reduced pressure to give 0.5 g of... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Secondary amine | c1ccccc1.C1CC[NH]C1 | C1CCNC1 | c1ccccc1.c1ccccc1.C1CCNC1 | HO- | [Pd].CO | null | 24 | CN(CC(=O)N(c1ccccc1)c1ccccc1)[C@@H]1CCN(C(=O)c2ccccc2)C1>[Pd].CO>CN(CC(=O)N(c1ccccc1)c1ccccc1)[C@@H]1CCNC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bdf3f775b9a54da7b287838161695a5b | BrC(c1ccccc1)c1ccccc1.CN(CC(=O)N(c1ccccc1)c1ccccc1)[C@@H]1CCNC1>>CN(CC(=O)N(c1ccccc1)c1ccccc1)[C@@H]1CCN(C(c2ccccc2)c2ccccc2)C1 | BrC(C1=CC=CC=C1)C1=CC=CC=C1.CN(CC(=O)N(C1=CC=CC=C1)C1=CC=CC=C1)[C@H]1CNCC1.C(=O)([O-])[O-].[K+].[K+]>>C(C1=CC=CC=C1)(C1=CC=CC=C1)N1C[C@@H](CC1)N(CC(=O)N(C1=CC=CC=C1)C1=CC=CC=C1)C | Br[CH:23]([c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1)[c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1.[CH3:1][N:2]([CH2:3][C:4](=[O:5])[N:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[C@@H:19]1[CH2:20][CH2:21][NH:22][CH2:36]1>>[CH3:1][N:2]([CH2:3][C:4](=[O:5])[N:6]([c:7]1[cH:8][cH... | BrC(c1ccccc1)c1ccccc1.CN(CC(=O)N(c1ccccc1)c1ccccc1)[C@@H]1CCNC1 | CN(CC(=O)N(c1ccccc1)c1ccccc1)[C@@H]1CCN(C(c2ccccc2)c2ccccc2)C1 | null | null | CC(CC)=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 10cc789bcfe0ae11c7b2b474c79d3cdda850354ad720004a77dedb66c0fbd515 | fb63ba09935e18320be03869002f6d5d0f0321fe7dbcd94a5ae956c3effd182d | O=C(CN[C@@H]1CCN(C(c2ccccc2)c2ccccc2)C1)N(c1ccccc1)c1ccccc1 | Br-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7].[C:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-1>>[c:3]:[c:2](-[CH;D3;+0:1](-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[C:8]-[C:12]-1)-[c:5](:[c:6]):[c:7]):[c:4] | null | [] | null | null | null | null | To a solution of bromodiphenylmethane (0.33 g, 1.34 mmol) in butanone (10 ml) was added (R)-2-(methyl-pyrrolidin-3-yl-amino)-N,N-diphenyl acetamide(0.5 g, 1.61 mmol), K2CO3 (0.18 g, 1.34 mmol) and KI (0.22 g, 1.34 mmol). The mixture was, heated under reflux for 18 hours, then filtered and the solvent was removed in vac... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.c1ccccc1.C1CC[NH]C1.c1ccccc1.c1ccccc1 | HBr | CC(CC)=O | null | null | BrC(c1ccccc1)c1ccccc1.CN(CC(=O)N(c1ccccc1)c1ccccc1)[C@@H]1CCNC1>CC(CC)=O>CN(CC(=O)N(c1ccccc1)c1ccccc1)[C@@H]1CCN(C(c2ccccc2)c2ccccc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-822d7d076ac1463281ca632d166946dc | CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(=O)O.CCO>>CCOC(=O)[C@@H]1C[C@@H](O)CN1C(=O)OC(C)(C)C | C1CCC(CC1)N=C=NC2CCCCC2.C(C)(C)(C)OC(=O)N1[C@H](C(=O)O)C[C@H](C1)O.C(C)O>>CCOC(=O)[C@H]1N(C[C@@H](C1)O)C(=O)OC(C)(C)C | O[C:4](=[O:5])[C@@H:6]1[CH2:7][C@@H:8]([OH:9])[CH2:10][N:11]1[C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18].[CH3:1][CH2:2][OH:3]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C@@H:6]1[CH2:7][C@@H:8]([OH:9])[CH2:10][N:11]1[C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18] | CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(=O)O.CCO | CCOC(=O)[C@@H]1C[C@@H](O)CN1C(=O)OC(C)(C)C | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | C1CCNC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C:13].[C;D1;H3:14]-[C:15]-[OH;D1;+0:16]>>[C:13]-[#7:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:16]-[C:1... | 173.5 | [{"value": 173.5, "product": "CCOC(=O)[C@H]1N(C[C@@H](C1)O)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of (4R)-(tert-Butoxycarbonyl)-4-hydroxy-L-proline (26) (0.92 g, 4.0 mmol) in dry CH2Cl2 (30 ml) was added ethanol (1 ml, 21 mmol). To the reaction was added DCC (1.64 g, 8.0 mmol) and DMAP (cat) and the reaction mixture was, stirred under nitrogen at room temperature overnight. The reaction was then conce... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | C1CC[NH]C1 | HO- | CN(C)C=1C=CN=CC1.C(Cl)Cl | null | 8 | CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(=O)O.CCO>CN(C)C=1C=CN=CC1.C(Cl)Cl>CCOC(=O)[C@@H]1C[C@@H](O)CN1C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5dc719d2fa02420b85b134fb57840152 | CCOC(=O)[C@@H]1C[C@@H](O)CN1C(=O)OC(C)(C)C.Cc1ccc(S(=O)(=O)Cl)cc1>>CCOC(=O)[C@@H]1C[C@@H](OS(=O)(=O)c2ccc(C)cc2)CN1C(=O)OC(C)(C)C | CCOC(=O)[C@H]1N(C[C@@H](C1)O)C(=O)OC(C)(C)C.C1(=CC=C(C=C1)S(=O)(=O)Cl)C>>CCOC(=O)[C@H]1N(C[C@@H](C1)OS(=O)(=O)C1=CC=C(C=C1)C)C(=O)OC(C)(C)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C@@H:6]1[CH2:7][C@@H:8]([OH:9])[CH2:20][N:21]1[C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28].Cl[S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][c:16]([CH3:17])[cH:18][cH:19]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C@@H:6]1[CH2:7][C@@H:8]([O:9][S:10](=[O:11])(=[O:12])[c:13]2[cH:14][cH:1... | CCOC(=O)[C@@H]1C[C@@H](O)CN1C(=O)OC(C)(C)C.Cc1ccc(S(=O)(=O)Cl)cc1 | CCOC(=O)[C@@H]1C[C@@H](OS(=O)(=O)c2ccc(C)cc2)CN1C(=O)OC(C)(C)C | null | null | N1=CC=CC=C1 | Acylation | Formation of Sulfonic Esters | ad3deb6f5d4dc7823aa3ad2bfe24985be1f3e6860ff8cc0ba215d7624074ef69 | ec645297cfd3107bffb1a4753ac125e48856598e58005e939bb2f0e91bf5e57c | O=S(=O)(O[C@@H]1CCNC1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[#7:7]-[C:8]-[C:9](-[OH;D1;+0:10])-[C:11]>>[#7:7]-[C:8]-[C:9](-[O;H0;D2;+0:10]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6])-[C:11] | 89.8 | [{"value": 89.8, "product": "CCOC(=O)[C@H]1N(C[C@@H](C1)OS(=O)(=O)C1=CC=C(C=C1)C)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | To the solution of (2S,4R)-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid-1-tert-butyl ester-2-ethyl ester (27) (1.8 g, 7 mmol) in dry pyridine (40 ml) was added p-toluenesulfonyl chloride (4.0 g, 21 mmol) under nitrogen at 0° C. The reaction mixture was kept refrigerated at 0° C. for 2 days. The reaction was then concent... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Secondary alcohol.Sulfonyl halide | Tosylate | null | null | C1CC[NH]C1.c1ccccc1 | HCl | N1=CC=CC=C1 | null | 48 | CCOC(=O)[C@@H]1C[C@@H](O)CN1C(=O)OC(C)(C)C.Cc1ccc(S(=O)(=O)Cl)cc1>N1=CC=CC=C1>CCOC(=O)[C@@H]1C[C@@H](OS(=O)(=O)c2ccc(C)cc2)CN1C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8f69ce2be3a64ab4ba0c5693a2c95f75 | CCOC(=O)[C@@H]1C[C@@H](OS(=O)(=O)c2ccc(C)cc2)CN1C(=O)OC(C)(C)C.[N-]=[N+]=[N-]>>CCOC(=O)[C@@H]1C[C@H](N=[N+]=[N-])CN1C(=O)OC(C)(C)C | CCOC(=O)[C@H]1N(C[C@@H](C1)OS(=O)(=O)C1=CC=C(C=C1)C)C(=O)OC(C)(C)C.[N-]=[N+]=[N-].[Na+]>>CCOC(=O)[C@H]1N(C[C@H](C1)N=[N+]=[N-])C(=O)OC(C)(C)C | Cc1ccc(S(=O)(=O)O[C@@H:8]2[CH2:7][C@@H:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:12]2)cc1.[N-:9]=[N+:10]=[N-:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C@@H:6]1[CH2:7][C@H:8]([N:9]=[N+:10]=[N-:11])[CH2:12][N:13]1[C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3... | CCOC(=O)[C@@H]1C[C@@H](OS(=O)(=O)c2ccc(C)cc2)CN1C(=O)OC(C)(C)C.[N-]=[N+]=[N-] | CCOC(=O)[C@@H]1C[C@H](N=[N+]=[N-])CN1C(=O)OC(C)(C)C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | cf780355dc56581e8d37046459aa1a19ddbf607b31eb6c95196e260e01e63476 | 6961229e10e0db3c410e97098a5b94923cb09bb1c069f267ae4410afd98cc24e | C1CCNC1 | C-c1:c:c:c(-S(=O)(=O)-O-[C@H;D3;+0:1]2-[C:2]-[#7:3](-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10])-[C:11](-[C:12](-[#8:13])=[O;D1;H0:14])-[C:15]-2):c:c:1.[N-;H0;D1:16]=[#7;+:17]=[N;-;D1;H0:18]>>[#8:13]-[C:12](=[O;D1;H0:14])-[C:11]1-[C:15]-[C@H;D3;+0:1](-[N;H0;D2;+0:16]=[#7;+:17]=[N;-;D1;H0:... | null | [] | null | null | 8 | HOUR | To the solution of (2S,4R)-4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid-1-tert-butyl ester-2-ethyl ester) (28) (2.6 g, 6.3 mmol) in dry DMF (15 ml) was added NaN3 (0.41 g, 6.3 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was then concentrated under reduced p... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate | Azide | c1ccccc1.C1CC[NH]C1 | C1CC[NH]C1 | C1CC[NH]C1 | TsOH.HO- | CN(C)C=O | null | 8 | CCOC(=O)[C@@H]1C[C@@H](OS(=O)(=O)c2ccc(C)cc2)CN1C(=O)OC(C)(C)C.[N-]=[N+]=[N-]>CN(C)C=O>CCOC(=O)[C@@H]1C[C@H](N=[N+]=[N-])CN1C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0eb52d540c8643569b4e14c25cf6b4c8 | CCOC(=O)[C@@H]1C[C@H](N=[N+]=[N-])CN1C(=O)OC(C)(C)C>>CCOC(=O)[C@@H]1C[C@H](N)CN1C(=O)OC(C)(C)C | CCOC(=O)[C@H]1N(C[C@H](C1)N=[N+]=[N-])C(=O)OC(C)(C)C>>CCOC(=O)[C@H]1N(C[C@H](C1)N)C(=O)OC(C)(C)C | [N-]=[N+]=[N:9][C@H:8]1[CH2:7][C@@H:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:10]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C@@H:6]1[CH2:7][C@H:8]([NH2:9])[CH2:10][N:11]1[C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18] | CCOC(=O)[C@@H]1C[C@H](N=[N+]=[N-])CN1C(=O)OC(C)(C)C | CCOC(=O)[C@@H]1C[C@H](N)CN1C(=O)OC(C)(C)C | null | [Pd] | CO | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | C1CCNC1 | [#7:1]-[C:2]-[C:3](-[N;H0;D2;+0:4]=[N+]=[N-])-[C:5]>>[#7:1]-[C:2]-[C:3](-[NH2;D1;+0:4])-[C:5] | 175.1 | [{"value": 175.1, "product": "CCOC(=O)[C@H]1N(C[C@H](C1)N)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To the solution of (2S,4S)-4-azido-pyrrolidin-1,2-dicarboxylic acid-1-tert-butyl ester-2-ethyl ester (29) (1.8 g, 2.1 mmol) in CH3OH (40 ml) was added Pd/C 10% (50 mg). The resulting slurry was hydrogenated at 1 atm for 24 hours. The catalyst was filtered through Celite and filtrate evaporated under reduced pressure to... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | C1CC[NH]C1 | Other | [Pd].CO | null | 24 | CCOC(=O)[C@@H]1C[C@H](N=[N+]=[N-])CN1C(=O)OC(C)(C)C>[Pd].CO>CCOC(=O)[C@@H]1C[C@H](N)CN1C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a777f1168cba4253ad0ab4561a06139a | CCOC(=O)[C@@H]1C[C@H](NC(=O)CCCCC(c2ccc(F)cc2)c2ccc(F)cc2)CN1.COc1c(C(C)(C)C)cc(C(=O)O)cc1C(C)(C)C>>CCOC(=O)[C@@H]1C[C@H](NC(=O)CCCCC(c2ccc(F)cc2)c2ccc(F)cc2)CN1C(=O)c1cc(C(C)(C)C)c(OC)c(C(C)(C)C)c1 | C(CCl)Cl.C(C)OC(=O)[C@H]1NC[C@H](C1)NC(CCCCC(C1=CC=C(C=C1)F)C1=CC=C(C=C1)F)=O.C(C)(C)(C)C=1C=C(C(=O)O)C=C(C1OC)C(C)(C)C>>C(C)OC(=O)[C@H]1N(C[C@H](C1)NC(CCCCC(C1=CC=C(C=C1)F)C1=CC=C(C=C1)F)=O)C(C1=CC(=C(C(=C1)C(C)(C)C)OC)C(C)(C)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C@@H:6]1[CH2:7][C@H:8]([NH:9][C:10](=[O:11])[CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([c:17]2[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]2)[c:24]2[cH:25][cH:26][c:27]([F:28])[cH:29][cH:30]2)[CH2:31][NH:32]1.O[C:33](=[O:34])[c:35]1[cH:36][c:37]([C:38]([CH3:39])([CH3:40])[CH3:41])[c:42]([O:43... | CCOC(=O)[C@@H]1C[C@H](NC(=O)CCCCC(c2ccc(F)cc2)c2ccc(F)cc2)CN1.COc1c(C(C)(C)C)cc(C(=O)O)cc1C(C)(C)C | CCOC(=O)[C@@H]1C[C@H](NC(=O)CCCCC(c2ccc(F)cc2)c2ccc(F)cc2)CN1C(=O)c1cc(C(C)(C)C)c(OC)c(C(C)(C)C)c1 | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | a590d96426a2fbaed42913d9daf8a16471a16de4978200f1d35a30a10009ebe7 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(CCCCC(c1ccccc1)c1ccccc1)N[C@H]1CCN(C(=O)c2ccccc2)C1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C:10]1-[C:11]-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C:10]1-[C:11]-[C:12]-[C:13]-[N;H0;D3;+0:14]-1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 75.7 | [{"value": 75.7, "product": "C(C)OC(=O)[C@H]1N(C[C@H](C1)NC(CCCCC(C1=CC=C(C=C1)F)C1=CC=C(C=C1)F)=O)C(C1=CC(=C(C(=C1)C(C)(C)C)OC)C(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To the solution of (2S,4S)-4-[6,6-Bis-(4-fluoro-phenyl)-hexanoylamino]-pyrrolidine-2-carboxylic acid ethyl ester (32) (0.39 g, 0.88 mmol) in dry CH2Cl2 (20 ml) was added 3,5-di-tert-butyl-4-methoxy benzoic acid (0.23 g, 0.88 mmol). To the reaction was added EDC (0.34 g, 1.76 mmol) and DMAP (cat), and the reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | CN(C)C=1C=CN=CC1.C(Cl)Cl | null | 8 | CCOC(=O)[C@@H]1C[C@H](NC(=O)CCCCC(c2ccc(F)cc2)c2ccc(F)cc2)CN1.COc1c(C(C)(C)C)cc(C(=O)O)cc1C(C)(C)C>CN(C)C=1C=CN=CC1.C(Cl)Cl>CCOC(=O)[C@@H]1C[C@H](NC(=O)CCCCC(c2ccc(F)cc2)c2ccc(F)cc2)CN1C(=O)c1cc(C(C)(C)C)c(OC)c(C(C)(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7f009c52032d459bb8dea3aedafca017 | CCOC(=O)[C@@H]1C[C@H](NC(=O)CCCCC(c2ccc(F)cc2)c2ccc(F)cc2)CN1C(=O)c1cc(C(C)(C)C)c(OC)c(C(C)(C)C)c1>>COc1c(C(C)(C)C)cc(C(=O)N2C[C@@H](NC(=O)CCCCC(c3ccc(F)cc3)c3ccc(F)cc3)C[C@H]2C(=O)O)cc1C(C)(C)C | C(C)OC(=O)[C@H]1N(C[C@H](C1)NC(CCCCC(C1=CC=C(C=C1)F)C1=CC=C(C=C1)F)=O)C(C1=CC(=C(C(=C1)C(C)(C)C)OC)C(C)(C)C)=O.[Li+].[OH-]>>FC1=CC=C(C=C1)C(CCCCC(=O)N[C@H]1C[C@H](N(C1)C(C1=CC(=C(C(=C1)C(C)(C)C)OC)C(C)(C)C)=O)C(=O)O)C1=CC=C(C=C1)F | CC[O:42][C:40]([C@H:39]1[N:13]([C:11]([c:10]2[cH:9][c:4]([C:5]([CH3:6])([CH3:7])[CH3:8])[c:3]([O:2][CH3:1])[c:44]([C:45]([CH3:46])([CH3:47])[CH3:48])[cH:43]2)=[O:12])[CH2:14][C@@H:15]([NH:16][C:17](=[O:18])[CH2:19][CH2:20][CH2:21][CH2:22][CH:23]([c:24]2[cH:25][cH:26][c:27]([F:28])[cH:29][cH:30]2)[c:31]2[cH:32][cH:33][c... | CCOC(=O)[C@@H]1C[C@H](NC(=O)CCCCC(c2ccc(F)cc2)c2ccc(F)cc2)CN1C(=O)c1cc(C(C)(C)C)c(OC)c(C(C)(C)C)c1 | COc1c(C(C)(C)C)cc(C(=O)N2C[C@@H](NC(=O)CCCCC(c3ccc(F)cc3)c3ccc(F)cc3)C[C@H]2C(=O)O)cc1C(C)(C)C | null | null | O.CO.C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(CCCCC(c1ccccc1)c1ccccc1)N[C@H]1CCN(C(=O)c2ccccc2)C1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7:5]>>[#7:5]-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 75.4 | [{"value": 75.4, "product": "FC1=CC=C(C=C1)C(CCCCC(=O)N[C@H]1C[C@H](N(C1)C(C1=CC(=C(C(=C1)C(C)(C)C)OC)C(C)(C)C)=O)C(=O)O)C1=CC=C(C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To the solution of (2S,4S)-4-[6,6-Bis-(4-fluoro-phenyl)-hexanoylamino]-1-(3,5-di-tert-butyl-4-methoxy-benzoyl)-pyrrolidine-2-carboxylic acid ethyl ester (33) (0.32 g, 0.52 mmol) in THF (15 ml), MeOH (5 ml) and water (5 ml) was added LiOH (0.1 g, 2.45 mmol), and the reaction mixture was stirred at room temperature overn... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.C1CC[NH]C1.c1ccccc1.c1ccccc1 | Other | O.CO.C1CCOC1 | null | 8 | CCOC(=O)[C@@H]1C[C@H](NC(=O)CCCCC(c2ccc(F)cc2)c2ccc(F)cc2)CN1C(=O)c1cc(C(C)(C)C)c(OC)c(C(C)(C)C)c1>O.CO.C1CCOC1>COc1c(C(C)(C)C)cc(C(=O)N2C[C@@H](NC(=O)CCCCC(c3ccc(F)cc3)c3ccc(F)cc3)C[C@H]2C(=O)O)cc1C(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bac9ddbcb8d04a9bba676089661f1a08 | BrC(c1ccccc1)c1ccccc1.CCOC(=O)[C@@H]1C[C@H](NC(=O)CC(c2ccccc2)c2ccccc2)CN1>>CCOC(=O)[C@@H]1C[C@H](NC(=O)CC(c2ccccc2)c2ccccc2)CN1C(c1ccccc1)c1ccccc1 | BrC(C1=CC=CC=C1)C1=CC=CC=C1.C(C)OC(=O)[C@H]1NC[C@H](C1)NC(CC(C1=CC=CC=C1)C1=CC=CC=C1)=O.C(=O)([O-])[O-].[K+].[K+]>>C(C)OC(=O)[C@H]1N(C[C@H](C1)NC(CC(C1=CC=CC=C1)C1=CC=CC=C1)=O)C(C1=CC=CC=C1)C1=CC=CC=C1 | Br[CH:28]([c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1)[c:35]1[cH:36][cH:37][cH:38][cH:39][cH:40]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[C@@H:6]1[CH2:7][C@H:8]([NH:9][C:10](=[O:11])[CH2:12][CH:13]([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26][NH:27]1>>[CH3:1][CH2:2][O:3][C:4... | BrC(c1ccccc1)c1ccccc1.CCOC(=O)[C@@H]1C[C@H](NC(=O)CC(c2ccccc2)c2ccccc2)CN1 | CCOC(=O)[C@@H]1C[C@H](NC(=O)CC(c2ccccc2)c2ccccc2)CN1C(c1ccccc1)c1ccccc1 | null | null | CC(CC)=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 10cc789bcfe0ae11c7b2b474c79d3cdda850354ad720004a77dedb66c0fbd515 | fb63ba09935e18320be03869002f6d5d0f0321fe7dbcd94a5ae956c3effd182d | O=C(CC(c1ccccc1)c1ccccc1)N[C@H]1CCN(C(c2ccccc2)c2ccccc2)C1 | Br-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7].[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[C:12]1-[C:13]-[C:14]-[C:15]-[NH;D2;+0:16]-1>>[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[C:12]1-[C:13]-[C:14]-[C:15]-[N;H0;D3;+0:16]-1-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7] | 57.2 | [{"value": 57.2, "product": "C(C)OC(=O)[C@H]1N(C[C@H](C1)NC(CC(C1=CC=CC=C1)C1=CC=CC=C1)=O)C(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of bromodiphenylmethane (0.4 g, 1.64 mmol) in butanone (10 ml) was added (2S,4S)-4-(3,3-diphenyl-propionylamino)-pyrrolidine-2-carboxylic acid ethyl ester (36) (0.6 g, 1.64 mmol), K2CO3 (0.23 g, 1.64 mmol) and KI (0.27 g, 1.64 mmol). The mixture was heated under reflux for 18 hours, and then filtered and ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HBr | CC(CC)=O | null | null | BrC(c1ccccc1)c1ccccc1.CCOC(=O)[C@@H]1C[C@H](NC(=O)CC(c2ccccc2)c2ccccc2)CN1>CC(CC)=O>CCOC(=O)[C@@H]1C[C@H](NC(=O)CC(c2ccccc2)c2ccccc2)CN1C(c1ccccc1)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-796be2c3ca244a2cbb9c89a0b40f9d1a | CCOC(=O)[C@@H]1C[C@H](NC(=O)CC(c2ccccc2)c2ccccc2)CN1C(c1ccccc1)c1ccccc1>>O=C(CC(c1ccccc1)c1ccccc1)N[C@H]1C[C@@H](C(=O)O)N(C(c2ccccc2)c2ccccc2)C1 | C(C)OC(=O)[C@H]1N(C[C@H](C1)NC(CC(C1=CC=CC=C1)C1=CC=CC=C1)=O)C(C1=CC=CC=C1)C1=CC=CC=C1.[Li+].[OH-]>>C(C1=CC=CC=C1)(C1=CC=CC=C1)N1[C@@H](C[C@@H](C1)NC(CC(C1=CC=CC=C1)C1=CC=CC=C1)=O)C(=O)O | CC[O:23][C:21]([C@@H:20]1[CH2:19][C@H:18]([NH:17][C:2](=[O:1])[CH2:3][CH:4]([c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:38][N:24]1[CH:25]([c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1)[c:32]1[cH:33][cH:34][cH:35][cH:36][cH:37]1)=[O:22]>>[O:1]=[C:2]([CH2:3][CH:4]([c:5]1[cH:6][cH... | CCOC(=O)[C@@H]1C[C@H](NC(=O)CC(c2ccccc2)c2ccccc2)CN1C(c1ccccc1)c1ccccc1 | O=C(CC(c1ccccc1)c1ccccc1)N[C@H]1C[C@@H](C(=O)O)N(C(c2ccccc2)c2ccccc2)C1 | null | null | O.CO.C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(CC(c1ccccc1)c1ccccc1)N[C@H]1CCN(C(c2ccccc2)c2ccccc2)C1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7:5]>>[#7:5]-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 47.6 | [{"value": 47.6, "product": "C(C1=CC=CC=C1)(C1=CC=CC=C1)N1[C@@H](C[C@@H](C1)NC(CC(C1=CC=CC=C1)C1=CC=CC=C1)=O)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To the solution of (2S,4S)-1-benzhydryl-4-(3,3-diphenyl-propionylamino)-pyrrolidine-2-carboxylic acid ethyl ester (37) (0.25 g, 0.5 mmol) in THF (15 ml), MeOH (5 ml) and water (5 ml) was added LiOH (0.1 g, 2.45 mmol), and the reaction mixture was stirred at room temperature overnight. The reaction was then concentrated... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.C1CC[NH]C1.c1ccccc1.c1ccccc1 | Other | O.CO.C1CCOC1 | null | 8 | CCOC(=O)[C@@H]1C[C@H](NC(=O)CC(c2ccccc2)c2ccccc2)CN1C(c1ccccc1)c1ccccc1>O.CO.C1CCOC1>O=C(CC(c1ccccc1)c1ccccc1)N[C@H]1C[C@@H](C(=O)O)N(C(c2ccccc2)c2ccccc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-13e9753f36934bee8bf2fae8a1e16e7b | CC(C)(C)OC(=O)NC1CCN(C(c2ccccc2)c2ccccc2)C1=O>>NC1CCN(C(c2ccccc2)c2ccccc2)C1=O | C(C)(C)(C)OC(NC1C(N(CC1)C(C1=CC=CC=C1)C1=CC=CC=C1)=O)=O.C(F)(F)(F)C(=O)O>>NC1C(N(CC1)C(C1=CC=CC=C1)C1=CC=CC=C1)=O | CC(C)(C)OC(=O)[NH:1][CH:2]1[CH2:3][CH2:4][N:5]([CH:6]([c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[C:19]1=[O:20]>>[NH2:1][CH:2]1[CH2:3][CH2:4][N:5]([CH:6]([c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[C:19]1=[O:20] | CC(C)(C)OC(=O)NC1CCN(C(c2ccccc2)c2ccccc2)C1=O | NC1CCN(C(c2ccccc2)c2ccccc2)C1=O | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C1CCCN1C(c1ccccc1)c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]1-[C:3]-[C:4]-[#7:5](-[C:6])-[C:7]-1=[O;D1;H0:8]>>[C:6]-[#7:5]1-[C:4]-[C:3]-[C:2](-[NH2;D1;+0:1])-[C:7]-1=[O;D1;H0:8] | 97 | [{"value": 97.0, "product": "NC1C(N(CC1)C(C1=CC=CC=C1)C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To the solution of (1-benzhydryl-2-oxo-pyrrollidin-3-yl)-carbamic acid tert-butyl ester (41) (1.2 g, 3.26 mmol) in CH2Cl2 (20 ml) was added CF3CO2H (8 ml). The resulting mixture was stirred under nitrogen at room temperature overnight. The reaction was then concentrated under reduced pressure. The residue was dissolved... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1CC[NH]C1.c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl | null | 8 | CC(C)(C)OC(=O)NC1CCN(C(c2ccccc2)c2ccccc2)C1=O>C(Cl)Cl>NC1CCN(C(c2ccccc2)c2ccccc2)C1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c05a6af839be4448b137432d6475a7b3 | NC1CCN(C(c2ccccc2)c2ccccc2)C1=O.O=C(O)CC(c1ccccc1)c1ccccc1>>O=C(CC(c1ccccc1)c1ccccc1)NC1CCN(C(c2ccccc2)c2ccccc2)C1=O | C(CCl)Cl.NC1C(N(CC1)C(C1=CC=CC=C1)C1=CC=CC=C1)=O.C1(=CC=CC=C1)C(CC(=O)O)C1=CC=CC=C1>>C(C1=CC=CC=C1)(C1=CC=CC=C1)N1C(C(CC1)NC(CC(C1=CC=CC=C1)C1=CC=CC=C1)=O)=O | [NH2:17][CH:18]1[CH2:19][CH2:20][N:21]([CH:22]([c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[c:29]2[cH:30][cH:31][cH:32][cH:33][cH:34]2)[C:35]1=[O:36].O[C:2](=[O:1])[CH2:3][CH:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[O:1]=[C:2]([CH2:3][CH:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][c... | NC1CCN(C(c2ccccc2)c2ccccc2)C1=O.O=C(O)CC(c1ccccc1)c1ccccc1 | O=C(CC(c1ccccc1)c1ccccc1)NC1CCN(C(c2ccccc2)c2ccccc2)C1=O | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CC(c1ccccc1)c1ccccc1)NC1CCN(C(c2ccccc2)c2ccccc2)C1=O | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[#7:6]1-[C:7]-[C:8]-[C:9](-[NH2;D1;+0:10])-[C:11]-1=[O;D1;H0:12]>>[C:5]-[#7:6]1-[C:7]-[C:8]-[C:9](-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4])-[C:11]-1=[O;D1;H0:12] | 70 | [{"value": 70.0, "product": "C(C1=CC=CC=C1)(C1=CC=CC=C1)N1C(C(CC1)NC(CC(C1=CC=CC=C1)C1=CC=CC=C1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 3-amino-1-benzhydryl-pyrrolidin-2-one (42) (0.2 g, 0.75 mmol) in dry CH2Cl2 (20 ml)was added 3,3-diphenylpropionic acid (0.19 g, 0.82 mmol) under nitrogen. To the reaction was added EDC (0.18 g, 0.9 mmol) and DMAP (cat), and the reaction mixture was stirred under nitrogen at room temperature overnight.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.C1CC[NH]C1.c1ccccc1.c1ccccc1 | HO- | CN(C)C=1C=CN=CC1.C(Cl)Cl | null | 8 | NC1CCN(C(c2ccccc2)c2ccccc2)C1=O.O=C(O)CC(c1ccccc1)c1ccccc1>CN(C)C=1C=CN=CC1.C(Cl)Cl>O=C(CC(c1ccccc1)c1ccccc1)NC1CCN(C(c2ccccc2)c2ccccc2)C1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-90252da0f3144d0e85fb42da01f4d4d5 | NC1CCN(C(c2ccccc2)c2ccccc2)C1=O.O=C=NC(c1ccccc1)c1ccccc1>>O=C(NC1CCN(C(c2ccccc2)c2ccccc2)C1=O)NC(c1ccccc1)c1ccccc1 | NC1C(N(CC1)C(C1=CC=CC=C1)C1=CC=CC=C1)=O.C1(=CC=CC=C1)C(C1=CC=CC=C1)N=C=O>>C(C1=CC=CC=C1)(C1=CC=CC=C1)NC(=O)NC1C(N(CC1)C(C1=CC=CC=C1)C1=CC=CC=C1)=O | [NH2:3][CH:4]1[CH2:5][CH2:6][N:7]([CH:8]([c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[C:21]1=[O:22].[O:1]=[C:2]=[N:23][CH:24]([c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1)[c:31]1[cH:32][cH:33][cH:34][cH:35][cH:36]1>>[O:1]=[C:2]([NH:3][CH:4]1[CH2:5][CH2:6][N:7]([CH:8]([c:9]2[cH:... | NC1CCN(C(c2ccccc2)c2ccccc2)C1=O.O=C=NC(c1ccccc1)c1ccccc1 | O=C(NC1CCN(C(c2ccccc2)c2ccccc2)C1=O)NC(c1ccccc1)c1ccccc1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NC1CCN(C(c2ccccc2)c2ccccc2)C1=O)NC(c1ccccc1)c1ccccc1 | [C:1]-[#7:2]1-[C:3]-[C:4]-[C:5](-[NH2;D1;+0:6])-[C:7]-1=[O;D1;H0:8].[O;D1;H0:9]=[C;H0;D2;+0:10]=[N;H0;D2;+0:11]-[C:12](-[c:13])-[c:14]>>[C:1]-[#7:2]1-[C:3]-[C:4]-[C:5](-[NH;D2;+0:6]-[C;H0;D3;+0:10](=[O;D1;H0:9])-[NH;D2;+0:11]-[C:12](-[c:13])-[c:14])-[C:7]-1=[O;D1;H0:8] | 65 | [{"value": 65.0, "product": "C(C1=CC=CC=C1)(C1=CC=CC=C1)NC(=O)NC1C(N(CC1)C(C1=CC=CC=C1)C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | To a solution of 3-amino-1-benzhydryl-pyrrolidin-2-one (42) (0.2 g, 0.75 mmol) in dry CH2Cl2 (15 ml) was added diphenylmethyl isocyanate (0.17 mg, 0.82 mmol) dropwise under nitrogen. The resulting mixture was stirred at room temperature for two days followed by refluxing for 5 hours. Removal of solvent under reduced pr... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | C1CC[NH]C1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | C(Cl)Cl | null | 48 | NC1CCN(C(c2ccccc2)c2ccccc2)C1=O.O=C=NC(c1ccccc1)c1ccccc1>C(Cl)Cl>O=C(NC1CCN(C(c2ccccc2)c2ccccc2)C1=O)NC(c1ccccc1)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-14563a3db8c14122aafee18220f7b5df | NC1CCN(C(c2ccccc2)c2ccccc2)C1=O.O=C(O)CN(c1ccccc1)c1ccccc1>>O=C(CN(c1ccccc1)c1ccccc1)NC1CCN(C(c2ccccc2)c2ccccc2)C1=O | C(CCl)Cl.NC1C(N(CC1)C(C1=CC=CC=C1)C1=CC=CC=C1)=O.C1(=CC=CC=C1)N(C1=CC=CC=C1)CC(=O)O>>C(C1=CC=CC=C1)(C1=CC=CC=C1)N1C(C(CC1)NC(CN(C1=CC=CC=C1)C1=CC=CC=C1)=O)=O | [NH2:17][CH:18]1[CH2:19][CH2:20][N:21]([CH:22]([c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[c:29]2[cH:30][cH:31][cH:32][cH:33][cH:34]2)[C:35]1=[O:36].O[C:2](=[O:1])[CH2:3][N:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[O:1]=[C:2]([CH2:3][N:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:... | NC1CCN(C(c2ccccc2)c2ccccc2)C1=O.O=C(O)CN(c1ccccc1)c1ccccc1 | O=C(CN(c1ccccc1)c1ccccc1)NC1CCN(C(c2ccccc2)c2ccccc2)C1=O | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CN(c1ccccc1)c1ccccc1)NC1CCN(C(c2ccccc2)c2ccccc2)C1=O | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4].[C:5]-[#7:6]1-[C:7]-[C:8]-[C:9](-[NH2;D1;+0:10])-[C:11]-1=[O;D1;H0:12]>>[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[C:9]1-[C:8]-[C:7]-[#7:6](-[C:5])-[C:11]-1=[O;D1;H0:12] | 69 | [{"value": 69.0, "product": "C(C1=CC=CC=C1)(C1=CC=CC=C1)N1C(C(CC1)NC(CN(C1=CC=CC=C1)C1=CC=CC=C1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 3-amino-1-benzhydryl-pyrrolidin-2-one (42) (0.2 g, 0.75 mmol) in dry CH2Cl2 (20 ml)was added diphenylamino ethanoic acid (0.19 g, 0.82 mmol) under nitrogen. To the reaction was added EDC (0.18 g, 0.9 mmol) and DMAP (cat) and the reaction mixture was stirred under nitrogen at room temperature overnight.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.C1CC[NH]C1.c1ccccc1.c1ccccc1 | HO- | CN(C)C=1C=CN=CC1.C(Cl)Cl | null | 8 | NC1CCN(C(c2ccccc2)c2ccccc2)C1=O.O=C(O)CN(c1ccccc1)c1ccccc1>CN(C)C=1C=CN=CC1.C(Cl)Cl>O=C(CN(c1ccccc1)c1ccccc1)NC1CCN(C(c2ccccc2)c2ccccc2)C1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f49a2e9c3a4b49999eae65a12fbe610b | NC1CCN(C(c2ccccc2)c2ccccc2)C1=O.O=C(CBr)N(c1ccccc1)c1ccccc1>>O=C(CNC1CCN(C(c2ccccc2)c2ccccc2)C1=O)N(c1ccccc1)c1ccccc1 | NC1C(N(CC1)C(C1=CC=CC=C1)C1=CC=CC=C1)=O.BrCC(=O)N(C1=CC=CC=C1)C1=CC=CC=C1.[H-].[Na+]>>C(C1=CC=CC=C1)(C1=CC=CC=C1)N1C(C(CC1)NCC(=O)N(C1=CC=CC=C1)C1=CC=CC=C1)=O | [NH2:4][CH:5]1[CH2:6][CH2:7][N:8]([CH:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[C:22]1=[O:23].Br[CH2:3][C:2](=[O:1])[N:24]([c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1)[c:31]1[cH:32][cH:33][cH:34][cH:35][cH:36]1>>[O:1]=[C:2]([CH2:3][NH:4][CH:5]1[CH2:6][CH2:7][N:8]([CH:9]... | NC1CCN(C(c2ccccc2)c2ccccc2)C1=O.O=C(CBr)N(c1ccccc1)c1ccccc1 | O=C(CNC1CCN(C(c2ccccc2)c2ccccc2)C1=O)N(c1ccccc1)c1ccccc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | O=C(CNC1CCN(C(c2ccccc2)c2ccccc2)C1=O)N(c1ccccc1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[c:5])-[c:6].[C:7]-[#7:8]1-[C:9]-[C:10]-[C:11](-[NH2;D1;+0:12])-[C:13]-1=[O;D1;H0:14]>>[C:7]-[#7:8]1-[C:9]-[C:10]-[C:11](-[NH;D2;+0:12]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[c:5])-[c:6])-[C:13]-1=[O;D1;H0:14] | 73 | [{"value": 73.0, "product": "C(C1=CC=CC=C1)(C1=CC=CC=C1)N1C(C(CC1)NCC(=O)N(C1=CC=CC=C1)C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3-amino-1-benzhydryl-pyrrolidin-2-one (42) (0.2 g, 0.75 mmol in dry DMF (15 ml) was added 2-bromo-N,N-diphenyl acetamide (0.24 g, 0.82 mmol) and NaH (50 mg) under nitrogen. The reaction mixture was heated at 100 degrees overnight. After cooling, the solvent was evaporated and residue was taken up with ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | C1CC[NH]C1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | null | null | NC1CCN(C(c2ccccc2)c2ccccc2)C1=O.O=C(CBr)N(c1ccccc1)c1ccccc1>CN(C)C=O>O=C(CNC1CCN(C(c2ccccc2)c2ccccc2)C1=O)N(c1ccccc1)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e83a7c5d5f0b4d529f6aaf0097ae6224 | COc1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(-c2ccc(OCc3cc(C(=O)NS(=O)(=O)c4ccccc4)oc3C)cc2)cc1 | COC1=CC=C(C=C1)C1=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)O.Cl.CN(CCCN=C=NCC)C.C1(=CC=CC=C1)S(=O)(=O)N>>COC1=CC=C(C=C1)C1=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)NS(=O)(=O)C1=CC=CC=C1 | O[C:16]([c:15]1[cH:14][c:13]([CH2:12][O:11][c:10]2[cH:9][cH:8][c:7](-[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:34][cH:33]3)[cH:32][cH:31]2)[c:29]([CH3:30])[o:28]1)=[O:17].[NH2:18][S:19](=[O:20])(=[O:21])[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([O:11][CH2:... | COc1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)cc1.NS(=O)(=O)c1ccccc1 | COc1ccc(-c2ccc(OCc3cc(C(=O)NS(=O)(=O)c4ccccc4)oc3C)cc2)cc1 | null | CN(C)C1=CC=NC=C1 | ClCCl | Acylation | Carboxylic acid with primary amine to amide | 195a412a8235704efe2985cdc18467ba661e632bab7b61944399ecc813e32a09 | 5e4665bad9c6f58dddd98c5f95e436c640b4c0118b04efea5cd58c7d1755401d | O=C(NS(=O)(=O)c1ccccc1)c1cc(COc2ccc(-c3ccccc3)cc2)co1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[NH2;D1;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[c:3](:[c:4]):[#8;a:5]:[c:6] | 8.5 | [{"value": 8.5, "product": "COC1=CC=C(C=C1)C1=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)NS(=O)(=O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred solution of 4-(4′-methoxy-biphenyl-4-yloxymethyl)-5-methyl-furan-2-carboxylic acid (4) (250 mg) in dichloromethane (50 mL) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (142 mg), 4-(N,N-dimethylamino)pyridine (2 mg) and benzenesulfonamide (232 mg). After 16 hours the reaction mi... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Carboxylic acid | Sulfonamide.Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccoc1.c1ccccc1 | HO- | CN(C)C1=CC=NC=C1.ClCCl | null | null | COc1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)cc1.NS(=O)(=O)c1ccccc1>CN(C)C1=CC=NC=C1.ClCCl>COc1ccc(-c2ccc(OCc3cc(C(=O)NS(=O)(=O)c4ccccc4)oc3C)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-14da1013d149444fadc18cb28ff0aae9 | CC(C)(C)OC(=O)NCc1ccc(S(N)(=O)=O)cc1.COc1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)cc1>>COc1ccc(-c2ccc(OCc3cc(C(=O)NS(=O)(=O)c4ccc(CN)cc4)oc3C)cc2)cc1 | COC1=CC=C(C=C1)C1=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)O.C(C)(C)(C)OC(NCC1=CC=C(C=C1)S(N)(=O)=O)=O.C(N)(OC(C)(C)C)=O.FC(C(=O)O)(F)F.ClCCl>>FC(C(=O)O)(F)F.NCC1=CC=C(C=C1)S(=O)(=O)NC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)C1=CC=C(C=C1)OC)C | CC(C)(C)OC(=O)[NH:27][CH2:26][c:25]1[cH:24][cH:23][c:22]([S:19]([NH2:18])(=[O:20])=[O:21])[cH:29][cH:28]1.O[C:16]([c:15]1[cH:14][c:13]([CH2:12][O:11][c:10]2[cH:9][cH:8][c:7](-[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:36][cH:35]3)[cH:34][cH:33]2)[c:31]([CH3:32])[o:30]1)=[O:17]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2... | CC(C)(C)OC(=O)NCc1ccc(S(N)(=O)=O)cc1.COc1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)cc1 | COc1ccc(-c2ccc(OCc3cc(C(=O)NS(=O)(=O)c4ccc(CN)cc4)oc3C)cc2)cc1 | null | null | null | Acylation | OtherReaction | a760ca44badae53cef3a44d9b0c4e8bf45a42ef421ec54275506cdd614b80a67 | 840e1f09c3507b8ae193cb274981cf3e3bee243853f088474eb17d6f0eb72564 | O=C(NS(=O)(=O)c1ccccc1)c1cc(COc2ccc(-c3ccccc3)cc2)co1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[c:3].[NH2;D1;+0:4]-[#16:5](=[O;D1;H0:6])(=[O;D1;H0:7])-[c:8].O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[#8;a:13]:[c:14]>>[NH2;D1;+0:1]-[C:2]-[c:3].[O;D1;H0:10]=[C;H0;D3;+0:9](-[NH;D2;+0:4]-[#16:5](=[O;D1;H0:6])(=[O;D1;H0:7])-[c:8])-[c:11](:[c:12]):[#8;a:13]:[c:14] | null | [] | null | null | null | null | 4-(4′-Methoxy-biphenyl-4-yloxymethyl)-5-methyl-furan-2-carboxylic acid (4) (50 mg) was reacted with (4-sulphamoyl-benzyl)-carbamic acid tert-butyl ester (85 mg) in an analogous manner to that described in Example 2A. The intermediate tert-butyl carbamate was hydrolysed with 1% trifluoroacetic acid/dichloromethane over ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Carbamic ester.Carboxylic acid.Ether.Boc | Sulfonamide.Secondary amide.Primary amine | null | null | c1ccccc1.c1ccccc1.c1ccoc1.c1ccccc1 | HO- | null | null | null | CC(C)(C)OC(=O)NCc1ccc(S(N)(=O)=O)cc1.COc1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)cc1>>COc1ccc(-c2ccc(OCc3cc(C(=O)NS(=O)(=O)c4ccc(CN)cc4)oc3C)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cda13cc1515e4528b0f71e0e93e8c05c | CC(=O)Oc1ccc(S(N)(=O)=O)cc1.COc1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)cc1>>COc1ccc(-c2ccc(OCc3cc(C(=O)NS(=O)(=O)c4ccc(O)cc4)oc3C)cc2)cc1 | C[O-].[Na+].COC1=CC=C(C=C1)C1=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)O.S(N)(=O)(=O)C1=CC=C(C=C1)OC(C)=O>>OC1=CC=C(C=C1)S(=O)(=O)NC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)C1=CC=C(C=C1)OC)C | CC(=O)[O:26][c:25]1[cH:24][cH:23][c:22]([S:19]([NH2:18])(=[O:20])=[O:21])[cH:28][cH:27]1.O[C:16]([c:15]1[cH:14][c:13]([CH2:12][O:11][c:10]2[cH:9][cH:8][c:7](-[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:35][cH:34]3)[cH:33][cH:32]2)[c:30]([CH3:31])[o:29]1)=[O:17]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10... | CC(=O)Oc1ccc(S(N)(=O)=O)cc1.COc1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)cc1 | COc1ccc(-c2ccc(OCc3cc(C(=O)NS(=O)(=O)c4ccc(O)cc4)oc3C)cc2)cc1 | null | null | O.CO | Acylation | OtherReaction | ccf63ed2558f3e347d41fcbfdfe7add29165cbb3f81591cb16bdfafb45c4bfd8 | 97f370026ca06570a9ea0c7cfeec3690633e89955cf72b7ca0b6e4c204c30702 | O=C(NS(=O)(=O)c1ccccc1)c1cc(COc2ccc(-c3ccccc3)cc2)co1 | C-C(=O)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[#16:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[c:9].O-[C;H0;D3;+0:10](=[O;D1;H0:11])-[c:12](:[c:13]):[#8;a:14]:[c:15]>>[O;D1;H0:11]=[C;H0;D3;+0:10](-[NH;D2;+0:5]-[#16:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[c:9])-[c:12](:[c:13]):[#8;a:14]:[c:15].[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 20.6 | [{"value": 20.6, "product": "OC1=CC=C(C=C1)S(=O)(=O)NC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)C1=CC=C(C=C1)OC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-(4′-Methoxy-biphenyl-4-yloxymethyl)-5-methyl-furan-2-carboxylic acid (4) (50 mg) was reacted with acetic acid 4-sulphamoyl-phenyl ester (64 mg) in an analogous manner to that described in Example 2A. The acetic ester intermediate was hydrolysed with sodium methoxide (80 mg) in a mixture of methanol (10 mL) and water ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Carboxylic acid.Ester | Sulfonamide.Secondary amide.Aromatic alcohol | null | null | c1ccccc1.c1ccccc1.c1ccoc1.c1ccccc1 | HO- | O.CO | null | null | CC(=O)Oc1ccc(S(N)(=O)=O)cc1.COc1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)cc1>O.CO>COc1ccc(-c2ccc(OCc3cc(C(=O)NS(=O)(=O)c4ccc(O)cc4)oc3C)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dd218db336c3408d83fea32600257830 | COC(=O)Cl.Cc1occc1CO[Si](C(C)C)(C(C)C)C(C)C>>COC(=O)c1cc(CO[Si](C(C)C)(C(C)C)C(C)C)c(C)o1 | [Cl-].[NH4+].C(C)(CC)[Li].C(C)(C)[Si](OCC1=C(OC=C1)C)(C(C)C)C(C)C.ClC(=O)OC>>COC(=O)C=1OC(=C(C1)CO[Si](C(C)C)(C(C)C)C(C)C)C | Cl[C:3]([O:2][CH3:1])=[O:4].[cH:5]1[cH:6][c:7]([CH2:8][O:9][Si:10]([CH:11]([CH3:12])[CH3:13])([CH:14]([CH3:15])[CH3:16])[CH:17]([CH3:18])[CH3:19])[c:20]([CH3:21])[o:22]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][O:9][Si:10]([CH:11]([CH3:12])[CH3:13])([CH:14]([CH3:15])[CH3:16])[CH:17]([CH3:18])[CH3:19])[c:20](... | COC(=O)Cl.Cc1occc1CO[Si](C(C)C)(C(C)C)C(C)C | COC(=O)c1cc(CO[Si](C(C)C)(C(C)C)C(C)C)c(C)o1 | null | null | O1CCCC1 | C-C Coupling | Friedel-Crafts acylation | 1c39f06f701be9363365d1994407a43ecc223155f8d909b9c19badfc90d9f29d | 25d9bd8621b941df428c033fedc648334f6dc6f4157dff30f33212e6bac7f1de | c1ccoc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[#8;a:5]1:[c:6]:[c:7]:[c:8]:[cH;D2;+0:9]:1>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:9]1:[#8;a:5]:[c:6]:[c:7]:[c:8]:1 | null | [] | null | null | 1 | HOUR | A solution of triisopropyl-(2-methyl-furan-3-ylmethoxy)-silane (14) (10.0 g) in tetrahydrofuran (300 mL) was cooled to −78° C. with stirring was treated drop-wise with sec-butyllithium (3.0 M in cyclohexane, 37 mL). After 1 hour the reaction mixture was treated drop-wise with a solution of methyl chloroformate (5.2 g) ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether | Ester | c1ccoc1 | c1ccoc1 | c1ccoc1 | HCl | O1CCCC1 | null | 1 | COC(=O)Cl.Cc1occc1CO[Si](C(C)C)(C(C)C)C(C)C>O1CCCC1>COC(=O)c1cc(CO[Si](C(C)C)(C(C)C)C(C)C)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ac2ef776a5ec4e41aedf2abf920d3586 | COC(=O)c1cc(CO[Si](C(C)C)(C(C)C)C(C)C)c(C)o1>>COC(=O)c1cc(CO)c(C)o1 | COC(=O)C=1OC(=C(C1)CO[Si](C(C)C)(C(C)C)C(C)C)C.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>COC(=O)C=1OC(=C(C1)CO)C | CC(C)[Si](C(C)C)(C(C)C)[O:9][CH2:8][c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[o:12][c:10]1[CH3:11]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][OH:9])[c:10]([CH3:11])[o:12]1 | COC(=O)c1cc(CO[Si](C(C)C)(C(C)C)C(C)C)c(C)o1 | COC(=O)c1cc(CO)c(C)o1 | null | null | O1CCCC1 | Deprotection | Alcohol deprotection from silyl ethers | 488547c1043a845c08188be7baa01e2ee1f8d7661927552d481c2d214b18b6c0 | 5c02ee98cb6b210a313993bea9e102110eb73637a50746f5457590f98613069b | c1ccoc1 | C-C(-C)-[Si](-[O;H0;D2;+0:1]-[C:2]-[c:3]:[c:4]:[#8;a:5])(-C(-C)-C)-C(-C)-C>>[#8;a:5]:[c:4]:[c:3]-[C:2]-[OH;D1;+0:1] | null | [] | null | null | 16 | HOUR | A stirred solution of 5-methyl-4-triisopropylsilanyloxymethyl-furan-2-carboxylic acid methyl ester (15) (5.2 g) in tetrahydrofuran (200 mL) was treated with tetrabutylammonium fluoride (1.0 M solution in tetrahydrofuran, 3.2 mL) and stirring continued for 16 hours. The reaction mixture was concentrated in vacuo and the... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Primary alcohol | null | null | c1ccoc1 | Other | O1CCCC1 | null | 16 | COC(=O)c1cc(CO[Si](C(C)C)(C(C)C)C(C)C)c(C)o1>O1CCCC1>COC(=O)c1cc(CO)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a7d0d0205801432b8fa8e525235e33f4 | COC(=O)c1cc(CO)c(C)o1.Oc1ccc(-c2ccccc2)cc1>>COC(=O)c1cc(COc2ccc(-c3ccccc3)cc2)c(C)o1 | OC1=CC=C(C=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.COC(=O)C=1OC(=C(C1)CO)C.OC1=CC=C(C=C1)C1=CC=CC=C1>>COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)C1=CC=CC=C1)C | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][OH:9])[c:22]([CH3:23])[o:24]1.O[c:10]1[cH:11][cH:12][c:13](-[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:20][cH:21]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][O:9][c:10]2[cH:11][cH:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[cH:20][cH:21]2)[c:2... | COC(=O)c1cc(CO)c(C)o1.Oc1ccc(-c2ccccc2)cc1 | COC(=O)c1cc(COc2ccc(-c3ccccc3)cc2)c(C)o1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 8915084acbaaf997bf0f89ff5187cb2f89c25dc683fffc57b3391298c8430dd9 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(-c2ccc(OCc3ccoc3)cc2)cc1 | O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8;a:6]:[c:7]:[c:8]-[C:9]-[OH;D1;+0:10]>>[#8;a:6]:[c:7]:[c:8]-[C:9]-[O;H0;D2;+0:10]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | 0 | CELSIUS | 10 | MINUTE | A solution of 4-hydroxymethyl-5-methyl-furan-2-carboxylic acid methyl ester (16) (1 g) in anhydrous tetrahydrofuran (20 mL) was cooled to 0° C. under a nitrogen atmosphere. 4-Hydroxybiphenyl (3 g) and triphenylphosphine (4.61 g) were added and the mixture was treated with di-isopropylazodicarboxylate (3.46 mL) dropwise... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccoc1.c1ccccc1.c1ccccc1 | HO- | O1CCCC1 | 0 | 0.166667 | COC(=O)c1cc(CO)c(C)o1.Oc1ccc(-c2ccccc2)cc1>O1CCCC1>COC(=O)c1cc(COc2ccc(-c3ccccc3)cc2)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d25e81af639241ea95fb0a8d026f08b5 | COC(=O)c1cc(COc2ccc(-c3ccccc3)cc2)c(C)o1>>Cc1oc(C(=O)O)cc1COc1ccc(-c2ccccc2)cc1 | [OH-].[Li+].COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)C1=CC=CC=C1)C>>C1(=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)O)C1=CC=CC=C1 | C[O:7][C:5]([c:4]1[o:3][c:2]([CH3:1])[c:9]([CH2:10][O:11][c:12]2[cH:13][cH:14][c:15](-[c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[cH:22][cH:23]2)[cH:8]1)=[O:6]>>[CH3:1][c:2]1[o:3][c:4]([C:5](=[O:6])[OH:7])[cH:8][c:9]1[CH2:10][O:11][c:12]1[cH:13][cH:14][c:15](-[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[cH:22][cH:23]1 | COC(=O)c1cc(COc2ccc(-c3ccccc3)cc2)c(C)o1 | Cc1oc(C(=O)O)cc1COc1ccc(-c2ccccc2)cc1 | null | null | O1CCCC1.CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ccc(OCc3ccoc3)cc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#8;a:5]>>[#8;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 22 | [{"value": 22.0, "product": "C1(=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | 1M Aqueous lithium hydroxide (18 mL) was added to solution of 4-(biphenyl-4-yloxymethyl)-5-methyl-furan-2-carboxylic acid methyl ester (17) (1 g) in tetrahydrofuran/methanol (2:1 by volume, 100 mL) and the mixture stirred at room temperature for 5 h. The solvent was removed in vacuo, the residue dissolved in water (20 ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccoc1.c1ccccc1.c1ccccc1 | Other | O1CCCC1.CO | null | 5 | COC(=O)c1cc(COc2ccc(-c3ccccc3)cc2)c(C)o1>O1CCCC1.CO>Cc1oc(C(=O)O)cc1COc1ccc(-c2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1f48ae5b0846442abf06d18edea5ee6e | COC(=O)c1cc(CO)c(C)o1.Oc1ccc(I)cc1>>COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1 | COC(=O)C=1OC(=C(C1)CO)C.IC1=CC=C(C=C1)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.CC(C)OC(=O)/N=N/C(=O)OC(C)C>>COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)I)C | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][OH:9])[c:17]([CH3:18])[o:19]1.O[c:10]1[cH:11][cH:12][c:13]([I:14])[cH:15][cH:16]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][O:9][c:10]2[cH:11][cH:12][c:13]([I:14])[cH:15][cH:16]2)[c:17]([CH3:18])[o:19]1 | COC(=O)c1cc(CO)c(C)o1.Oc1ccc(I)cc1 | COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 8915084acbaaf997bf0f89ff5187cb2f89c25dc683fffc57b3391298c8430dd9 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(OCc2ccoc2)cc1 | O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8;a:6]:[c:7]:[c:8]-[C:9]-[OH;D1;+0:10]>>[#8;a:6]:[c:7]:[c:8]-[C:9]-[O;H0;D2;+0:10]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 63.4 | [{"value": 63.4, "product": "COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)I)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-hydroxymethyl-5-methyl-furan-2-carboxylic acid methyl ester (16) (1.14 g) in tetrahydrofuran (15 mL) was cooled to 0° C. with stirring and treated with 4-iodophenol (4.6 g), triphenylphosphine (5.5 g) and diisopropylazodicarboxylate (4.2 g). After 10 minutes the cooling bath was removed. After 3 hours t... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccoc1.c1ccccc1 | HO- | O1CCCC1 | null | null | COC(=O)c1cc(CO)c(C)o1.Oc1ccc(I)cc1>O1CCCC1>COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a3ea5e46e05a4ac28b7ebc9fb4b6d5dc | CC(=O)c1ccc(B(O)O)cc1.COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1>>CC(=O)c1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)cc1 | COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)I)C.C(C)(=O)C1=CC=C(C=C1)B(O)O.CN(C=O)C.C(C)(=O)[O-].[K+]>>C(C)(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)O | OB(O)[c:7]1[cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:26][cH:25]1.C[O:19][C:17]([c:16]1[cH:15][c:14]([CH2:13][O:12][c:11]2[cH:10][cH:9][c:8](I)[cH:24][cH:23]2)[c:21]([CH3:22])[o:20]1)=[O:18]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([O:12][CH2:13][c:14]3[cH:15][c:16]([C:17](=[O:18])[OH:19]... | CC(=O)c1ccc(B(O)O)cc1.COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1 | CC(=O)c1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)cc1 | null | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2] | ClCCl | C-C Coupling | OtherReaction | 04157bef51d5543c035526858b11d2af2b78e75d38cd85edf56b617e6aebc946 | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2ccc(OCc3ccoc3)cc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#8;a:5].I-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10].O-B(-O)-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]>>[#8;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1].[c:10]:[c:9]:[c;H0;D3;+0:6](-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]):[c:7]:[c:8] | 20.4 | [{"value": 20.4, "product": "C(C)(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 16 | HOUR | A stirred mixture of 4-(4-iodo-phenoxymethyl)-5-methyl-furan-2-carboxylic acid methyl ester (20) (0.26 g), 4-acetylphenylboronic acid (0.15 g), N,N-dimethylformamide (30 mL), potassium acetate (0.26 g) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (40 mg) was heated... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccoc1 | HI.B | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].ClCCl | 90 | 16 | CC(=O)c1ccc(B(O)O)cc1.COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1>C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].ClCCl>CC(=O)c1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-df684f31504c41af9b9ddc8343cecf7c | COC(=O)c1cc(CO)c(C)o1>>COC(=O)c1cc(C(=O)O)c(C)o1 | CC(=O)C.OS(=O)(=O)O.O=[Cr](=O)=O.COC(=O)C=1OC(=C(C1)CO)C>>COC(=O)C=1OC(=C(C1)C(=O)O)C | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][OH:10])[c:11]([CH3:12])[o:13]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([C:8](=[O:9])[OH:10])[c:11]([CH3:12])[o:13]1 | COC(=O)c1cc(CO)c(C)o1 | COC(=O)c1cc(C(=O)O)c(C)o1 | null | null | CC(=O)C.C(C)OCC | Oxidation | Oxidation of alcohol to carboxylic acid | b709baac44a995a9a8f6386a6b5d87f98c32eb5a0636340abc1f778fae827230 | 4454822e22dc2dc24e7495385256bfce456e337c240bb764261f81dbeda1aaa1 | c1ccoc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[#8;a:5]:[c:6](-[C;D1;H3:7]):[c:8](-[CH2;D2;+0:9]-[O;D1;H1:10]):[c:11]:1>>[#8:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[#8;a:5]:[c:6](-[C;D1;H3:7]):[c:8](-[C;H0;D3;+0:9](=[O;D1;H0:12])-[O;D1;H1:10]):[c:11]:1 | null | [] | null | null | 5 | HOUR | Jones' reagent (Prepared according to Fieser and Fieser, Reagents for Organic Synthesis, Volume 1, page 142, 1967) was added drop-wise to a stirred solution of 4-hydroxymethyl-5-methyl-furan-2-carboxylic acid methyl ester (16) (100 mg) in acetone (10 mL) until the orange colouration just remained. Stirring was continue... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Carboxylic acid | null | null | c1ccoc1 | Other | CC(=O)C.C(C)OCC | null | 5 | COC(=O)c1cc(CO)c(C)o1>CC(=O)C.C(C)OCC>COC(=O)c1cc(C(=O)O)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-05d5003fdcd942298997f09dcba031a1 | COC(=O)c1cc(C(=O)O)c(C)o1.COc1ccc(-c2ccc(N)cc2)cc1>>COc1ccc(-c2ccc(NC(=O)c3cc(C(=O)O)oc3C)cc2)cc1 | COC(=O)C=1OC(=C(C1)C(=O)O)C.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1N=CC=C2)OC(=[N+](C)C)N(C)C.C(C)(C)N(CC)C(C)C.COC1=CC=C(C=C1)C1=CC=C(C=C1)N>>COC1=CC=C(C=C1)C1=CC=C(C=C1)NC(=O)C=1C=C(OC1C)C(=O)O | C[O:19][C:17]([c:16]1[cH:15][c:14]([C:12](O)=[O:13])[c:21]([CH3:22])[o:20]1)=[O:18].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([NH2:11])[cH:23][cH:24]2)[cH:25][cH:26]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([NH:11][C:12](=[O:13])[c:14]3[cH:15][c:16]([C:17](=[O:18])[OH:19])[o:2... | COC(=O)c1cc(C(=O)O)c(C)o1.COc1ccc(-c2ccc(N)cc2)cc1 | COc1ccc(-c2ccc(NC(=O)c3cc(C(=O)O)oc3C)cc2)cc1 | null | null | CN(C=O)C.C(C)(=O)OCC | Acylation | OtherReaction | 2f4be8b14ede2d52c920d439e5f741d97aa4249f4c57807152c62994aca84307 | 87a69d5ad38be49e96448ab38c6e7071a2232ada5542b6b62a2f1e1b1e6e076f | O=C(Nc1ccc(-c2ccccc2)cc1)c1ccoc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[#8;a:5]:[c:6](-[C;D1;H3:7]):[c:8](-[C;H0;D3;+0:9](-O)=[O;D1;H0:10]):[c:11]:1.[NH2;D1;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H3:7]-[c:6]1:[#8;a:5]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[c:11]:[c:8]:1-[C;H0;D3;+0:9](=[O;D1;H0:10])-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15] | null | [] | null | null | 2 | HOUR | To a solution of 5-methyl-furan-2,4-dicarboxylic acid-2-methyl ester (23) (100 mg) in N,N-dimethylformamide (3.0 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (228 mg), diisopropylethylamine (0.56 mL) and 4′-methoxy-biphenyl-4-ylamine (120 mg). The resulting solution was stir... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Primary amine | Carboxylic acid.Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccoc1 | HO- | CN(C=O)C.C(C)(=O)OCC | null | 2 | COC(=O)c1cc(C(=O)O)c(C)o1.COc1ccc(-c2ccc(N)cc2)cc1>CN(C=O)C.C(C)(=O)OCC>COc1ccc(-c2ccc(NC(=O)c3cc(C(=O)O)oc3C)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-01f9e44084024917a8d3449096b9c05f | COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1>>Cc1oc(C(=O)O)cc1COc1ccc(I)cc1 | COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)I)C.[OH-].[Li+].Cl>>IC1=CC=C(OCC=2C=C(OC2C)C(=O)O)C=C1 | C[O:7][C:5]([c:4]1[o:3][c:2]([CH3:1])[c:9]([CH2:10][O:11][c:12]2[cH:13][cH:14][c:15]([I:16])[cH:17][cH:18]2)[cH:8]1)=[O:6]>>[CH3:1][c:2]1[o:3][c:4]([C:5](=[O:6])[OH:7])[cH:8][c:9]1[CH2:10][O:11][c:12]1[cH:13][cH:14][c:15]([I:16])[cH:17][cH:18]1 | COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1 | Cc1oc(C(=O)O)cc1COc1ccc(I)cc1 | null | null | O1CCCC1.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(OCc2ccoc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#8;a:5]>>[#8;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 70.4 | [{"value": 70.4, "product": "IC1=CC=C(OCC=2C=C(OC2C)C(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred solution of 4-(4-iodo-phenoxymethyl)-5-methyl-furan-2-carboxylic acid methyl ester (20) (2.7 g) in tetrahydrofuran (25 mL) was treated with a solution of lithium hydroxide (1.5 g) in water (2 mL). After 3 hours the reaction mixture was diluted with water and acidified to pH 2 with 1.0 M hydrochloric acid. The... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccoc1.c1ccccc1 | Other | O1CCCC1.O | null | null | COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1>O1CCCC1.O>Cc1oc(C(=O)O)cc1COc1ccc(I)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b39b01417a2b446bb848c76274443639 | CCOC(=O)CBr.Cc1occc1CO[Si](C(C)C)(C(C)C)C(C)C>>CCOC(=O)Cc1cc(CO[Si](C(C)C)(C(C)C)C(C)C)c(C)o1 | BrCC(=O)OCC.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)(C)[Si](OCC1=C(OC=C1)C)(C(C)C)C(C)C.C(CCC)[Li].[Cl-].O1C(=CC=C1)[Zn+]>>C(C)OC(CC=1OC(=C(C1)CO[Si](C(C)C)(C(C)C)C(C)C)C)=O | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[cH:7]1[cH:8][c:9]([CH2:10][O:11][Si:12]([CH:13]([CH3:14])[CH3:15])([CH:16]([CH3:17])[CH3:18])[CH:19]([CH3:20])[CH3:21])[c:22]([CH3:23])[o:24]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][c:9]([CH2:10][O:11][Si:12]([CH:13]([CH3:14])[CH3:15])([CH:16]([CH3:17])[CH3:18])[... | CCOC(=O)CBr.Cc1occc1CO[Si](C(C)C)(C(C)C)C(C)C | CCOC(=O)Cc1cc(CO[Si](C(C)C)(C(C)C)C(C)C)c(C)o1 | null | C/C(=C/C(=O)C)/[O-].C/C(=C/C(=O)C)/[O-].[Ni+2].[Cl-].[Zn+2].[Cl-] | O1CCCC1 | C-C Coupling | Friedel-Crafts alkylation with halide | 93fdde097896472bfc12eb49e0fb34940611c3ffece494af1ba9bc1fd805c2ea | 0061a06af9fc64155952582b91b574e4abd8908ca14244f15179c2400b24dd08 | c1ccoc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[#8;a:6]1:[c:7]:[c:8]:[c:9]:[cH;D2;+0:10]:1>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[c;H0;D3;+0:10]1:[#8;a:6]:[c:7]:[c:8]:[c:9]:1 | null | [] | 0 | CELSIUS | 30 | MINUTE | A solution of triisopropyl-(2-methyl-furan-3-ylmethoxy)-silane (14) (5.0 g) in tetrahydrofuran (15 mL) was cooled to −78° C. with stirring. This solution was treated drop-wise with n-butyl lithium (2.5 M in hexanes, 8.94 mL). The resulting solution was warmed to 0° C. and allowed to stand for 30 minutes after which a s... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | c1ccoc1 | c1ccoc1 | c1ccoc1 | HBr | C/C(=C/C(=O)C)/[O-].C/C(=C/C(=O)C)/[O-].[Ni+2].[Cl-].[Zn+2].[Cl-].O1CCCC1 | 0 | 0.5 | CCOC(=O)CBr.Cc1occc1CO[Si](C(C)C)(C(C)C)C(C)C>C/C(=C/C(=O)C)/[O-].C/C(=C/C(=O)C)/[O-].[Ni+2].[Cl-].[Zn+2].[Cl-].O1CCCC1>CCOC(=O)Cc1cc(CO[Si](C(C)C)(C(C)C)C(C)C)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8d40e02461f94836b554b430ff35d267 | CCOC(=O)Cc1cc(CO[Si](C(C)C)(C(C)C)C(C)C)c(C)o1>>CCOC(=O)Cc1cc(CO)c(C)o1 | C(C)OC(CC=1OC(=C(C1)CO[Si](C(C)C)(C(C)C)C(C)C)C)=O.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>C(C)OC(CC=1OC(=C(C1)CO)C)=O | CC(C)[Si](C(C)C)(C(C)C)[O:11][CH2:10][c:9]1[cH:8][c:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[o:14][c:12]1[CH3:13]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][c:9]([CH2:10][OH:11])[c:12]([CH3:13])[o:14]1 | CCOC(=O)Cc1cc(CO[Si](C(C)C)(C(C)C)C(C)C)c(C)o1 | CCOC(=O)Cc1cc(CO)c(C)o1 | null | null | O1CCCC1 | Deprotection | Alcohol deprotection from silyl ethers | 488547c1043a845c08188be7baa01e2ee1f8d7661927552d481c2d214b18b6c0 | 5c02ee98cb6b210a313993bea9e102110eb73637a50746f5457590f98613069b | c1ccoc1 | C-C(-C)-[Si](-[O;H0;D2;+0:1]-[C:2]-[c:3]:[c:4]:[#8;a:5])(-C(-C)-C)-C(-C)-C>>[#8;a:5]:[c:4]:[c:3]-[C:2]-[OH;D1;+0:1] | 67.3 | [{"value": 67.3, "product": "C(C)OC(CC=1OC(=C(C1)CO)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of (5-methyl-4-triisopropylsilanyloxymethyl-furan-2-yl)-acetic acid ethyl ester (29) (0.5 g) in tetrahydrofuran (3.0 mL) was cooled to 0° C. with stirring and treated with tetrabutylammonium fluoride (1.0 M solution in tetrahydrofuran, 2.82 mL) under argon. After 30 minutes, the resulting solution was concen... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Primary alcohol | null | null | c1ccoc1 | Other | O1CCCC1 | null | 0.5 | CCOC(=O)Cc1cc(CO[Si](C(C)C)(C(C)C)C(C)C)c(C)o1>O1CCCC1>CCOC(=O)Cc1cc(CO)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e39fb497513b41a8a2dc3023a8229f53 | Cc1occc1CO[Si](C(C)C)(C(C)C)C(C)C>>Cc1oc(C=O)cc1CO[Si](C(C)C)(C(C)C)C(C)C | C(C)(C)[Si](OCC1=C(OC=C1)C)(C(C)C)C(C)C.O1CCCC1.C(C)(CC)[Li].[Cl-].[NH4+]>>CC1=C(C=C(O1)C=O)CO[Si](C(C)C)(C(C)C)C(C)C | [CH3:1][c:2]1[o:3][cH:4][cH:7][c:8]1[CH2:9][O:10][Si:11]([CH:12]([CH3:13])[CH3:14])([CH:15]([CH3:16])[CH3:17])[CH:18]([CH3:19])[CH3:20]>>[CH3:1][c:2]1[o:3][c:4]([CH:5]=[O:6])[cH:7][c:8]1[CH2:9][O:10][Si:11]([CH:12]([CH3:13])[CH3:14])([CH:15]([CH3:16])[CH3:17])[CH:18]([CH3:19])[CH3:20] | Cc1occc1CO[Si](C(C)C)(C(C)C)C(C)C | Cc1oc(C=O)cc1CO[Si](C(C)C)(C(C)C)C(C)C | null | null | null | Miscellaneous | OtherReaction | cae1cf39610b30a86caac44da7f4804528832aa7a233d782930e12364457f524 | 3cccf922e74135722ee21a46ad7578302a8603e1f71d6f2113cd42de4ba0cf73 | c1ccoc1 | [#8;a:1]1:[c:2]:[c:3]:[c:4]:[cH;D2;+0:5]:1>>[O;D1;H0:6]=[C:7]-[c;H0;D3;+0:5]1:[#8;a:1]:[c:2]:[c:3]:[c:4]:1 | null | [] | null | null | null | null | A solution of triisopropyl-(2-methyl-furan-3-ylmethoxy)-silane (14) (10 g) in tetrahydrofuran (250 mL) was cooled to −78° C. with stirring, and then sec-butyllithium (1.3 M in cyclohexane; 37.25 mL) was added drop-wise over 10 mins. After stirring for 45 mins at −78° C., the cooling bath was removed for a period of 15 ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aldehyde | c1ccoc1 | c1ccoc1 | c1ccoc1 | Other | null | null | null | Cc1occc1CO[Si](C(C)C)(C(C)C)C(C)C>>Cc1oc(C=O)cc1CO[Si](C(C)C)(C(C)C)C(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-31f961aec1ce4f748b4be3af38423464 | CCOC(=O)C=Cc1cc(CO[Si](C(C)C)(C(C)C)C(C)C)c(C)o1>>CCOC(=O)CCc1cc(CO[Si](C(C)C)(C(C)C)C(C)C)c(C)o1 | C(C)OC(C=CC=1OC(=C(C1)CO[Si](C(C)C)(C(C)C)C(C)C)C)=O>>C(C)OC(CCC=1OC(=C(C1)CO[Si](C(C)C)(C(C)C)C(C)C)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH:7][c:8]1[cH:9][c:10]([CH2:11][O:12][Si:13]([CH:14]([CH3:15])[CH3:16])([CH:17]([CH3:18])[CH3:19])[CH:20]([CH3:21])[CH3:22])[c:23]([CH3:24])[o:25]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][c:8]1[cH:9][c:10]([CH2:11][O:12][Si:13]([CH:14]([CH3:15])[CH3:16])([CH:17]([CH3:18]... | CCOC(=O)C=Cc1cc(CO[Si](C(C)C)(C(C)C)C(C)C)c(C)o1 | CCOC(=O)CCc1cc(CO[Si](C(C)C)(C(C)C)C(C)C)c(C)o1 | null | [Pd] | C(C)(=O)OCC | Reduction | Hydrogenation (double to single) | c04c38f95d7b746e5bdb99c368a7a33956c97b95b54c7ad89be2a85526386ec9 | 9a50abf8d2e4cd9195d7a0cadbe97483a261a81cf70b653cfddd5ecf76d383a6 | c1ccoc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D2;+0:5]=[CH;D2;+0:6]-[c:7](:[c:8]):[#8;a:9]:[c:10]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[c:7](:[c:8]):[#8;a:9]:[c:10] | 104.4 | [{"value": 104.4, "product": "C(C)OC(CCC=1OC(=C(C1)CO[Si](C(C)C)(C(C)C)C(C)C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-(5-methyl-4-triisopropylsilanyloxymethyl-furan-2-yl)-acrylic acid ethyl ester (34) (1.0 g) in ethyl acetate (70 mL) was treated with 5% w/w palladium on carbon (350 mg) and hydrogenated at 1 atmosphere for exactly 1¼ hours at room temperature. The reaction mixture was filtered through filter-aid and the... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | c1ccoc1 | null | [Pd].C(C)(=O)OCC | null | null | CCOC(=O)C=Cc1cc(CO[Si](C(C)C)(C(C)C)C(C)C)c(C)o1>[Pd].C(C)(=O)OCC>CCOC(=O)CCc1cc(CO[Si](C(C)C)(C(C)C)C(C)C)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4701f04e25814d9fb2341f2dae6ce08f | CCOC(=O)CCc1cc(CO)c(C)o1.Oc1ccc(-c2ccccc2)cc1>>Cc1oc(CCC(=O)O)cc1COc1ccc(-c2ccccc2)cc1 | C(C)OC(CCC=1OC(=C(C1)CO)C)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=C(C=C1)O)C1=CC=CC=C1.CC(C)OC(=O)/N=N/C(=O)OC(C)C>>C1(=CC=C(C=C1)OCC=1C=C(OC1C)CCC(=O)O)C1=CC=CC=C1 | CC[O:9][C:7]([CH2:6][CH2:5][c:4]1[o:3][c:2]([CH3:1])[c:11]([CH2:12][OH:13])[cH:10]1)=[O:8].O[c:14]1[cH:15][cH:16][c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[cH:24][cH:25]1>>[CH3:1][c:2]1[o:3][c:4]([CH2:5][CH2:6][C:7](=[O:8])[OH:9])[cH:10][c:11]1[CH2:12][O:13][c:14]1[cH:15][cH:16][c:17](-[c:18]2[cH:19][cH:20][c... | CCOC(=O)CCc1cc(CO)c(C)o1.Oc1ccc(-c2ccccc2)cc1 | Cc1oc(CCC(=O)O)cc1COc1ccc(-c2ccccc2)cc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 387928e2999368eba02196099cabcd9fef681a6c27addbdc8240d657651def8d | 9653d63179b641796999681486e0249947865421087fe94dd6954f3668089e9b | c1ccc(-c2ccc(OCc3ccoc3)cc2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[#8;a:5]:[c:6]:[c:7]-[C:8]-[OH;D1;+0:9].O-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[#8;a:5]:[c:6]:[c:7]-[C:8]-[O;H0;D2;+0:9]-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14].[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 3.9 | [{"value": 3.9, "product": "C1(=CC=C(C=C1)OCC=1C=C(OC1C)CCC(=O)O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 10 | MINUTE | To a stirred, cooled 0° C. solution, in tetrahydrofuran (2.5 mL), a solution of 3-(4-hydroxymethyl-5-methyl-furan-2-yl)-propionic acid ethyl ester (36) (400 mg) in tetrahydrofuran (2.5 mL) was cooled to 0° C. and treated successively with triphenylphosphine (542 mg), biphenyl-4-ol (353 mg) and diisopropylazodicarboxyla... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary alcohol.Aromatic alcohol | Carboxylic acid.Ether | c1ccccc1 | c1ccccc1 | c1ccoc1.c1ccccc1.c1ccccc1 | HO- | O1CCCC1 | 0 | 0.166667 | CCOC(=O)CCc1cc(CO)c(C)o1.Oc1ccc(-c2ccccc2)cc1>O1CCCC1>Cc1oc(CCC(=O)O)cc1COc1ccc(-c2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6c2940245aaf4bbfa62e61b4eb37787a | Cc1occc1CO.Oc1ccc(-c2ccccc2)cc1>>Cc1occc1COc1ccc(-c2ccccc2)cc1 | CC(C)OC(=O)/N=N/C(=O)OC(C)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=C(C=C1)O)C1=CC=CC=C1.CC=1OC=CC1CO>>C1(=CC=C(C=C1)OCC1=C(OC=C1)C)C1=CC=CC=C1 | [CH3:1][c:2]1[o:3][cH:4][cH:5][c:6]1[CH2:7][OH:8].O[c:9]1[cH:10][cH:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1>>[CH3:1][c:2]1[o:3][cH:4][cH:5][c:6]1[CH2:7][O:8][c:9]1[cH:10][cH:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1 | Cc1occc1CO.Oc1ccc(-c2ccccc2)cc1 | Cc1occc1COc1ccc(-c2ccccc2)cc1 | null | null | C(C)OCC | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 8915084acbaaf997bf0f89ff5187cb2f89c25dc683fffc57b3391298c8430dd9 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(-c2ccc(OCc3ccoc3)cc2)cc1 | O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8;a:6]:[c:7]:[c:8]-[C:9]-[OH;D1;+0:10]>>[#8;a:6]:[c:7]:[c:8]-[C:9]-[O;H0;D2;+0:10]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 59.4 | [{"value": 59.4, "product": "C1(=CC=C(C=C1)OCC1=C(OC=C1)C)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of (2-methyl-furan-3-yl)-methanol (1) (5.0 g) in diethyl ether (75 mL) was cooled to 0° C. with stirring and treated with triphenylphosphine (12.85 g) and biphenyl-4-ol (7.59 g). The resulting solution was then treated drop-wise with diisopropylazodicarboxylate (9.75 mL). After stirring for 10 minutes at 0° ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccoc1.c1ccccc1.c1ccccc1 | HO- | C(C)OCC | null | null | Cc1occc1CO.Oc1ccc(-c2ccccc2)cc1>C(C)OCC>Cc1occc1COc1ccc(-c2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-19f2272b9fd148bc8448f74140c8d61c | Cc1oc(S(N)(=O)=O)cc1COc1ccc(-c2ccccc2)cc1.O=C(O)c1ccccc1>>Cc1oc(S(=O)(=O)NC(=O)c2ccccc2)cc1COc1ccc(-c2ccccc2)cc1 | Cl.CN(CCCN=C=NCC)C.C1(=CC=C(C=C1)OCC=1C=C(OC1C)S(=O)(=O)N)C1=CC=CC=C1.C(C1=CC=CC=C1)(=O)O>>C(C1=CC=CC=C1)(=O)NS(=O)(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)C1=CC=CC=C1)C | [CH3:1][c:2]1[o:3][c:4]([S:5](=[O:6])(=[O:7])[NH2:8])[cH:17][c:18]1[CH2:19][O:20][c:21]1[cH:22][cH:23][c:24](-[c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)[cH:31][cH:32]1.O[C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][c:2]1[o:3][c:4]([S:5](=[O:6])(=[O:7])[NH:8][C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:... | Cc1oc(S(N)(=O)=O)cc1COc1ccc(-c2ccccc2)cc1.O=C(O)c1ccccc1 | Cc1oc(S(=O)(=O)NC(=O)c2ccccc2)cc1COc1ccc(-c2ccccc2)cc1 | null | CN(C)C1=CC=NC=C1 | O1CCCC1.CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 195a412a8235704efe2985cdc18467ba661e632bab7b61944399ecc813e32a09 | 5e4665bad9c6f58dddd98c5f95e436c640b4c0118b04efea5cd58c7d1755401d | O=C(NS(=O)(=O)c1cc(COc2ccc(-c3ccccc3)cc2)co1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#8;a:6]:[c:7]-[#16:8](-[NH2;D1;+0:9])(=[O;D1;H0:10])=[O;D1;H0:11]>>[#8;a:6]:[c:7]-[#16:8](=[O;D1;H0:10])(=[O;D1;H0:11])-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | To a stirred solution of benzoic acid (61 mg) in a mixture of tetrahydrofuran (10 mL) and N,N-dimethylformamide (5 mL) was added 4-(N,N-dimethylamino)pyridine (3.0 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (118 mg) and 4-(biphenyl-4-yloxymethyl)-5-methyl-furan-2-sulfonic acid amide (45) (206 mg).... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Carboxylic acid | Sulfonamide.Secondary amide | null | null | c1ccoc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | CN(C)C1=CC=NC=C1.O1CCCC1.CN(C=O)C | null | null | Cc1oc(S(N)(=O)=O)cc1COc1ccc(-c2ccccc2)cc1.O=C(O)c1ccccc1>CN(C)C1=CC=NC=C1.O1CCCC1.CN(C=O)C>Cc1oc(S(=O)(=O)NC(=O)c2ccccc2)cc1COc1ccc(-c2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-02dc82f64f374c8c91b15f796bec0e0c | CCCC(=O)Cl.Cc1oc(S(N)(=O)=O)cc1COc1ccc(-c2ccccc2)cc1>>CCCC(=O)NS(=O)(=O)c1cc(COc2ccc(-c3ccccc3)cc2)c(C)o1 | C1(=CC=C(C=C1)OCC=1C=C(OC1C)S(=O)(=O)N)C1=CC=CC=C1.C(C)N(CC)CC.C(CCC)(=O)Cl>>C(CCC)(=O)NS(=O)(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)C1=CC=CC=C1)C | Cl[C:4]([CH2:3][CH2:2][CH3:1])=[O:5].[NH2:6][S:7](=[O:8])(=[O:9])[c:10]1[cH:11][c:12]([CH2:13][O:14][c:15]2[cH:16][cH:17][c:18](-[c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[cH:25][cH:26]2)[c:27]([CH3:28])[o:29]1>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[NH:6][S:7](=[O:8])(=[O:9])[c:10]1[cH:11][c:12]([CH2:13][O:14][c:15]2[cH... | CCCC(=O)Cl.Cc1oc(S(N)(=O)=O)cc1COc1ccc(-c2ccccc2)cc1 | CCCC(=O)NS(=O)(=O)c1cc(COc2ccc(-c3ccccc3)cc2)c(C)o1 | null | CN(C1=CC=NC=C1)C | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 403eb34e708e50f7077a9da490b1654c837258ce901614ddd1204eb6f2a10a27 | 37dfa12f19cd8cec29206fb8a18b7504935d92bc326a2084e9ef8a13076d3b87 | c1ccc(-c2ccc(OCc3ccoc3)cc2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#8;a:5]:[c:6]-[#16:7](-[NH2;D1;+0:8])(=[O;D1;H0:9])=[O;D1;H0:10]>>[#8;a:5]:[c:6]-[#16:7](=[O;D1;H0:9])(=[O;D1;H0:10])-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | 79.5 | [{"value": 79.5, "product": "C(CCC)(=O)NS(=O)(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)C1=CC=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a stirred solution of 4-(biphenyl-4-yloxymethyl)-5-methyl-furan-2-sulphonic acid amide (45) (50 mg, 0.146 mmoles) in dichloromethane (5.0 ml) was added triethylamine (26 μl, 0.189 mmoles), dimethyl-pyridin-4-yl-amine (1 mg) and butyryl chloride (19 μl, 0.184 mmoles). After stirring for 16 hours at room temperature t... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Sulfonamide | Sulfonamide.Secondary amide | null | null | c1ccoc1.c1ccccc1.c1ccccc1 | HCl | CN(C1=CC=NC=C1)C.ClCCl | null | 16 | CCCC(=O)Cl.Cc1oc(S(N)(=O)=O)cc1COc1ccc(-c2ccccc2)cc1>CN(C1=CC=NC=C1)C.ClCCl>CCCC(=O)NS(=O)(=O)c1cc(COc2ccc(-c3ccccc3)cc2)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7deec222c1444263b279988f5b822d56 | CC1(C)OB(c2ccc(O)cc2)OC1(C)C.COC(=O)c1cc(CO)c(C)o1>>COC(=O)c1cc(COc2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c(C)o1 | COC(=O)C=1OC(=C(C1)CO)C.CC1(OB(OC1(C)C)C1=CC=C(C=C1)O)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)B1OC(C(O1)(C)C)(C)C)C | [OH:9][c:10]1[cH:11][cH:12][c:13]([B:14]2[O:15][C:16]([CH3:17])([CH3:18])[C:19]([CH3:20])([CH3:21])[O:22]2)[cH:23][cH:24]1.O[CH2:8][c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[o:27][c:25]1[CH3:26]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][O:9][c:10]2[cH:11][cH:12][c:13]([B:14]3[O:15][C:16]([CH3:17])([CH3:18])... | CC1(C)OB(c2ccc(O)cc2)OC1(C)C.COC(=O)c1cc(CO)c(C)o1 | COC(=O)c1cc(COc2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c(C)o1 | null | null | null | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1cc(COc2ccc(B3OCCO3)cc2)co1 | O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4](-[C:5](-[#8:6])=[O;D1;H0:7]):[#8;a:8]:[c:9]:1-[C;D1;H3:10].[OH;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]1:[#8;a:8]:[c:9](-[C;D1;H3:10]):[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:3]:1 | null | [] | 0 | CELSIUS | 72 | HOUR | A mixture of 4-hydroxymethyl-5-methyl-furan-2-carboxylic acid methyl ester (16) (0.5 g), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (1.9 g) and triphenylphosphine (2.3 g) in dry tetrahydrofuan (20 mL) under a nitrogen atmosphere was cooled to 0° C. Di-isopropylazodicarboxylate (1.8 mL) was added drop-wise ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccoc1.c1ccccc1.[B]1OCCO1 | HO- | null | 0 | 72 | CC1(C)OB(c2ccc(O)cc2)OC1(C)C.COC(=O)c1cc(CO)c(C)o1>>COC(=O)c1cc(COc2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8fd90a8774c149268ada582b7a92c9ed | COC(=O)c1cc(COc2ccc(-c3ccc(OC)cn3)cc2)c(C)o1>>COc1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)nc1 | COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)C1=NC=C(C=C1)OC)C>>COC=1C=CC(=NC1)C1=CC=C(OCC=2C=C(OC2C)C(=O)O)C=C1 | C[O:18][C:16]([c:15]1[cH:14][c:13]([CH2:12][O:11][c:10]2[cH:9][cH:8][c:7](-[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:25][n:24]3)[cH:23][cH:22]2)[c:20]([CH3:21])[o:19]1)=[O:17]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([O:11][CH2:12][c:13]3[cH:14][c:15]([C:16](=[O:17])[OH:18])[o:19][c:20]3[CH3:21])[c... | COC(=O)c1cc(COc2ccc(-c3ccc(OC)cn3)cc2)c(C)o1 | COc1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)nc1 | null | null | O1CCCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ccc(OCc3ccoc3)cc2)nc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#8;a:5]>>[#8;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 53.6 | [{"value": 53.6, "product": "COC=1C=CC(=NC1)C1=CC=C(OCC=2C=C(OC2C)C(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 4-[4-(5-methoxy-pyridin-2-yl)-phenoxymethyl]-5-methyl-furan-2-carboxylic acid methyl ester (52) (118 mg, 0.33 mmoles) in dry tetrahydrofuran (10 ml) was treated with potassium trimethylsilanoate (260 mg, 2.0 mmoles) and the mixture stirred under an argon atmosphere for 2 hours. After evaporation of the so... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1.c1ccccc1.c1ccoc1 | Other | O1CCCC1 | null | 2 | COC(=O)c1cc(COc2ccc(-c3ccc(OC)cn3)cc2)c(C)o1>O1CCCC1>COc1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)nc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fe66121b7403479f809e32a3e651e0d7 | COC(=O)c1cc(COc2ccc(-c3ccc(OC)cn3)cc2)c(C)o1>>COc1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)nc1 | COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)C1=NC=C(C=C1)OC)C.[OH-].[Li+]>>COC=1C=CC(=NC1)C1=CC=C(OCC=2C=C(OC2C)C(=O)O)C=C1 | C[O:18][C:16]([c:15]1[cH:14][c:13]([CH2:12][O:11][c:10]2[cH:9][cH:8][c:7](-[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:25][n:24]3)[cH:23][cH:22]2)[c:20]([CH3:21])[o:19]1)=[O:17]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([O:11][CH2:12][c:13]3[cH:14][c:15]([C:16](=[O:17])[OH:18])[o:19][c:20]3[CH3:21])[c... | COC(=O)c1cc(COc2ccc(-c3ccc(OC)cn3)cc2)c(C)o1 | COc1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)nc1 | null | null | O1CCCC1.CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ccc(OCc3ccoc3)cc2)nc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#8;a:5]>>[#8;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | 16 | HOUR | A mixture of 4-[4-(5-methoxy-pyridin-2-yl)-phenoxymethyl]-5-methyl-furan-2-carboxylic acid methyl ester (52) (70 mg) and 1M aqueous lithium hydroxide (1 mL) in tetrahydrofuran/methanol (2:1 by volume) (12 mL) was stirred at room temperature for 16 hours. The reaction mixture was acidified to between pH6 and pH7, and pa... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1.c1ccccc1.c1ccoc1 | Other | O1CCCC1.CO | null | 16 | COC(=O)c1cc(COc2ccc(-c3ccc(OC)cn3)cc2)c(C)o1>O1CCCC1.CO>COc1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)nc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-56a99a1d74b947438319981ba013fc7b | COC(=O)c1cc(CO)c(C)o1.Oc1ccc(I)nc1>>COC(=O)c1cc(COc2ccc(I)nc2)c(C)o1 | COC(=O)C=1OC(=C(C1)CO)C.IC1=NC=C(C=C1)O>>COC(=O)C=1OC(=C(C1)COC=1C=NC(=CC1)I)C | O[CH2:8][c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[o:19][c:17]1[CH3:18].[OH:9][c:10]1[cH:11][cH:12][c:13]([I:14])[n:15][cH:16]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][O:9][c:10]2[cH:11][cH:12][c:13]([I:14])[n:15][cH:16]2)[c:17]([CH3:18])[o:19]1 | COC(=O)c1cc(CO)c(C)o1.Oc1ccc(I)nc1 | COC(=O)c1cc(COc2ccc(I)nc2)c(C)o1 | null | null | null | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1cncc(OCc2ccoc2)c1 | O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4](-[C:5](-[#8:6])=[O;D1;H0:7]):[#8;a:8]:[c:9]:1-[C;D1;H3:10].[OH;D1;+0:11]-[c:12](:[c:13]):[c:14]:[#7;a:15]:[c:16]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]1:[#8;a:8]:[c:9](-[C;D1;H3:10]):[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:11]-[c:12](:[c:13]):[c:14]:[#7;a:15]:[c:16]):[c:3]:1 | null | [] | null | null | null | null | Compound (54) was prepared from compound (16) and 2-iodo-5-hydroxy-pyridine in a manner analagous to that described in Example 5(a). LC/MS System A: Rt=3.52 mins, m/z=374 ((M+H) for C13H12INO4)
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccoc1.c1ccncc1 | HO- | null | null | null | COC(=O)c1cc(CO)c(C)o1.Oc1ccc(I)nc1>>COC(=O)c1cc(COc2ccc(I)nc2)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6dee0ec125d049e8b6c4550813e014e9 | N.O=S(=O)(Cl)CCCN1CCOCC1>>NS(=O)(=O)CCCN1CCOCC1 | N.C(=O)=O.CC(=O)C.N1(CCOCC1)CCCS(=O)(=O)Cl>>N1(CCOCC1)CCCS(=O)(=O)N | [NH3:1].Cl[S:2](=[O:3])(=[O:4])[CH2:5][CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1>>[NH2:1][S:2](=[O:3])(=[O:4])[CH2:5][CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1 | N.O=S(=O)(Cl)CCCN1CCOCC1 | NS(=O)(=O)CCCN1CCOCC1 | null | null | ClCCl | Acylation | OtherReaction | 672a14b4f1ef0b966898e1b4c118f241f21df1d6e087372155b9d0c840dac61f | 29e1633db8f1f00444181a0bcac91d574ed806fddf9165be4c8478fc32a80994 | C1COCCN1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C:5].[NH3;D0;+0:6]>>[C:5]-[C:4]-[S;H0;D4;+0:1](-[NH2;D1;+0:6])(=[O;D1;H0:2])=[O;D1;H0:3] | null | [] | null | null | 24 | HOUR | Dichloromethane (40 ml) was saturated with ammonia gas with cooling (dry ice/acetone), and then 3-morpholin-4-yl-propane-1-sulphonyl chloride (279 mg, 1.23 mmoles) was added. The mixture was stirred at room temperature for 24 hours. The mixture was filtered, the filtrate evaporated and the residue was dried at 40° C. i... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Sulfonamide | null | null | C1COCC[NH]1 | HCl | ClCCl | null | 24 | N.O=S(=O)(Cl)CCCN1CCOCC1>ClCCl>NS(=O)(=O)CCCN1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7ad047b539f64ba7879af67e63b2cabb | COc1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)cc1.NS(=O)(=O)CCCN1CCOCC1>>COc1ccc(-c2ccc(OCc3cc(C(=O)NS(=O)(=O)CCCN4CCOCC4)oc3C)cc2)cc1 | COC1=CC=C(C=C1)C1=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)O.N1(CCOCC1)CCCS(=O)(=O)N>>COC1=CC=C(C=C1)C1=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)NS(=O)(=O)CCCN1CCOCC1 | O[C:16]([c:15]1[cH:14][c:13]([CH2:12][O:11][c:10]2[cH:9][cH:8][c:7](-[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:37][cH:36]3)[cH:35][cH:34]2)[c:32]([CH3:33])[o:31]1)=[O:17].[NH2:18][S:19](=[O:20])(=[O:21])[CH2:22][CH2:23][CH2:24][N:25]1[CH2:26][CH2:27][O:28][CH2:29][CH2:30]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH... | COc1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)cc1.NS(=O)(=O)CCCN1CCOCC1 | COc1ccc(-c2ccc(OCc3cc(C(=O)NS(=O)(=O)CCCN4CCOCC4)oc3C)cc2)cc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 195a412a8235704efe2985cdc18467ba661e632bab7b61944399ecc813e32a09 | 5e4665bad9c6f58dddd98c5f95e436c640b4c0118b04efea5cd58c7d1755401d | O=C(NS(=O)(=O)CCCN1CCOCC1)c1cc(COc2ccc(-c3ccccc3)cc2)co1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[C:7]-[#16:8](-[NH2;D1;+0:9])(=[O;D1;H0:10])=[O;D1;H0:11]>>[C:7]-[#16:8](=[O;D1;H0:10])(=[O;D1;H0:11])-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6] | null | [] | null | null | null | null | Compound (59) was prepared from compounds (4) and (58) by adapting the procedure of Example 2A. LC/MS System D; Rt=4.97 mins, m/z (ES+)=529 (M+H for C27H32N2O7S).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Carboxylic acid | Sulfonamide.Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccoc1.C1COCC[NH]1 | HO- | null | null | null | COc1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)cc1.NS(=O)(=O)CCCN1CCOCC1>>COc1ccc(-c2ccc(OCc3cc(C(=O)NS(=O)(=O)CCCN4CCOCC4)oc3C)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-560f3b6afd6544568b40a77d5eba2f20 | Cc1ccccc1S(N)(=O)=O.Cc1oc(C(=O)O)cc1COc1ccc(-c2ccccc2)cc1>>Cc1ccccc1S(=O)(=O)NC(=O)c1cc(COc2ccc(-c3ccccc3)cc2)c(C)o1 | C1(=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)O)C1=CC=CC=C1.CC1=C(C=CC=C1)S(=O)(=O)N.Cl.CN(CCCN=C=NCC)C>>C1(=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)NS(=O)(=O)C1=C(C=CC=C1)C)C1=CC=CC=C1 | [CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[S:8](=[O:9])(=[O:10])[NH2:11].O[C:12](=[O:13])[c:14]1[cH:15][c:16]([CH2:17][O:18][c:19]2[cH:20][cH:21][c:22](-[c:23]3[cH:24][cH:25][cH:26][cH:27][cH:28]3)[cH:29][cH:30]2)[c:31]([CH3:32])[o:33]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[S:8](=[O:9])(=[O:10])[NH:11][C:12](=[... | Cc1ccccc1S(N)(=O)=O.Cc1oc(C(=O)O)cc1COc1ccc(-c2ccccc2)cc1 | Cc1ccccc1S(=O)(=O)NC(=O)c1cc(COc2ccc(-c3ccccc3)cc2)c(C)o1 | null | CN(C)C1=CC=NC=C1 | O1CCCC1.C(C)#N | Acylation | Carboxylic acid with primary amine to amide | 195a412a8235704efe2985cdc18467ba661e632bab7b61944399ecc813e32a09 | 5e4665bad9c6f58dddd98c5f95e436c640b4c0118b04efea5cd58c7d1755401d | O=C(NS(=O)(=O)c1ccccc1)c1cc(COc2ccc(-c3ccccc3)cc2)co1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[NH2;D1;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11]>>[O;D1;H0:9]=[#16:8](=[O;D1;H0:10])(-[c:11])-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6] | 26.7 | [{"value": 26.7, "product": "C1(=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)NS(=O)(=O)C1=C(C=CC=C1)C)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A stirred solution of 4-(biphenyl-4-yloxymethyl)-5-methyl-furan-2-carboxylic acid (18) (50 mg, 0.162 mmoles), 2-methyl-benzenesulphonamide (42 mg, 0.243 mmoles) and 4-(N,N-dimethylamino)-pyridine (2.5 mg) in a mixture of tetrahydrofuran (8 ml) and acetonitrile (2 ml) was treated with 1-(3-dimethylaminopropyl)-3-ethylca... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Carboxylic acid | Sulfonamide.Secondary amide | null | null | c1ccccc1.c1ccoc1.c1ccccc1.c1ccccc1 | HO- | CN(C)C1=CC=NC=C1.O1CCCC1.C(C)#N | null | 16 | Cc1ccccc1S(N)(=O)=O.Cc1oc(C(=O)O)cc1COc1ccc(-c2ccccc2)cc1>CN(C)C1=CC=NC=C1.O1CCCC1.C(C)#N>Cc1ccccc1S(=O)(=O)NC(=O)c1cc(COc2ccc(-c3ccccc3)cc2)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8a2e8f2af4d64aa7aa985cdd5f35656f | CCOC(=O)Cc1ccoc1C>>Cc1occc1CCO | C(C)OC(CC1=C(OC=C1)C)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>CC=1OC=CC1CCO | CCO[C:8]([CH2:7][c:6]1[c:2]([CH3:1])[o:3][cH:4][cH:5]1)=[O:9]>>[CH3:1][c:2]1[o:3][cH:4][cH:5][c:6]1[CH2:7][CH2:8][OH:9] | CCOC(=O)Cc1ccoc1C | Cc1occc1CCO | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccoc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[c:4]:[c:5]:[#8;a:6]>>[#8;a:6]:[c:5]:[c:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | 0 | CELSIUS | 3 | HOUR | A solution of (2-methyl-furan-3-yl)-acetic acid ethyl ester (11.8 g, 70.2 mmoles) in tetrahydrofuran (50 ml) was added to a stirred suspension of lithium aluminium hydride (2.66 g, 70.2 mmoles) under a nitrogen atmosphere and with cooling to 0° C. When the addition was complete the mixture was stirred at room temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccoc1 | HO- | O1CCCC1 | 0 | 3 | CCOC(=O)Cc1ccoc1C>O1CCCC1>Cc1occc1CCO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d8ebeacd351047e682146583a90b1d2f | CCOC(=O)CC(=O)C(C)C>>CCOC(=O)c1ccoc1C(C)C | [OH-].[Na+].C(C)OC(CC(C(C)C)=O)=O.ClC(CCl)OCC>>C(C)OC(=O)C1=C(OC=C1)C(C)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:10](=[O:9])[CH:11]([CH3:12])[CH3:13]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][o:9][c:10]1[CH:11]([CH3:12])[CH3:13] | CCOC(=O)CC(=O)C(C)C | CCOC(=O)c1ccoc1C(C)C | null | null | O.C(C)OCC | Aromatic Heterocycle Formation | OtherReaction | 3d59eca64d9e08f3f2cf41a13f93be1239ae749d285b221a48e58749a8dba3ab | 0ee4fb987ebeea21a9d50ac911d0f83c8450e9a26ef48746d74554271dcaf444 | c1ccoc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[C:8](-[C;D1;H3:9])-[C;D1;H3:10]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:5]1:[c:11]:[c:12]:[o;H0;D2;+0:7]:[c;H0;D3;+0:6]:1-[C:8](-[C;D1;H3:9])-[C;D1;H3:10] | 69.5 | [{"value": 69.5, "product": "C(C)OC(=O)C1=C(OC=C1)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | An ice-chilled solution of sodium hydroxide (1.9 g) in water (25 ml) was added, during 40 minutes, to a stirred solution of 4-methyl-3-oxo-pentanoic acid ethyl ester (3 g, 18.96 mmoles) and 1,2-dichloro-1-ethoxy-ethane (3.3 g, 35.19 mmole) in diethyl ether (15 ml) with ice bath cooling. When the addition was complete t... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ester | null | c1ccoc1 | c1ccoc1 | Other | O.C(C)OCC | null | 1 | CCOC(=O)CC(=O)C(C)C>O.C(C)OCC>CCOC(=O)c1ccoc1C(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-96c7f09801eb4099a5dddb1b85969f7e | COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1.COc1ccc(B(O)O)cc1OC>>COc1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)cc1OC | COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)I)C.COC=1C=C(C=CC1OC)B(O)O.CN(C=O)C.C(C)(=O)[O-].[K+]>>COC=1C=C(C=CC1OC)C1=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)O | C[O:18][C:16]([c:15]1[cH:14][c:13]([CH2:12][O:11][c:10]2[cH:9][cH:8][c:7](I)[cH:23][cH:22]2)[c:20]([CH3:21])[o:19]1)=[O:17].OB(O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:25]([O:26][CH3:27])[cH:24]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([O:11][CH2:12][c:13]3[cH:14][c:15]([C:16](=[O:17])[OH:18])[o... | COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1.COc1ccc(B(O)O)cc1OC | COc1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)cc1OC | null | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2] | ClCCl.O | C-C Coupling | OtherReaction | 04157bef51d5543c035526858b11d2af2b78e75d38cd85edf56b617e6aebc946 | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2ccc(OCc3ccoc3)cc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#8;a:5].I-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10].O-B(-O)-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]>>[#8;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1].[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]):[c:9]:[c:10] | 60.8 | [{"value": 60.8, "product": "COC=1C=C(C=CC1OC)C1=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A stirred mixture of 4-(4-iodo-phenoxymethyl)-5-methyl-furan-2-carboxylic acid methyl ester (20) (0.025 g, 0.067 mmoles), (3,4-dimethoxyphenyl)-boronic acid (0.017 g, 0.093 mmoles), N,N-dimethylformamide (3 mL), potassium acetate (0.026 g) and [1,1′-bis(diphenylphosphino) ferrocene]dichloropalladium(II), complex with d... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccoc1 | HI.B | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].ClCCl.O | null | 24 | COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1.COc1ccc(B(O)O)cc1OC>C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].ClCCl.O>COc1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-52c36e7502654e76aab4d4a760d58f29 | COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1.OB(O)c1ccc2c(c1)OCO2>>Cc1oc(C(=O)O)cc1COc1ccc(-c2ccc3c(c2)OCO3)cc1 | COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)I)C.C1OC=2C=C(C=CC2O1)B(O)O>>O1COC2=C1C=CC(=C2)C2=CC=C(OCC=1C=C(OC1C)C(=O)O)C=C2 | C[O:7][C:5]([c:4]1[o:3][c:2]([CH3:1])[c:9]([CH2:10][O:11][c:12]2[cH:13][cH:14][c:15](I)[cH:25][cH:26]2)[cH:8]1)=[O:6].OB(O)[c:16]1[cH:17][cH:18][c:19]2[c:20]([cH:21]1)[O:22][CH2:23][O:24]2>>[CH3:1][c:2]1[o:3][c:4]([C:5](=[O:6])[OH:7])[cH:8][c:9]1[CH2:10][O:11][c:12]1[cH:13][cH:14][c:15](-[c:16]2[cH:17][cH:18][c:19]3[c:... | COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1.OB(O)c1ccc2c(c1)OCO2 | Cc1oc(C(=O)O)cc1COc1ccc(-c2ccc3c(c2)OCO3)cc1 | null | null | null | C-C Coupling | OtherReaction | 6edcd9e2b402dbd56bbc75a03f0214d18a4609f841b039e42a77bd180cb3ab1f | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1cc(COc2ccc(-c3ccc4c(c3)OCO4)cc2)co1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#8;a:5].I-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10].O-B(-O)-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]-[#8:16]>>[#8;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1].[#8:16]-[c:15]:[c:14]:[c;H0;D3;+0:11](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:12]:[c:13] | null | [] | null | null | null | null | Compound (28) was prepared from compound (20) and (3,4-methylenedioxyphenyl)-boronic acid by adapting the procedure of Example 24A. LC/MS System B; Rt=1.76 mins, m/z (ES−)=351 (M−H for C20H16O6).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1ccccc1.c1ccc2c(c1)OCO2 | c1ccccc1.c1ccc2c(c1)OCO2 | c1ccoc1.c1ccccc1.c1ccc2c(c1)OCO2 | HI.B | null | null | null | COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1.OB(O)c1ccc2c(c1)OCO2>>Cc1oc(C(=O)O)cc1COc1ccc(-c2ccc3c(c2)OCO3)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-529eedf26bf44583bbaeb734051aec2e | CCOc1ccc(B(O)O)cc1.COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1>>CCOc1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)cc1 | COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)I)C.C(C)OC1=CC=C(C=C1)B(O)O>>C(C)OC1=CC=C(C=C1)C1=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)O | OB(O)[c:7]1[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[cH:26][cH:25]1.C[O:19][C:17]([c:16]1[cH:15][c:14]([CH2:13][O:12][c:11]2[cH:10][cH:9][c:8](I)[cH:24][cH:23]2)[c:21]([CH3:22])[o:20]1)=[O:18]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([O:12][CH2:13][c:14]3[cH:15][c:16]([C:17](=[O:18])[OH:19])[... | CCOc1ccc(B(O)O)cc1.COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1 | CCOc1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)cc1 | null | null | null | C-C Coupling | OtherReaction | 04157bef51d5543c035526858b11d2af2b78e75d38cd85edf56b617e6aebc946 | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2ccc(OCc3ccoc3)cc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#8;a:5].I-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10].O-B(-O)-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]>>[#8;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1].[c:10]:[c:9]:[c;H0;D3;+0:6](-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]):[c:7]:[c:8] | null | [] | null | null | null | null | Compound (98) was prepared from compound (20) and (4-ethoxyphenyl)-boronic acid by an adapting the procedure of Example 24A. LC/MS System B; Rt=1.86 mins, m/z (ES−) 351 (M−H for C21H20O5).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccoc1 | HI.B | null | null | null | CCOc1ccc(B(O)O)cc1.COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1>>CCOc1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f0d31306041240e0a3ebdf610ed46d30 | COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1.OB(O)c1ccccc1Cl>>Cc1oc(C(=O)O)cc1COc1ccc(-c2ccccc2Cl)cc1 | COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)I)C.ClC1=C(C=CC=C1)B(O)O>>ClC1=C(C=CC=C1)C1=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)O | C[O:7][C:5]([c:4]1[o:3][c:2]([CH3:1])[c:9]([CH2:10][O:11][c:12]2[cH:13][cH:14][c:15](I)[cH:23][cH:24]2)[cH:8]1)=[O:6].OB(O)[c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[Cl:22]>>[CH3:1][c:2]1[o:3][c:4]([C:5](=[O:6])[OH:7])[cH:8][c:9]1[CH2:10][O:11][c:12]1[cH:13][cH:14][c:15](-[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[Cl:2... | COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1.OB(O)c1ccccc1Cl | Cc1oc(C(=O)O)cc1COc1ccc(-c2ccccc2Cl)cc1 | null | null | null | C-C Coupling | OtherReaction | 04157bef51d5543c035526858b11d2af2b78e75d38cd85edf56b617e6aebc946 | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2ccc(OCc3ccoc3)cc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#8;a:5].I-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10].O-B(-O)-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14](-[Cl;D1;H0:15]):[c:16]>>[#8;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1].[Cl;D1;H0:15]-[c:14](:[c:16]):[c;H0;D3;+0:11](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:12]:[c:13] | null | [] | null | null | null | null | Compound (99) was prepared from compound (20) and (2-chlorophenyl)-boronic acid by adapting the procedure of Example 5(b). LC/MS System B; Rt=1.86 mins, m/z (ES−)=341 and 343 (M−H for C19H15ClO4).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccoc1.c1ccccc1.c1ccccc1 | HI.B | null | null | null | COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1.OB(O)c1ccccc1Cl>>Cc1oc(C(=O)O)cc1COc1ccc(-c2ccccc2Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-28dbdc5ae2cc4f0c8a4912c54813641b | COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1.OB(O)c1c(F)cccc1F>>Cc1oc(C(=O)O)cc1COc1ccc(-c2c(F)cccc2F)cc1 | COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)I)C.FC1=C(C(=CC=C1)F)B(O)O>>FC1=C(C(=CC=C1)F)C1=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)O | C[O:7][C:5]([c:4]1[o:3][c:2]([CH3:1])[c:9]([CH2:10][O:11][c:12]2[cH:13][cH:14][c:15](I)[cH:24][cH:25]2)[cH:8]1)=[O:6].OB(O)[c:16]1[c:17]([F:18])[cH:19][cH:20][cH:21][c:22]1[F:23]>>[CH3:1][c:2]1[o:3][c:4]([C:5](=[O:6])[OH:7])[cH:8][c:9]1[CH2:10][O:11][c:12]1[cH:13][cH:14][c:15](-[c:16]2[c:17]([F:18])[cH:19][cH:20][cH:21... | COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1.OB(O)c1c(F)cccc1F | Cc1oc(C(=O)O)cc1COc1ccc(-c2c(F)cccc2F)cc1 | null | null | null | C-C Coupling | OtherReaction | 04157bef51d5543c035526858b11d2af2b78e75d38cd85edf56b617e6aebc946 | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2ccc(OCc3ccoc3)cc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#8;a:5].I-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10].O-B(-O)-[c;H0;D3;+0:11](:[c:12](-[F;D1;H0:13]):[c:14]):[c:15](-[F;D1;H0:16]):[c:17]>>[#8;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1].[F;D1;H0:13]-[c:12](:[c:14]):[c;H0;D3;+0:11](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c... | null | [] | null | null | null | null | Compound (100) was prepared from compound (20) and (2,6-difluorophenyl)-boronic acid by adapting the procedure of Example 5(b). LC/MS System B; Rt=1.83 mins, m/z (ES−)=343 (M−H for C19H14F2O4).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccoc1.c1ccccc1.c1ccccc1 | HI.B | null | null | null | COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1.OB(O)c1c(F)cccc1F>>Cc1oc(C(=O)O)cc1COc1ccc(-c2c(F)cccc2F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cc13d83cc9ed4a93a4e80f4f170d6d88 | COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1.OB(O)c1ccccc1C(F)(F)F>>Cc1oc(C(=O)O)cc1COc1ccc(-c2ccccc2C(F)(F)F)cc1 | COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)I)C.FC(C1=C(C=CC=C1)B(O)O)(F)F>>CC1=C(C=C(O1)C(=O)O)COC1=CC=C(C=C1)C1=C(C=CC=C1)C(F)(F)F | C[O:7][C:5]([c:4]1[o:3][c:2]([CH3:1])[c:9]([CH2:10][O:11][c:12]2[cH:13][cH:14][c:15](I)[cH:26][cH:27]2)[cH:8]1)=[O:6].OB(O)[c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[C:22]([F:23])([F:24])[F:25]>>[CH3:1][c:2]1[o:3][c:4]([C:5](=[O:6])[OH:7])[cH:8][c:9]1[CH2:10][O:11][c:12]1[cH:13][cH:14][c:15](-[c:16]2[cH:17][cH:18][cH:1... | COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1.OB(O)c1ccccc1C(F)(F)F | Cc1oc(C(=O)O)cc1COc1ccc(-c2ccccc2C(F)(F)F)cc1 | null | null | null | C-C Coupling | OtherReaction | 04157bef51d5543c035526858b11d2af2b78e75d38cd85edf56b617e6aebc946 | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2ccc(OCc3ccoc3)cc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#8;a:5].I-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10].O-B(-O)-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14](-[C:15](-[F;D1;H0:16])(-[F;D1;H0:17])-[F;D1;H0:18]):[c:19]>>[#8;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1].[F;D1;H0:16]-[C:15](-[F;D1;H0:17])(-[F;D1;H0:18])-[c:14](:[c:19]):[c;... | null | [] | null | null | null | null | Compound (102) was prepared from compound (20) and (2-trifluoromethyl-phenyl)-boronic acid by adapting the procedure of Example 5(b). LC/MS System B; Rt=1.93 mins, m/z (ES−)=375 (M−H for C20H15F3O4).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccoc1.c1ccccc1.c1ccccc1 | HI.B | null | null | null | COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1.OB(O)c1ccccc1C(F)(F)F>>Cc1oc(C(=O)O)cc1COc1ccc(-c2ccccc2C(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a327e610d9b4437480c441c754af1547 | COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1.OB(O)c1ccc(Cl)cc1>>O=C(O)c1cc(COc2ccc(-c3ccccc3)cc2)co1 | COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)I)C.ClC1=CC=C(C=C1)B(O)O>>C1(=CC=C(C=C1)OCC=1C=C(OC1)C(=O)O)C1=CC=CC=C1 | C[O:3][C:2](=[O:1])[c:4]1[cH:5][c:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12](I)[cH:19][cH:20]2)[c:21](C)[o:22]1.OB(O)[c:13]1[cH:14][cH:15][c:16](Cl)[cH:17][cH:18]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19][cH:20]2)[cH:21][o:22]1 | COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1.OB(O)c1ccc(Cl)cc1 | O=C(O)c1cc(COc2ccc(-c3ccccc3)cc2)co1 | null | null | null | C-C Coupling | OtherReaction | 208d7cb8553b4a8de62b809cfc13cdf69831a49eaa82f1183e0589cc9f7bb8ce | 57e36285fe5e46d1b7fb6bd126f751f9e7245cbcf73856b9176889fbc17d553c | c1ccc(-c2ccc(OCc3ccoc3)cc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[#8;a:5]:[c;H0;D3;+0:6](-C):[c:7](-[C:8]):[c:9]:1.I-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14].Cl-[c;H0;D3;+0:15]1:[c:16]:[c:17]:[c;H0;D3;+0:18](-B(-O)-O):[c:19]:[c:20]:1>>[C:8]-[c:7]1:[c:9]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[#8;a:5]:[cH;D2;+0:6]:1.[c:12]:[c:11]:[c;... | null | [] | null | null | null | null | Compound (77) was prepared from compound (20) and (4-chloro-phenyl)-boronic acid by adapting the procedure of Example 5(b). LC/MS System B; Rt=1.93 mins, m/z (ES−)=341 and 343 (M−H for C19H15ClO4).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1ccoc1.c1ccccc1.c1ccccc1 | c1ccoc1.c1ccccc1.c1ccccc1 | c1ccoc1.c1ccccc1.c1ccccc1 | HCl.I-.B | null | null | null | COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1.OB(O)c1ccc(Cl)cc1>>O=C(O)c1cc(COc2ccc(-c3ccccc3)cc2)co1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8577508583384178b30a1ef53df52204 | COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1.OB(O)c1cccc(F)c1>>Cc1oc(C(=O)O)cc1COc1ccc(-c2cccc(F)c2)cc1 | COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)I)C.FC=1C=C(C=CC1)B(O)O>>FC=1C=C(C=CC1)C1=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)O | C[O:7][C:5]([c:4]1[o:3][c:2]([CH3:1])[c:9]([CH2:10][O:11][c:12]2[cH:13][cH:14][c:15](I)[cH:23][cH:24]2)[cH:8]1)=[O:6].OB(O)[c:16]1[cH:17][cH:18][cH:19][c:20]([F:21])[cH:22]1>>[CH3:1][c:2]1[o:3][c:4]([C:5](=[O:6])[OH:7])[cH:8][c:9]1[CH2:10][O:11][c:12]1[cH:13][cH:14][c:15](-[c:16]2[cH:17][cH:18][cH:19][c:20]([F:21])[cH:... | COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1.OB(O)c1cccc(F)c1 | Cc1oc(C(=O)O)cc1COc1ccc(-c2cccc(F)c2)cc1 | null | null | null | C-C Coupling | OtherReaction | 04157bef51d5543c035526858b11d2af2b78e75d38cd85edf56b617e6aebc946 | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2ccc(OCc3ccoc3)cc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#8;a:5].I-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10].O-B(-O)-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]>>[#8;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1].[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]):[c:9]:[c:10] | null | [] | null | null | null | null | Compound (104) was prepared from compound (20) and (3-fluoro-phenyl)-boronic acid by adapting the procedure of Example 5(b). LC/MS System B; Rt=1.83 mins, m/z (ES−)=325 (M−H for C19H15FO4).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccoc1.c1ccccc1.c1ccccc1 | HI.B | null | null | null | COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1.OB(O)c1cccc(F)c1>>Cc1oc(C(=O)O)cc1COc1ccc(-c2cccc(F)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-01bea476d7a24691adbcc38b526e3118 | COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1.CSc1ccccc1B(O)O>>CSc1ccccc1-c1ccc(OCc2cc(C(=O)O)oc2C)cc1 | COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)I)C.CSC1=C(C=CC=C1)B(O)O>>CC1=C(C=C(O1)C(=O)O)COC1=CC=C(C=C1)C1=C(C=CC=C1)SC | C[O:20][C:18]([c:17]1[cH:16][c:15]([CH2:14][O:13][c:12]2[cH:11][cH:10][c:9](I)[cH:25][cH:24]2)[c:22]([CH3:23])[o:21]1)=[O:19].OB(O)[c:8]1[c:3]([S:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[c:9]1[cH:10][cH:11][c:12]([O:13][CH2:14][c:15]2[cH:16][c:17]([C:18](=[O:19])[OH:20])[o:... | COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1.CSc1ccccc1B(O)O | CSc1ccccc1-c1ccc(OCc2cc(C(=O)O)oc2C)cc1 | null | null | null | C-C Coupling | OtherReaction | 04157bef51d5543c035526858b11d2af2b78e75d38cd85edf56b617e6aebc946 | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2ccc(OCc3ccoc3)cc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#8;a:5].I-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10].O-B(-O)-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14](-[#16:15]):[c:16]>>[#16:15]-[c:14](:[c:16]):[c;H0;D3;+0:11](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:12]:[c:13].[#8;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | null | null | Compound (105) was prepared from compound (20) and (2-methylsulphanyl-phenyl)-boronic acid by adapting the procedure of Example 5(b). LC/MS System B; Rt=1.86 mins, m/z (ES−)=353 (M−H for C20H18O4S).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccoc1 | HI.B | null | null | null | COC(=O)c1cc(COc2ccc(I)cc2)c(C)o1.CSc1ccccc1B(O)O>>CSc1ccccc1-c1ccc(OCc2cc(C(=O)O)oc2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3d6ea64c5ed048f68628e533251ab5c5 | COC(=O)c1cc(CO)c(C)o1.Oc1cccc(I)c1>>COC(=O)c1cc(COc2cccc(I)c2)c(C)o1 | CC(C)OC(=O)/N=N/C(=O)OC(C)C.COC(=O)C=1OC(=C(C1)CO)C.IC=1C=C(C=CC1)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>COC(=O)C=1OC(=C(C1)COC1=CC(=CC=C1)I)C | O[CH2:8][c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[o:19][c:17]1[CH3:18].[OH:9][c:10]1[cH:11][cH:12][cH:13][c:14]([I:15])[cH:16]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][O:9][c:10]2[cH:11][cH:12][cH:13][c:14]([I:15])[cH:16]2)[c:17]([CH3:18])[o:19]1 | COC(=O)c1cc(CO)c(C)o1.Oc1cccc(I)c1 | COC(=O)c1cc(COc2cccc(I)c2)c(C)o1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(OCc2ccoc2)cc1 | O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4](-[C:5](-[#8:6])=[O;D1;H0:7]):[#8;a:8]:[c:9]:1-[C;D1;H3:10].[OH;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]1:[#8;a:8]:[c:9](-[C;D1;H3:10]):[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:3]:1 | 69 | [{"value": 69.0, "product": "COC(=O)C=1OC(=C(C1)COC1=CC(=CC=C1)I)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 72 | HOUR | A mixture of 4-hydroxymethyl-5-methyl-furan-2-carboxylic acid methyl ester (16) (1.85 g, 10.9 mmoles), 3-iodophenol (3.6 g, 16.35 mmoles), triphenylphosphine (4.3 g, 16.35 mmoles) in tetrahydrofuran (15 mL) was cooled to 0° C. Diisopropylazodicarboxylate (3.3 g, 16.35 mmoles) was added and the mixture was allowed to wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccoc1.c1ccccc1 | HO- | O1CCCC1 | 0 | 72 | COC(=O)c1cc(CO)c(C)o1.Oc1cccc(I)c1>O1CCCC1>COC(=O)c1cc(COc2cccc(I)c2)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4a2158331057488e93cfd7699c144d36 | COC(=O)c1cc(COc2cccc(I)c2)c(C)o1>>Cc1oc(C(=O)O)cc1COc1cccc(I)c1 | COC(=O)C=1OC(=C(C1)COC1=CC(=CC=C1)I)C.[OH-].[Li+].O>>IC=1C=C(OCC=2C=C(OC2C)C(=O)O)C=CC1 | C[O:7][C:5]([c:4]1[o:3][c:2]([CH3:1])[c:9]([CH2:10][O:11][c:12]2[cH:13][cH:14][cH:15][c:16]([I:17])[cH:18]2)[cH:8]1)=[O:6]>>[CH3:1][c:2]1[o:3][c:4]([C:5](=[O:6])[OH:7])[cH:8][c:9]1[CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][c:16]([I:17])[cH:18]1 | COC(=O)c1cc(COc2cccc(I)c2)c(C)o1 | Cc1oc(C(=O)O)cc1COc1cccc(I)c1 | null | null | O1CCCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(OCc2ccoc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#8;a:5]>>[#8;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 67.8 | [{"value": 67.8, "product": "IC=1C=C(OCC=2C=C(OC2C)C(=O)O)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A mixture of 4-(3-iodo-phenoxymethyl)-5-methyl-furan-2-carboxylic acid methyl ester (106) (2.7 g, 7.25 mmoles) and lithium hydroxide (1.5 g, 36.25 mmoles) in tetrahydrofuran (25 ml) containing water (2 ml) was stirred at room temperature for 3 h. The tetrahydrofuran was evaporated, the residue was diluted with water an... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccoc1.c1ccccc1 | Other | O1CCCC1 | null | 3 | COC(=O)c1cc(COc2cccc(I)c2)c(C)o1>O1CCCC1>Cc1oc(C(=O)O)cc1COc1cccc(I)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1e64fadabc8040509211bab2ca1d8aa8 | Cc1oc(C(=O)O)cc1COc1cccc(I)c1.OB(O)c1cccc(C(F)(F)F)c1>>Cc1oc(C(=O)O)cc1COc1cccc(-c2cccc(C(F)(F)F)c2)c1 | IC=1C=C(OCC=2C=C(OC2C)C(=O)O)C=CC1.FC(C=1C=C(C=CC1)B(O)O)(F)F>>CC1=C(C=C(O1)C(=O)O)COC=1C=C(C=CC1)C1=CC(=CC=C1)C(F)(F)F | I[c:16]1[cH:15][cH:14][cH:13][c:12]([O:11][CH2:10][c:9]2[c:2]([CH3:1])[o:3][c:4]([C:5](=[O:6])[OH:7])[cH:8]2)[cH:27]1.OB(O)[c:17]1[cH:18][cH:19][cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[cH:26]1>>[CH3:1][c:2]1[o:3][c:4]([C:5](=[O:6])[OH:7])[cH:8][c:9]1[CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][c:16](-[c:17]2[cH:18][cH... | Cc1oc(C(=O)O)cc1COc1cccc(I)c1.OB(O)c1cccc(C(F)(F)F)c1 | Cc1oc(C(=O)O)cc1COc1cccc(-c2cccc(C(F)(F)F)c2)c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccc(OCc3ccoc3)c2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:2]:[c:3] | null | [] | null | null | null | null | Compound (109) was prepared from compound (107) and (3-trifluoromethyl-phenyl)-boronic acid by adapting the procedure of Example 26A(c). LC/MS System B; Rt=1.97 mins, m/z (ES−)=375 (M−H for C20H15F3O4).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccoc1.c1ccccc1.c1ccccc1 | HI.B | null | null | null | Cc1oc(C(=O)O)cc1COc1cccc(I)c1.OB(O)c1cccc(C(F)(F)F)c1>>Cc1oc(C(=O)O)cc1COc1cccc(-c2cccc(C(F)(F)F)c2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-92ddf5af190d4c29a69761cabcfddae3 | Cc1oc(C(=O)O)cc1COc1ccc(I)cc1.OB(O)c1cccc(O)c1>>Cc1oc(C(=O)O)cc1COc1ccc(-c2cccc(O)c2)cc1 | IC1=CC=C(OCC=2C=C(OC2C)C(=O)O)C=C1.OC=1C=C(C=CC1)B(O)O>>OC=1C=C(C=CC1)C1=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)O | I[c:15]1[cH:14][cH:13][c:12]([O:11][CH2:10][c:9]2[c:2]([CH3:1])[o:3][c:4]([C:5](=[O:6])[OH:7])[cH:8]2)[cH:24][cH:23]1.OB(O)[c:16]1[cH:17][cH:18][cH:19][c:20]([OH:21])[cH:22]1>>[CH3:1][c:2]1[o:3][c:4]([C:5](=[O:6])[OH:7])[cH:8][c:9]1[CH2:10][O:11][c:12]1[cH:13][cH:14][c:15](-[c:16]2[cH:17][cH:18][cH:19][c:20]([OH:21])[c... | Cc1oc(C(=O)O)cc1COc1ccc(I)cc1.OB(O)c1cccc(O)c1 | Cc1oc(C(=O)O)cc1COc1ccc(-c2cccc(O)c2)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc(OCc3ccoc3)cc2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | null | [] | null | null | null | null | Compound (112) was prepared from compound (26) and (3-hydroxy-phenyl)-boronic acid by adapting the procedure of Example 27A. LC/MS System B; Rt=1.23 mins, m/z (ES−)=323 (M−H for C19H16O5).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccoc1.c1ccccc1.c1ccccc1 | HI.B | null | null | null | Cc1oc(C(=O)O)cc1COc1ccc(I)cc1.OB(O)c1cccc(O)c1>>Cc1oc(C(=O)O)cc1COc1ccc(-c2cccc(O)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c93c2c2b2c82485bbc72c0e49d1a1560 | CN(C)c1ccc(B(O)O)cc1.Cc1oc(C(=O)O)cc1COc1ccc(I)cc1>>Cc1oc(C(=O)O)cc1COc1ccc(-c2ccc(N(C)C)cc2)cc1 | IC1=CC=C(OCC=2C=C(OC2C)C(=O)O)C=C1.CN(C1=CC=C(C=C1)B(O)O)C>>CN(C1=CC=C(C=C1)C1=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)O)C | OB(O)[c:16]1[cH:17][cH:18][c:19]([N:20]([CH3:21])[CH3:22])[cH:23][cH:24]1.I[c:15]1[cH:14][cH:13][c:12]([O:11][CH2:10][c:9]2[c:2]([CH3:1])[o:3][c:4]([C:5](=[O:6])[OH:7])[cH:8]2)[cH:26][cH:25]1>>[CH3:1][c:2]1[o:3][c:4]([C:5](=[O:6])[OH:7])[cH:8][c:9]1[CH2:10][O:11][c:12]1[cH:13][cH:14][c:15](-[c:16]2[cH:17][cH:18][c:19](... | CN(C)c1ccc(B(O)O)cc1.Cc1oc(C(=O)O)cc1COc1ccc(I)cc1 | Cc1oc(C(=O)O)cc1COc1ccc(-c2ccc(N(C)C)cc2)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc(OCc3ccoc3)cc2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | null | [] | null | null | null | null | Compound (113) was prepared from compound (26) and (4-dimethylamino-phenyl)-boronic acid by adapting the procedure of Example 27B. LC/MS System B; Rt=1.83 mins, m/z (ES−)=350 (M−H for C21H21NO4).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccoc1.c1ccccc1.c1ccccc1 | HI.B | null | null | null | CN(C)c1ccc(B(O)O)cc1.Cc1oc(C(=O)O)cc1COc1ccc(I)cc1>>Cc1oc(C(=O)O)cc1COc1ccc(-c2ccc(N(C)C)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7035b38a01324b5d8ca19f4b9f3ffd87 | Cc1oc(C(=O)O)cc1COc1ccc(I)cc1.OB(O)c1ccc(OC(F)(F)F)cc1>>Cc1oc(C(=O)O)cc1COc1ccc(-c2ccc(OC(F)(F)F)cc2)cc1 | IC1=CC=C(OCC=2C=C(OC2C)C(=O)O)C=C1.FC(OC1=CC=C(C=C1)B(O)O)(F)F>>CC1=C(C=C(O1)C(=O)O)COC1=CC=C(C=C1)C1=CC=C(C=C1)OC(F)(F)F | I[c:15]1[cH:14][cH:13][c:12]([O:11][CH2:10][c:9]2[c:2]([CH3:1])[o:3][c:4]([C:5](=[O:6])[OH:7])[cH:8]2)[cH:28][cH:27]1.OB(O)[c:16]1[cH:17][cH:18][c:19]([O:20][C:21]([F:22])([F:23])[F:24])[cH:25][cH:26]1>>[CH3:1][c:2]1[o:3][c:4]([C:5](=[O:6])[OH:7])[cH:8][c:9]1[CH2:10][O:11][c:12]1[cH:13][cH:14][c:15](-[c:16]2[cH:17][cH:... | Cc1oc(C(=O)O)cc1COc1ccc(I)cc1.OB(O)c1ccc(OC(F)(F)F)cc1 | Cc1oc(C(=O)O)cc1COc1ccc(-c2ccc(OC(F)(F)F)cc2)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc(OCc3ccoc3)cc2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | null | [] | null | null | null | null | Compound (114) was prepared from compound (26) and (4-trifluoromethoxy-phenyl)-boronic acid by adapting the procedure of Example 27B. LC/MS System C; Rt=11.01 mins, m/z (ES−)=391 (M−H for C20H15F3O5).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccoc1.c1ccccc1.c1ccccc1 | HI.B | null | null | null | Cc1oc(C(=O)O)cc1COc1ccc(I)cc1.OB(O)c1ccc(OC(F)(F)F)cc1>>Cc1oc(C(=O)O)cc1COc1ccc(-c2ccc(OC(F)(F)F)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a445ee1ffded4aad94a53923cae7e2c0 | Cc1oc(C(=O)O)cc1COc1ccc(I)cc1.OB(O)c1ccccc1OC(F)(F)F>>Cc1oc(C(=O)O)cc1COc1ccc(-c2ccccc2OC(F)(F)F)cc1 | IC1=CC=C(OCC=2C=C(OC2C)C(=O)O)C=C1.FC(OC1=C(C=CC=C1)B(O)O)(F)F>>CC1=C(C=C(O1)C(=O)O)COC1=CC=C(C=C1)C1=C(C=CC=C1)OC(F)(F)F | I[c:15]1[cH:14][cH:13][c:12]([O:11][CH2:10][c:9]2[c:2]([CH3:1])[o:3][c:4]([C:5](=[O:6])[OH:7])[cH:8]2)[cH:28][cH:27]1.OB(O)[c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[O:22][C:23]([F:24])([F:25])[F:26]>>[CH3:1][c:2]1[o:3][c:4]([C:5](=[O:6])[OH:7])[cH:8][c:9]1[CH2:10][O:11][c:12]1[cH:13][cH:14][c:15](-[c:16]2[cH:17][cH:18... | Cc1oc(C(=O)O)cc1COc1ccc(I)cc1.OB(O)c1ccccc1OC(F)(F)F | Cc1oc(C(=O)O)cc1COc1ccc(-c2ccccc2OC(F)(F)F)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc(OCc3ccoc3)cc2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[#8:10]):[c:11]>>[#8:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | null | [] | null | null | null | null | Compound (115) was prepared from compound (26) and (2-trifluoromethoxy-phenyl)-boronic acid by adapting the procedure of Example 27B. LC/MS System B; Rt=1.97 mins, m/z (ES−)=391 (M−H for C20H15F3O5).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccoc1.c1ccccc1.c1ccccc1 | HI.B | null | null | null | Cc1oc(C(=O)O)cc1COc1ccc(I)cc1.OB(O)c1ccccc1OC(F)(F)F>>Cc1oc(C(=O)O)cc1COc1ccc(-c2ccccc2OC(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a745ebe2cec542bea3f976d0ccc14e07 | COc1cccc(B(O)O)c1.Cc1oc(C(=O)O)cc1COc1ccc(I)cc1>>COc1cccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)c1 | IC1=CC=C(OCC=2C=C(OC2C)C(=O)O)C=C1.COC=1C=C(C=CC1)B(O)O>>COC=1C=C(C=CC1)C1=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)O | OB(O)[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:25]1.I[c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][c:14]2[cH:15][c:16]([C:17](=[O:18])[OH:19])[o:20][c:21]2[CH3:22])[cH:23][cH:24]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([O:12][CH2:13][c:14]3[cH:15][c:16]([C:17](=[O:18])[OH:19])[o:20][c:21]... | COc1cccc(B(O)O)c1.Cc1oc(C(=O)O)cc1COc1ccc(I)cc1 | COc1cccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc(OCc3ccoc3)cc2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:2]:[c:3] | null | [] | null | null | null | null | Compound (116) was prepared from compound (26) and (3-methoxy-phenyl)-boronic acid by adapting the procedure of Example 27B. LC/MS System B; Rt=1.79 mins, m/z (ES−)=337 (M−H for C20H18O5).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccoc1 | HI.B | null | null | null | COc1cccc(B(O)O)c1.Cc1oc(C(=O)O)cc1COc1ccc(I)cc1>>COc1cccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-75029e6729194d0fb444b8fba2204342 | CC(=O)c1cccc(B(O)O)c1.Cc1oc(C(=O)O)cc1COc1ccc(I)cc1>>CC(=O)c1cccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)c1 | IC1=CC=C(OCC=2C=C(OC2C)C(=O)O)C=C1.C(C)(=O)C=1C=C(C=CC1)B(O)O>>C(C)(=O)C=1C=C(C=CC1)C1=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)O | OB(O)[c:8]1[cH:7][cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:26]1.I[c:9]1[cH:10][cH:11][c:12]([O:13][CH2:14][c:15]2[cH:16][c:17]([C:18](=[O:19])[OH:20])[o:21][c:22]2[CH3:23])[cH:24][cH:25]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([O:13][CH2:14][c:15]3[cH:16][c:17]([C:18](=[O:19])[O... | CC(=O)c1cccc(B(O)O)c1.Cc1oc(C(=O)O)cc1COc1ccc(I)cc1 | CC(=O)c1cccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc(OCc3ccoc3)cc2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]-[C:9](-[C;D1;H3:10])=[O;D1;H0:11]):[c:12]:[c:13]>>[C;D1;H3:10]-[C:9](=[O;D1;H0:11])-[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:12]:[c:13] | null | [] | null | null | null | null | Compound (117) was prepared from compound (26) and (3-acetyl-phenyl)-boronic acid by adapting the procedure of Example 27B. LC/MS System B; Rt=1.69 mins, m/z (ES−) 349 (M−H for C21H18O5).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccoc1 | HI.B | null | null | null | CC(=O)c1cccc(B(O)O)c1.Cc1oc(C(=O)O)cc1COc1ccc(I)cc1>>CC(=O)c1cccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9c103d1d8e37431983902d7095198680 | Cc1oc(C(=O)O)cc1COc1ccc(I)cc1.OB(O)c1ccc(F)cc1>>Cc1oc(C(=O)O)cc1COc1ccc(-c2ccc(F)cc2)cc1 | IC1=CC=C(OCC=2C=C(OC2C)C(=O)O)C=C1.FC1=CC=C(C=C1)B(O)O>>FC1=CC=C(C=C1)C1=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)O | I[c:15]1[cH:14][cH:13][c:12]([O:11][CH2:10][c:9]2[c:2]([CH3:1])[o:3][c:4]([C:5](=[O:6])[OH:7])[cH:8]2)[cH:24][cH:23]1.OB(O)[c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]1>>[CH3:1][c:2]1[o:3][c:4]([C:5](=[O:6])[OH:7])[cH:8][c:9]1[CH2:10][O:11][c:12]1[cH:13][cH:14][c:15](-[c:16]2[cH:17][cH:18][c:19]([F:20])[cH:21][cH:... | Cc1oc(C(=O)O)cc1COc1ccc(I)cc1.OB(O)c1ccc(F)cc1 | Cc1oc(C(=O)O)cc1COc1ccc(-c2ccc(F)cc2)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc(OCc3ccoc3)cc2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | null | [] | null | null | null | null | Compound (118) was prepared from compound (26) and (4-fluoro-phenyl)-boronic acid by adapting the procedure of Example 27B. LC/MS System B; Rt=1.79 mins, m/z (ES−)=325 (M−H for C19H15FO4).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccoc1.c1ccccc1.c1ccccc1 | HI.B | null | null | null | Cc1oc(C(=O)O)cc1COc1ccc(I)cc1.OB(O)c1ccc(F)cc1>>Cc1oc(C(=O)O)cc1COc1ccc(-c2ccc(F)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-210eee0a1b654d54865c2dd8538b0772 | CN(C)S(N)(=O)=O.COc1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)cc1>>COc1ccc(-c2ccc(OCc3cc(C(=O)NS(=O)(=O)N(C)C)oc3C)cc2)cc1 | CN(S(=O)(=O)N)C.Cl.CN(CCCN=C=NCC)C.COC1=CC=C(C=C1)C1=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)O>>COC1=CC=C(C=C1)C1=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)NS(=O)(=O)N(C)C | [NH2:18][S:19](=[O:20])(=[O:21])[N:22]([CH3:23])[CH3:24].O[C:16]([c:15]1[cH:14][c:13]([CH2:12][O:11][c:10]2[cH:9][cH:8][c:7](-[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:31][cH:30]3)[cH:29][cH:28]2)[c:26]([CH3:27])[o:25]1)=[O:17]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([O:11][CH2:12][c:13]3[cH:14][c... | CN(C)S(N)(=O)=O.COc1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)cc1 | COc1ccc(-c2ccc(OCc3cc(C(=O)NS(=O)(=O)N(C)C)oc3C)cc2)cc1 | null | CN(C1=CC=NC=C1)C | ClCCl | Acylation | Carboxylic acid with primary amine to amide | 195a412a8235704efe2985cdc18467ba661e632bab7b61944399ecc813e32a09 | 5e4665bad9c6f58dddd98c5f95e436c640b4c0118b04efea5cd58c7d1755401d | c1ccc(-c2ccc(OCc3ccoc3)cc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[#7:7]-[#16:8](-[NH2;D1;+0:9])(=[O;D1;H0:10])=[O;D1;H0:11]>>[#7:7]-[#16:8](=[O;D1;H0:10])(=[O;D1;H0:11])-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6] | 35.7 | [{"value": 35.7, "product": "COC1=CC=C(C=C1)C1=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)NS(=O)(=O)N(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | N,N-Dimethylsulphamide (73 mg, 0.59 mmoles), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (31 mg, 0.162 mmoles) and dimethyl-pyridin-4-yl-amine (1 mg) were added to a stirred solution of 4-(4′-methoxy-biphenyl-4-yloxymethyl)-5-methyl-furan-2-carboxylic acid (4) (50 mg, 0.148 mmoles) in dichloromethane ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Carboxylic acid | Sulfonamide.Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccoc1 | HO- | CN(C1=CC=NC=C1)C.ClCCl | null | 18 | CN(C)S(N)(=O)=O.COc1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)cc1>CN(C1=CC=NC=C1)C.ClCCl>COc1ccc(-c2ccc(OCc3cc(C(=O)NS(=O)(=O)N(C)C)oc3C)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b70a8f12d1c243739b8e0a7b71a61923 | Cc1occc1CO.Oc1ccc(I)cc1>>Cc1occc1COc1ccc(I)cc1 | CC=1OC=CC1CO.IC1=CC=C(C=C1)O>>IC1=CC=C(OCC2=C(OC=C2)C)C=C1 | O[CH2:7][c:6]1[c:2]([CH3:1])[o:3][cH:4][cH:5]1.[OH:8][c:9]1[cH:10][cH:11][c:12]([I:13])[cH:14][cH:15]1>>[CH3:1][c:2]1[o:3][cH:4][cH:5][c:6]1[CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([I:13])[cH:14][cH:15]1 | Cc1occc1CO.Oc1ccc(I)cc1 | Cc1occc1COc1ccc(I)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(OCc2ccoc2)cc1 | O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#8;a:5]:[c:6]:1-[C;D1;H3:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:7]-[c:6]1:[#8;a:5]:[c:4]:[c:3]:[c:2]:1-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | 3-(4-Iodo-phenoxymethyl)-2-methyl-furan was prepared from (2-methyl-furan-3-yl)-methanol and 4-iodo-phenol in an analogous manner to that described in Example 14(a).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccoc1.c1ccccc1 | HO- | null | null | null | Cc1occc1CO.Oc1ccc(I)cc1>>Cc1occc1COc1ccc(I)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-30912a3d6da24e659691cf8a35221043 | Cc1occc1COc1ccc(I)cc1.OB(O)c1ccc(F)cc1>>Cc1occc1COc1ccc(-c2ccc(F)cc2)cc1 | FC1=CC=C(C=C1)B(O)O.IC1=CC=C(OCC2=C(OC=C2)C)C=C1.C(C)(=O)[O-].[K+]>>FC1=CC=C(C=C1)C1=CC=C(C=C1)OCC1=C(OC=C1)C | I[c:12]1[cH:11][cH:10][c:9]([O:8][CH2:7][c:6]2[c:2]([CH3:1])[o:3][cH:4][cH:5]2)[cH:21][cH:20]1.OB(O)[c:13]1[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]1>>[CH3:1][c:2]1[o:3][cH:4][cH:5][c:6]1[CH2:7][O:8][c:9]1[cH:10][cH:11][c:12](-[c:13]2[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]2)[cH:20][cH:21]1 | Cc1occc1COc1ccc(I)cc1.OB(O)c1ccc(F)cc1 | Cc1occc1COc1ccc(-c2ccc(F)cc2)cc1 | null | null | CN(C=O)C | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc(OCc3ccoc3)cc2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 44.3 | [{"value": 44.3, "product": "FC1=CC=C(C=C1)C1=CC=C(C=C1)OCC1=C(OC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | 12 | HOUR | A mixture of (4-fluoro-phenyl)-boronic acid (300 mg, 2.1 mmoles), 3-(4-iodophenoxymethyl)-2-methyl-furan (123) (500 mg, 1.6 mmoles) and potassium acetate (0.6 g) in N,N-dimethylformamide (70 mL) was degassed, treated with [1,1′-bis(diphenylphosphino) ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (9... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccoc1.c1ccccc1.c1ccccc1 | HI.B | CN(C=O)C | 95 | 12 | Cc1occc1COc1ccc(I)cc1.OB(O)c1ccc(F)cc1>CN(C=O)C>Cc1occc1COc1ccc(-c2ccc(F)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7fb2007ee68c4b29b71708a42bf794c5 | COC(=O)c1cc(COc2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c(C)o1.COc1ccccc1Br>>COC(=O)c1cc(COc2ccc(-c3ccccc3OC)cc2)c(C)o1 | COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)B1OC(C(O1)(C)C)(C)C)C.BrC1=C(C=CC=C1)OC.C([O-])([O-])=O.[Cs+].[Cs+].ClCCl>>COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)C1=C(C=CC=C1)OC)C | CC1(C)OB([c:13]2[cH:12][cH:11][c:10]([O:9][CH2:8][c:7]3[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[o:26][c:24]3[CH3:25])[cH:23][cH:22]2)OC1(C)C.Br[c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[O:20][CH3:21]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][O:9][c:10]2[cH:11][cH:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][cH:18][c... | COC(=O)c1cc(COc2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c(C)o1.COc1ccccc1Br | COC(=O)c1cc(COc2ccc(-c3ccccc3OC)cc2)c(C)o1 | null | null | O1CCOCC1 | C-C Coupling | Suzuki coupling with boronic esters | 8b44d63590c7228953eb9acb565338c9584155fdcec14c37f9f3f344e065dc2d | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | c1ccc(-c2ccc(OCc3ccoc3)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#8:5]):[c:6].C-C1(-C)-O-B(-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11])-O-C-1(-C)-C>>[#8:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]):[c:2]:[c:3] | 21 | [{"value": 21.0, "product": "COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)C1=C(C=CC=C1)OC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A degassed mixture of 5-methyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxymethyl]-furan-2-carboxylic acid methyl ester (119) (200 mg, 0.54 mmoles), 1-bromo-2-methoxy-benzene (80 μl, 0.65 mmoles), 2M aqueous cesium carbonate (11.0 ml) and), [1,1′-bis(diphenylphosphino) ferrocene]dichloropalladium(II) com... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | B1OCCO1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccoc1.c1ccccc1.c1ccccc1 | HBr.B | O1CCOCC1 | null | null | COC(=O)c1cc(COc2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c(C)o1.COc1ccccc1Br>O1CCOCC1>COC(=O)c1cc(COc2ccc(-c3ccccc3OC)cc2)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-32c077bc389d4444b4569049d81dd19a | COC(=O)c1cc(COc2ccc(-c3ccccc3OC)cc2)c(C)o1>>COc1ccccc1-c1ccc(OCc2cc(C(=O)O)oc2C)cc1 | COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)C1=C(C=CC=C1)OC)C>>COC1=C(C=CC=C1)C1=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)O | C[O:20][C:18]([c:17]1[cH:16][c:15]([CH2:14][O:13][c:12]2[cH:11][cH:10][c:9](-[c:8]3[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]3)[cH:25][cH:24]2)[c:22]([CH3:23])[o:21]1)=[O:19]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[c:9]1[cH:10][cH:11][c:12]([O:13][CH2:14][c:15]2[cH:16][c:17]([C:18](=[O:19])[OH:20])[o:21][c:... | COC(=O)c1cc(COc2ccc(-c3ccccc3OC)cc2)c(C)o1 | COc1ccccc1-c1ccc(OCc2cc(C(=O)O)oc2C)cc1 | null | null | O1CCCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ccc(OCc3ccoc3)cc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#8;a:5]>>[#8;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 77.9 | [{"value": 77.9, "product": "COC1=C(C=CC=C1)C1=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A solution of 4-(2′-methoxy-biphenyl-4-yloxymethyl)-5-methyl-furan-2-carboxylic acid methyl ester (125) (40 mg, 0.11 mmoles) in dry tetrahydrofuran (25 ml) was treated with potassium trimethylsilanoate (73 mg, 0.56 mmoles) and the mixture stirred under an argon atmosphere for 16 h. After evaporation of the solvent the ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccoc1 | Other | O1CCCC1 | null | 16 | COC(=O)c1cc(COc2ccc(-c3ccccc3OC)cc2)c(C)o1>O1CCCC1>COc1ccccc1-c1ccc(OCc2cc(C(=O)O)oc2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8a13edad80be449c95a88f481f6b85d9 | COC(=O)c1cc(COc2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c(C)o1.FC(F)Oc1ccc(I)cc1>>COC(=O)c1cc(COc2ccc(-c3ccc(OC(F)F)cc3)cc2)c(C)o1 | COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)B1OC(C(O1)(C)C)(C)C)C.FC(OC1=CC=C(C=C1)I)F.C([O-])([O-])=O.[Cs+].[Cs+].ClCCl.FC(OC1=CC=C(C=C1)I)F.ClCCl>>COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)C1=CC=C(C=C1)OC(F)F)C | CC1(C)OB([c:13]2[cH:12][cH:11][c:10]([O:9][CH2:8][c:7]3[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[o:28][c:26]3[CH3:27])[cH:25][cH:24]2)OC1(C)C.I[c:14]1[cH:15][cH:16][c:17]([O:18][CH:19]([F:20])[F:21])[cH:22][cH:23]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][O:9][c:10]2[cH:11][cH:12][c:13](-[c:14]3[cH:15][cH:16][c... | COC(=O)c1cc(COc2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c(C)o1.FC(F)Oc1ccc(I)cc1 | COC(=O)c1cc(COc2ccc(-c3ccc(OC(F)F)cc3)cc2)c(C)o1 | null | null | O1CCOCC1 | C-C Coupling | Suzuki coupling with boronic esters | 8b44d63590c7228953eb9acb565338c9584155fdcec14c37f9f3f344e065dc2d | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | c1ccc(-c2ccc(OCc3ccoc3)cc2)cc1 | C-C1(-C)-O-B(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-O-C-1(-C)-C.I-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 57.2 | [{"value": 57.2, "product": "COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)C1=CC=C(C=C1)OC(F)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 4 | HOUR | A degassed mixture of 5-methyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxymethyl]-furan-2-carboxylic acid methyl ester (119) (200 mg, 0.54 mmoles), 4-difluoromethoxy-1-iodo-benzene (175 mg, 0.65 mmoles), 2M aqueous cesium carbonate (0.81 ml) and), [1,1′-bis(diphenylphosphino) ferrocene]dichloropalladium... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | B1OCCO1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccoc1.c1ccccc1.c1ccccc1 | HI.B | O1CCOCC1 | 80 | 4 | COC(=O)c1cc(COc2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c(C)o1.FC(F)Oc1ccc(I)cc1>O1CCOCC1>COC(=O)c1cc(COc2ccc(-c3ccc(OC(F)F)cc3)cc2)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5a847f4c405547528e5dae171d2c92c6 | Brc1ncccn1.COC(=O)c1cc(COc2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c(C)o1>>COC(=O)c1cc(COc2ccc(-c3ncccn3)cc2)c(C)o1 | COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)B1OC(C(O1)(C)C)(C)C)C.BrC1=NC=CC=N1>>COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)C1=NC=CC=N1)C | Br[c:14]1[n:15][cH:16][cH:17][cH:18][n:19]1.CC1(C)OB([c:13]2[cH:12][cH:11][c:10]([O:9][CH2:8][c:7]3[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[o:24][c:22]3[CH3:23])[cH:21][cH:20]2)OC1(C)C>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][O:9][c:10]2[cH:11][cH:12][c:13](-[c:14]3[n:15][cH:16][cH:17][cH:18][n:19]3)[cH:20][cH... | Brc1ncccn1.COC(=O)c1cc(COc2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c(C)o1 | COC(=O)c1cc(COc2ccc(-c3ncccn3)cc2)c(C)o1 | null | null | null | C-C Coupling | Suzuki coupling with boronic esters | 90181dd6ff486545b377979be4eda7b1ee93a9a36374e4157c8be739bec9f2e6 | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | c1cnc(-c2ccc(OCc3ccoc3)cc2)nc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].C-C1(-C)-O-B(-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10])-O-C-1(-C)-C>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9]:[c:10] | null | [] | null | null | null | null | Compound (136) was prepared from compound (119) and 2-bromo-pyrimidine by adapting the procedure of Example 30(a). LC/MS System A; Rt=3.43 mins, m/z (ES+)=325 (M+H for C18H16N2O4).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | c1cncnc1.B1OCCO1.c1ccccc1 | c1ccccc1.c1cncnc1 | c1ccoc1.c1ccccc1.c1cncnc1 | HBr.B | null | null | null | Brc1ncccn1.COC(=O)c1cc(COc2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c(C)o1>>COC(=O)c1cc(COc2ccc(-c3ncccn3)cc2)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-79af233fa6814a859a89fefa6149c7f3 | COC(=O)c1cc(COc2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c(C)o1.COc1ccc(Br)c(OC)c1>>COC(=O)c1cc(COc2ccc(-c3ccc(OC)cc3OC)cc2)c(C)o1 | COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)B1OC(C(O1)(C)C)(C)C)C.BrC1=C(C=C(C=C1)OC)OC>>COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)C1=C(C=C(C=C1)OC)OC)C | CC1(C)OB([c:13]2[cH:12][cH:11][c:10]([O:9][CH2:8][c:7]3[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[o:28][c:26]3[CH3:27])[cH:25][cH:24]2)OC1(C)C.Br[c:14]1[cH:15][cH:16][c:17]([O:18][CH3:19])[cH:20][c:21]1[O:22][CH3:23]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][O:9][c:10]2[cH:11][cH:12][c:13](-[c:14]3[cH:15][cH:16][... | COC(=O)c1cc(COc2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c(C)o1.COc1ccc(Br)c(OC)c1 | COC(=O)c1cc(COc2ccc(-c3ccc(OC)cc3OC)cc2)c(C)o1 | null | null | null | C-C Coupling | Suzuki coupling with boronic esters | 8b44d63590c7228953eb9acb565338c9584155fdcec14c37f9f3f344e065dc2d | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | c1ccc(-c2ccc(OCc3ccoc3)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#8:5]):[c:6].C-C1(-C)-O-B(-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11])-O-C-1(-C)-C>>[#8:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]):[c:2]:[c:3] | null | [] | null | null | null | null | Compound (139) was prepared from compound (119) and 1-bromo-2,4-dimethoxy-benzene by adapting the procedure of Example 31(a). LC/MS System A; Rt=4.09 mins.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | B1OCCO1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccoc1.c1ccccc1.c1ccccc1 | HBr.B | null | null | null | COC(=O)c1cc(COc2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c(C)o1.COc1ccc(Br)c(OC)c1>>COC(=O)c1cc(COc2ccc(-c3ccc(OC)cc3OC)cc2)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b22e48cec180493eb8ca108d7f33a7e3 | COc1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)c(OC)c1.NS(=O)(=O)c1ccccc1>>COc1ccc(-c2ccc(OCc3cc(C(=O)NS(=O)(=O)c4ccccc4)oc3C)cc2)c(OC)c1 | COC1=C(C=CC(=C1)OC)C1=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)O.C1(=CC=CC=C1)S(=O)(=O)N.Cl.CN(CCCN=C=NCC)C>>COC1=C(C=CC(=C1)OC)C1=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)NS(=O)(=O)C1=CC=CC=C1 | O[C:16]([c:15]1[cH:14][c:13]([CH2:12][O:11][c:10]2[cH:9][cH:8][c:7](-[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:36][c:33]3[O:34][CH3:35])[cH:32][cH:31]2)[c:29]([CH3:30])[o:28]1)=[O:17].[NH2:18][S:19](=[O:20])(=[O:21])[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10... | COc1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)c(OC)c1.NS(=O)(=O)c1ccccc1 | COc1ccc(-c2ccc(OCc3cc(C(=O)NS(=O)(=O)c4ccccc4)oc3C)cc2)c(OC)c1 | null | CN(C)C1=CC=NC=C1 | O1CCCC1.C(C)#N | Acylation | Carboxylic acid with primary amine to amide | 195a412a8235704efe2985cdc18467ba661e632bab7b61944399ecc813e32a09 | 5e4665bad9c6f58dddd98c5f95e436c640b4c0118b04efea5cd58c7d1755401d | O=C(NS(=O)(=O)c1ccccc1)c1cc(COc2ccc(-c3ccccc3)cc2)co1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[NH2;D1;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[c:3](:[c:4]):[#8;a:5]:[c:6] | 34.8 | [{"value": 34.8, "product": "COC1=C(C=CC(=C1)OC)C1=CC=C(C=C1)OCC=1C=C(OC1C)C(=O)NS(=O)(=O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A stirred solution of 4-(2′,4′-dimethoxy-biphenyl-4-yloxymethyl)-5-methyl-furan-2-carboxylic acid (140) (50 mg, 0.136 mmoles), benzenesulphonamide (32 mg, 0.204 mmoles) and 4-(N,N-dimethylamino)-pyridine (5 mg) in a mixture of tetrahydrofuran (8 ml) and acetonitrile (2 ml) was treated with 1-(3-dimethylaminopropyl)-3-e... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Carboxylic acid | Sulfonamide.Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccoc1.c1ccccc1 | HO- | CN(C)C1=CC=NC=C1.O1CCCC1.C(C)#N | null | 16 | COc1ccc(-c2ccc(OCc3cc(C(=O)O)oc3C)cc2)c(OC)c1.NS(=O)(=O)c1ccccc1>CN(C)C1=CC=NC=C1.O1CCCC1.C(C)#N>COc1ccc(-c2ccc(OCc3cc(C(=O)NS(=O)(=O)c4ccccc4)oc3C)cc2)c(OC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-419665407b5e432f9d2e271fb35c29c6 | COC(=O)c1cc(COc2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c(C)o1.COc1ccc(Br)c(C)c1>>COC(=O)c1cc(COc2ccc(-c3ccc(OC)cc3C)cc2)c(C)o1 | COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)B1OC(C(O1)(C)C)(C)C)C.BrC1=C(C=C(C=C1)OC)C>>COC(=O)C=1OC(=C(C1)COC1=CC=C(C=C1)C1=C(C=C(C=C1)OC)C)C | CC1(C)OB([c:13]2[cH:12][cH:11][c:10]([O:9][CH2:8][c:7]3[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[o:27][c:25]3[CH3:26])[cH:24][cH:23]2)OC1(C)C.Br[c:14]1[cH:15][cH:16][c:17]([O:18][CH3:19])[cH:20][c:21]1[CH3:22]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][O:9][c:10]2[cH:11][cH:12][c:13](-[c:14]3[cH:15][cH:16][c:17](... | COC(=O)c1cc(COc2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c(C)o1.COc1ccc(Br)c(C)c1 | COC(=O)c1cc(COc2ccc(-c3ccc(OC)cc3C)cc2)c(C)o1 | null | null | null | C-C Coupling | Suzuki coupling with boronic esters | 8b44d63590c7228953eb9acb565338c9584155fdcec14c37f9f3f344e065dc2d | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | c1ccc(-c2ccc(OCc3ccoc3)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6].C-C1(-C)-O-B(-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11])-O-C-1(-C)-C>>[C;D1;H3:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]):[c:2]:[c:3] | null | [] | null | null | null | null | Compound (143) was prepared from compound (119) and 1-bromo-4-methoxy-2-methyl-benzene by adapting the procedure of Example 31(a). LC/MS System A; Rt=4.24 mins.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | B1OCCO1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccoc1.c1ccccc1.c1ccccc1 | HBr.B | null | null | null | COC(=O)c1cc(COc2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c(C)o1.COc1ccc(Br)c(C)c1>>COC(=O)c1cc(COc2ccc(-c3ccc(OC)cc3C)cc2)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-27f5cc3427694e1da2beab85727cff68 | Cc1oc(C#N)cc1CO.Oc1ccc(-c2ccccc2)cc1>>Cc1oc(C#N)cc1COc1ccc(-c2ccccc2)cc1 | CC(C)OC(=O)/N=N/C(=O)OC(C)C.OCC=1C=C(OC1C)C#N.C1(=CC=C(C=C1)O)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C1(=CC=C(C=C1)OCC=1C=C(OC1C)C#N)C1=CC=CC=C1 | [CH3:1][c:2]1[o:3][c:4]([C:5]#[N:6])[cH:7][c:8]1[CH2:9][OH:10].O[c:11]1[cH:12][cH:13][c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21][cH:22]1>>[CH3:1][c:2]1[o:3][c:4]([C:5]#[N:6])[cH:7][c:8]1[CH2:9][O:10][c:11]1[cH:12][cH:13][c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21][cH:22]1 | Cc1oc(C#N)cc1CO.Oc1ccc(-c2ccccc2)cc1 | Cc1oc(C#N)cc1COc1ccc(-c2ccccc2)cc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 8915084acbaaf997bf0f89ff5187cb2f89c25dc683fffc57b3391298c8430dd9 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(-c2ccc(OCc3ccoc3)cc2)cc1 | O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8;a:6]:[c:7]:[c:8]-[C:9]-[OH;D1;+0:10]>>[#8;a:6]:[c:7]:[c:8]-[C:9]-[O;H0;D2;+0:10]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 79.2 | [{"value": 79.2, "product": "C1(=CC=C(C=C1)OCC=1C=C(OC1C)C#N)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 5 | MINUTE | Diisopropylazodicarboxylate (1.84 g, 10.6 mmoles) was added to a solution of 4-hydroxymethyl-5-methyl-furan-2-carbonitrile (147) (1.32 g, 9.6 mmoles), biphenyl-4-ol (1.63 g, 9.6 mmoles) and triphenylphosphine (4.3 g, 16.35 mmoles) in tetrahydrofuran (50 mL) with stirring and cooling to 0° C. under an argon atmosphere. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccoc1.c1ccccc1.c1ccccc1 | HO- | O1CCCC1 | 0 | 0.083333 | Cc1oc(C#N)cc1CO.Oc1ccc(-c2ccccc2)cc1>O1CCCC1>Cc1oc(C#N)cc1COc1ccc(-c2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b8900bbc90f4450c81aefb0fb7deb8e5 | Cc1oc(C#N)cc1COc1ccc(-c2ccccc2)cc1.[N-]=[N+]=[N-]>>Cc1oc(-c2nnn[nH]2)cc1COc1ccc(-c2ccccc2)cc1 | C1(=CC=C(C=C1)OCC=1C=C(OC1C)C#N)C1=CC=CC=C1.[N-]=[N+]=[N-].[Na+].C([O-])([O-])=O.[K+].[K+]>>C1(=CC=C(C=C1)OCC=1C=C(OC1C)C1=NN=NN1)C1=CC=CC=C1 | [CH3:1][c:2]1[o:3][c:4]([C:5]#[N:6])[cH:10][c:11]1[CH2:12][O:13][c:14]1[cH:15][cH:16][c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[cH:24][cH:25]1.[N+:7](=[N-:8])=[N-:9]>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[n:6][n:7][n:8][nH:9]2)[cH:10][c:11]1[CH2:12][O:13][c:14]1[cH:15][cH:16][c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:... | Cc1oc(C#N)cc1COc1ccc(-c2ccccc2)cc1.[N-]=[N+]=[N-] | Cc1oc(-c2nnn[nH]2)cc1COc1ccc(-c2ccccc2)cc1 | null | null | CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | 237b84aaa459abf427f233dc6a07a1d9de824f980714e458423189bb68f60f12 | d8c808528b7ee68720aaeebd35cb6a2a30e344748d0066102cdae99843b93cf0 | c1ccc(-c2ccc(OCc3coc(-c4nnn[nH]4)c3)cc2)cc1 | [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]1:[#8;a:7]:[c:8]:[c:9]:[c:10]:1>>[#8;a:7]1:[c:8]:[c:9]:[c:10]:[c;H0;D3;+0:6]:1-[c;H0;D3;+0:5]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:2]:[n;H0;D2;+0:1]:[nH;D2;+0:3]:1 | 55 | [{"value": 55.0, "product": "C1(=CC=C(C=C1)OCC=1C=C(OC1C)C1=NN=NN1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 24 | HOUR | A mixture of 4-(biphenyl-4-yloxymethyl)-5-methyl-furan-2-carbonitrile (148) (100 mg, 0.35 mmoles), sodium azide (27 mg, 0.415 mmoles) and potassium carbonate (62 mg, 0.45 mmoles) in dimethylformamide (5 ml) was heated at 90° C. for 96 hours then at 120° C. for 24 hours. The mixture was evaporated and the residue purifi... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | null | null | c1nnn[nH]1 | c1ccoc1.c1nnn[nH]1.c1ccccc1.c1ccccc1 | null | CN(C=O)C | 90 | 24 | Cc1oc(C#N)cc1COc1ccc(-c2ccccc2)cc1.[N-]=[N+]=[N-]>CN(C=O)C>Cc1oc(-c2nnn[nH]2)cc1COc1ccc(-c2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fb1d3ffecd354896b31b0d389b91a1c5 | COC(=O)c1cc(CO)c(C)o1.Sc1ccc(Br)cc1>>COC(=O)c1cc(CSc2ccc(Br)cc2)c(C)o1 | CC(C)OC(=O)/N=N/C(=O)OC(C)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.COC(=O)C=1OC(=C(C1)CO)C.BrC1=CC=C(C=C1)S>>COC(=O)C=1OC(=C(C1)CSC1=CC=C(C=C1)Br)C | O[CH2:8][c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[o:19][c:17]1[CH3:18].[SH:9][c:10]1[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][S:9][c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]2)[c:17]([CH3:18])[o:19]1 | COC(=O)c1cc(CO)c(C)o1.Sc1ccc(Br)cc1 | COC(=O)c1cc(CSc2ccc(Br)cc2)c(C)o1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | S-alkylation of thiols with alcohols | c119424abb7b621e5fb126e8156c5e4310815e8f2d609f48f2eb427b327d29ac | c1ccf05c97341d9cf75acae4c03f7d5a8212340a35905af6c8d60b4ccc775d1f | c1ccc(SCc2ccoc2)cc1 | O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4](-[C:5](-[#8:6])=[O;D1;H0:7]):[#8;a:8]:[c:9]:1-[C;D1;H3:10].[SH;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]1:[#8;a:8]:[c:9](-[C;D1;H3:10]):[c:2](-[CH2;D2;+0:1]-[S;H0;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:3]:1 | null | [] | null | null | null | null | Diisopropylazodicarboxylate (1.27 g, 6.3 mmoles) was added to a solution of triphenylphosphine (1.65 g, 6.3 mmoles) in tetrahydrofuran (15 ml) with stirring and cooling in an ice/water bath. A solution of 4-hydroxymethyl-5-methyl-furan-2-carboxylic acid methyl ester (16) (536 mg, 3.15 mmoles) and 4-bromo-thiophenol (58... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic thiol | Monosulfide | null | null | c1ccoc1.c1ccccc1 | HO- | O1CCCC1 | null | null | COC(=O)c1cc(CO)c(C)o1.Sc1ccc(Br)cc1>O1CCCC1>COC(=O)c1cc(CSc2ccc(Br)cc2)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-08dae77882a24fb899fc4358c13c2176 | CC1(C)OBOC1(C)C.COC(=O)c1cc(CSc2ccc(Br)cc2)c(C)o1>>COC(=O)c1cc(CSc2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c(C)o1 | ClCCl.CC1(OBOC1(C)C)C.COC(=O)C=1OC(=C(C1)CSC1=CC=C(C=C1)Br)C>>COC(=O)C=1OC(=C(C1)CSC1=CC=C(C=C1)B1OC(C(O1)(C)C)(C)C)C | [BH:14]1[O:15][C:16]([CH3:17])([CH3:18])[C:19]([CH3:20])([CH3:21])[O:22]1.Br[c:13]1[cH:12][cH:11][c:10]([S:9][CH2:8][c:7]2[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[o:27][c:25]2[CH3:26])[cH:24][cH:23]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][S:9][c:10]2[cH:11][cH:12][c:13]([B:14]3[O:15][C:16]([CH3:17])([CH3:18]... | CC1(C)OBOC1(C)C.COC(=O)c1cc(CSc2ccc(Br)cc2)c(C)o1 | COC(=O)c1cc(CSc2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c(C)o1 | null | null | O1CCCC1.O1CCOCC1 | Miscellaneous | OtherReaction | ad2870ebdd035b36ca28b76fce8ec2fa1001820252a6151877804f04f83d958c | f1d1202adfbfb63cdbea2fa31eb5766b49914acb653b77a04e8043b460a99de7 | c1cc(CSc2ccc(B3OCCO3)cc2)co1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8:6]1-[BH;D2;+0:7]-[#8:8]-[C:9]-[C:10]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[B;H0;D3;+0:7]1-[#8:6]-[C:10]-[C:9]-[#8:8]-1):[c:4]:[c:5] | null | [] | 100 | CELSIUS | null | null | [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (30 mg) and 4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (2.34 ml of a 1M solution in tetrahydrofuran) were added to a degassed solution of 4-(4-bromo-phenylsulphanylmethyl)-5-methyl-furan-2-carboxylic acid methyl ester (150) (40... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Boronic ester | B1OCCO1.c1ccccc1 | c1ccccc1.[B]1OCCO1 | c1ccoc1.c1ccccc1.[B]1OCCO1 | HBr | O1CCCC1.O1CCOCC1 | 100 | null | CC1(C)OBOC1(C)C.COC(=O)c1cc(CSc2ccc(Br)cc2)c(C)o1>O1CCCC1.O1CCOCC1>COC(=O)c1cc(CSc2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8f007f3003364e23bbbf9a999df757cb | COC(=O)c1cc(CSc2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c(C)o1.FC(F)Oc1ccc(I)cc1>>COC(=O)c1cc(CSc2ccc(-c3ccc(OC(F)F)cc3)cc2)c(C)o1 | ClCCl.COC(=O)C=1OC(=C(C1)CSC1=CC=C(C=C1)B1OC(C(O1)(C)C)(C)C)C.FC(OC1=CC=C(C=C1)I)F.C([O-])([O-])=O.[Cs+].[Cs+]>>COC(=O)C=1OC(=C(C1)CSC1=CC=C(C=C1)C1=CC=C(C=C1)OC(F)F)C | CC1(C)OB([c:13]2[cH:12][cH:11][c:10]([S:9][CH2:8][c:7]3[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[o:28][c:26]3[CH3:27])[cH:25][cH:24]2)OC1(C)C.I[c:14]1[cH:15][cH:16][c:17]([O:18][CH:19]([F:20])[F:21])[cH:22][cH:23]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][S:9][c:10]2[cH:11][cH:12][c:13](-[c:14]3[cH:15][cH:16][c... | COC(=O)c1cc(CSc2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c(C)o1.FC(F)Oc1ccc(I)cc1 | COC(=O)c1cc(CSc2ccc(-c3ccc(OC(F)F)cc3)cc2)c(C)o1 | null | null | O1CCOCC1 | C-C Coupling | Suzuki coupling with boronic esters | 8b44d63590c7228953eb9acb565338c9584155fdcec14c37f9f3f344e065dc2d | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | c1ccc(-c2ccc(SCc3ccoc3)cc2)cc1 | C-C1(-C)-O-B(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-O-C-1(-C)-C.I-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 60.4 | [{"value": 60.4, "product": "COC(=O)C=1OC(=C(C1)CSC1=CC=C(C=C1)C1=CC=C(C=C1)OC(F)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | [1,1′-Bis(diphenylphosphino) ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (12.8 mg) was added to a degassed mixture of 5-methyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylsulphanylmethyl]-furan-2-carboxylic acid methyl ester (151) (200 mg, 0.516 mmoles), 1-difluoromethoxy-4-iodo-ben... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | B1OCCO1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccoc1.c1ccccc1.c1ccccc1 | HI.B | O1CCOCC1 | 100 | null | COC(=O)c1cc(CSc2ccc(B3OC(C)(C)C(C)(C)O3)cc2)c(C)o1.FC(F)Oc1ccc(I)cc1>O1CCOCC1>COC(=O)c1cc(CSc2ccc(-c3ccc(OC(F)F)cc3)cc2)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-21b55cf35030424cb7583962d1272e3c | Cc1ccccc1S(N)(=O)=O.Cc1oc(C(=O)O)cc1CSc1ccc(-c2ccc(OC(F)F)cc2)cc1>>Cc1ccccc1S(=O)(=O)NC(=O)c1cc(CSc2ccc(-c3ccc(OC(F)F)cc3)cc2)c(C)o1 | FC(OC1=CC=C(C=C1)C1=CC=C(C=C1)SCC=1C=C(OC1C)C(=O)O)F.CC1=C(C=CC=C1)S(=O)(=O)N>>FC(OC1=CC=C(C=C1)C1=CC=C(C=C1)SCC=1C=C(OC1C)C(=O)NS(=O)(=O)C1=C(C=CC=C1)C)F | [CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[S:8](=[O:9])(=[O:10])[NH2:11].O[C:12](=[O:13])[c:14]1[cH:15][c:16]([CH2:17][S:18][c:19]2[cH:20][cH:21][c:22](-[c:23]3[cH:24][cH:25][c:26]([O:27][CH:28]([F:29])[F:30])[cH:31][cH:32]3)[cH:33][cH:34]2)[c:35]([CH3:36])[o:37]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[S:8](=[O:... | Cc1ccccc1S(N)(=O)=O.Cc1oc(C(=O)O)cc1CSc1ccc(-c2ccc(OC(F)F)cc2)cc1 | Cc1ccccc1S(=O)(=O)NC(=O)c1cc(CSc2ccc(-c3ccc(OC(F)F)cc3)cc2)c(C)o1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 195a412a8235704efe2985cdc18467ba661e632bab7b61944399ecc813e32a09 | 5e4665bad9c6f58dddd98c5f95e436c640b4c0118b04efea5cd58c7d1755401d | O=C(NS(=O)(=O)c1ccccc1)c1cc(CSc2ccc(-c3ccccc3)cc2)co1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[NH2;D1;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11]>>[O;D1;H0:9]=[#16:8](=[O;D1;H0:10])(-[c:11])-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6] | null | [] | null | null | null | null | Compound (154) was prepared from compound (153) and 2-methyl-benzenesulphonamide by adapting the procedure of Example 34(c). LC/MS System D; Rt=11.61 mins, m/z (ES+)=544 (M+H for C27H23F2NO5S2).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Carboxylic acid | Sulfonamide.Secondary amide | null | null | c1ccccc1.c1ccoc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | Cc1ccccc1S(N)(=O)=O.Cc1oc(C(=O)O)cc1CSc1ccc(-c2ccc(OC(F)F)cc2)cc1>>Cc1ccccc1S(=O)(=O)NC(=O)c1cc(CSc2ccc(-c3ccc(OC(F)F)cc3)cc2)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-546f1a850b5743a5a9dda2d130876e8d | COC(=O)c1cc(CO)c(C)o1>>COC(=O)c1cc(C=O)c(C)o1 | O.O.O.O.O.S(=S)(=O)([O-])[O-].[Na+].[Na+].C(C)(=O)OI1(OC(C2=CC=CC=C12)=O)(OC(C)=O)OC(C)=O.COC(=O)C=1OC(=C(C1)CO)C.C([O-])(O)=O.[Na+]>>COC(=O)C=1OC(=C(C1)C=O)C | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][OH:9])[c:10]([CH3:11])[o:12]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]=[O:9])[c:10]([CH3:11])[o:12]1 | COC(=O)c1cc(CO)c(C)o1 | COC(=O)c1cc(C=O)c(C)o1 | null | null | ClCCl.C(C)OCC | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccoc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[#8;a:5]:[c:6](-[C;D1;H3:7]):[c:8](-[CH2;D2;+0:9]-[OH;D1;+0:10]):[c:11]:1>>[#8:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[#8;a:5]:[c:6](-[C;D1;H3:7]):[c:8](-[CH;D2;+0:9]=[O;H0;D1;+0:10]):[c:11]:1 | 70.8 | [{"value": 70.8, "product": "COC(=O)C=1OC(=C(C1)C=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 20 | MINUTE | Acetic acid 1,1-diacetoxy-3-oxo-1λ5-ioda-2-oxa-indan-1-yl ester (Dess-Martin reagent) (549 mg, 1.293 mmoles) in dry dichloromethane was added to a solution of 4-hydroxymethyl-5-methyl-furan-2-carboxylic acid methyl ester (16) (200 mg, 1.176 mmoles) in dry dichloromethane (9 ml) with cooling to 0° C. under an argon atmo... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccoc1 | null | ClCCl.C(C)OCC | 0 | 0.333333 | COC(=O)c1cc(CO)c(C)o1>ClCCl.C(C)OCC>COC(=O)c1cc(C=O)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-42862eee63924cddb9006d6a9ab1e024 | COC(=O)c1cc(C=O)c(C)o1.Nc1ccc(-c2ccccc2)cc1>>COC(=O)c1cc(CNc2ccc(-c3ccccc3)cc2)c(C)o1 | C1(=CC=C(C=C1)N)C1=CC=CC=C1.COC(=O)C=1OC(=C(C1)C=O)C.C(#N)[BH3-].[Na+]>>COC(=O)C=1OC(=C(C1)CNC1=CC=C(C=C1)C1=CC=CC=C1)C | O=[CH:8][c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[o:24][c:22]1[CH3:23].[NH2:9][c:10]1[cH:11][cH:12][c:13](-[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:20][cH:21]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][NH:9][c:10]2[cH:11][cH:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[cH:20][cH:21]2)[c:2... | COC(=O)c1cc(C=O)c(C)o1.Nc1ccc(-c2ccccc2)cc1 | COC(=O)c1cc(CNc2ccc(-c3ccccc3)cc2)c(C)o1 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(-c2ccc(NCc3ccoc3)cc2)cc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[c:4](-[C:5](-[#8:6])=[O;D1;H0:7]):[#8;a:8]:[c:9]:1-[C;D1;H3:10].[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]1:[#8;a:8]:[c:9](-[C;D1;H3:10]):[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:3]:1 | 29.1 | [{"value": 29.1, "product": "COC(=O)C=1OC(=C(C1)CNC1=CC=C(C=C1)C1=CC=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A solution of biphenyl-4-ylamine (150 mg, 0.883 mmoles) and 4-formyl-5-methyl-furan-2-carboxylic acid methyl ester (157) (135 mg, 0.803 mmoles) in methanol (2.0 ml) was stirred over molecular sieves (type 3 Å) for 1 hour. Sodium cyanoborohydride (55 mg, 0.883 mmoles) was added and the mixture stirred for 18 hour at roo... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccoc1.c1ccccc1.c1ccccc1 | Other | CO | null | 18 | COC(=O)c1cc(C=O)c(C)o1.Nc1ccc(-c2ccccc2)cc1>CO>COC(=O)c1cc(CNc2ccc(-c3ccccc3)cc2)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e646003c904d4701a39f4a2a6e5f1e6f | COC(=O)c1cc(CO)c(C)o1.Cc1ccc(S(=O)(=O)Cl)cc1>>COC(=O)c1cc(CCl)c(C)o1 | C(C)N(CC)CC.CC1=CC=C(C=C1)S(=O)(=O)Cl.COC(=O)C=1OC(=C(C1)CO)C>>COC(=O)C=1OC(=C(C1)CCl)C | O[CH2:8][c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[o:12][c:10]1[CH3:11].Cc1ccc(S(=O)(=O)[Cl:9])cc1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][Cl:9])[c:10]([CH3:11])[o:12]1 | COC(=O)c1cc(CO)c(C)o1.Cc1ccc(S(=O)(=O)Cl)cc1 | COC(=O)c1cc(CCl)c(C)o1 | null | null | ClCCl | Functional Group Interconversion | Alcohol to chloride_sulfonyl chloride | 46eb49b1f728a0d336f2089cc941f1be7b941b4ddaef68327099a4e18f4b1c02 | ebb4f73ae894ea29d308da9353b73dcd2a829947c5cd449c678fae1fc55ddffd | c1ccoc1 | C-c1:c:c:c(-S(=O)(=O)-[Cl;H0;D1;+0:1]):c:c:1.O-[CH2;D2;+0:2]-[c:3]1:[c:4]:[c:5](-[C:6](-[#8:7])=[O;D1;H0:8]):[#8;a:9]:[c:10]:1-[C;D1;H3:11]>>[#8:7]-[C:6](=[O;D1;H0:8])-[c:5]1:[#8;a:9]:[c:10](-[C;D1;H3:11]):[c:3](-[CH2;D2;+0:2]-[Cl;H0;D1;+0:1]):[c:4]:1 | 33.8 | [{"value": 33.8, "product": "COC(=O)C=1OC(=C(C1)CCl)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | Triethylamine (196 μl, 1.41 mmoles), followed by 4-methyl-benzenesulphonyl chloride (247 mg, 1.293 mmoles) were added to a stirred solution of 4-hydroxymethyl-5-methyl-furan-2-carboxylic acid methyl ester (16) (200 mg, 1.176 mmoles) in dry dichloromethane at 0° C. under an argon atmosphere. The reaction mixture was sti... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary alcohol.Sulfonyl halide | Primary halide | c1ccccc1 | null | c1ccoc1 | TsOH.HO- | ClCCl | 0 | 0.25 | COC(=O)c1cc(CO)c(C)o1.Cc1ccc(S(=O)(=O)Cl)cc1>ClCCl>COC(=O)c1cc(CCl)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-80ca010d9cf343f0a90c04484c6401ac | COC(=O)c1cc(CCl)c(C)o1.Nc1ccc(-c2ccccc2)cc1>>COC(=O)c1cc(CNc2ccc(-c3ccccc3)cc2)c(C)o1 | [I-].[K+].C1(=CC=C(C=C1)N)C1=CC=CC=C1.COC(=O)C=1OC(=C(C1)CCl)C.C([O-])([O-])=O.[K+].[K+]>>COC(=O)C=1OC(=C(C1)CNC1=CC=C(C=C1)C1=CC=CC=C1)C | Cl[CH2:8][c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[o:24][c:22]1[CH3:23].[NH2:9][c:10]1[cH:11][cH:12][c:13](-[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:20][cH:21]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][NH:9][c:10]2[cH:11][cH:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[cH:20][cH:21]2)[c:... | COC(=O)c1cc(CCl)c(C)o1.Nc1ccc(-c2ccccc2)cc1 | COC(=O)c1cc(CNc2ccc(-c3ccccc3)cc2)c(C)o1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(-c2ccc(NCc3ccoc3)cc2)cc1 | Cl-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4](-[C:5](-[#8:6])=[O;D1;H0:7]):[#8;a:8]:[c:9]:1-[C;D1;H3:10].[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]1:[#8;a:8]:[c:9](-[C;D1;H3:10]):[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:3]:1 | 71.1 | [{"value": 71.1, "product": "COC(=O)C=1OC(=C(C1)CNC1=CC=C(C=C1)C1=CC=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Potassium iodide (32 mg) and a solution of biphenyl-4-ylamine (74 mg, 0.438 mmoles) in tetrahydrofuran (1 ml) was added to a mixture of 4-chloromethyl-5-methyl-furan-2-carboxylic acid methyl ester (159) (75 mg, 0.398 mmoles) and potassium carbonate (83 mg) in tetrahydrofuran (1 ml). The mixture was stirred at room temp... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccoc1.c1ccccc1.c1ccccc1 | HCl | O1CCCC1 | null | 16 | COC(=O)c1cc(CCl)c(C)o1.Nc1ccc(-c2ccccc2)cc1>O1CCCC1>COC(=O)c1cc(CNc2ccc(-c3ccccc3)cc2)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ab09486afca74d20a134ba0fe5071a3c | COC(=O)c1cc(CNc2ccc(-c3ccccc3)cc2)c(C)o1>>Cc1oc(C(=O)O)cc1CNc1ccc(-c2ccccc2)cc1 | COC(=O)C=1OC(=C(C1)CNC1=CC=C(C=C1)C1=CC=CC=C1)C>>C1(=CC=C(C=C1)NCC=1C=C(OC1C)C(=O)O)C1=CC=CC=C1 | C[O:7][C:5]([c:4]1[o:3][c:2]([CH3:1])[c:9]([CH2:10][NH:11][c:12]2[cH:13][cH:14][c:15](-[c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[cH:22][cH:23]2)[cH:8]1)=[O:6]>>[CH3:1][c:2]1[o:3][c:4]([C:5](=[O:6])[OH:7])[cH:8][c:9]1[CH2:10][NH:11][c:12]1[cH:13][cH:14][c:15](-[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[cH:22][cH:23... | COC(=O)c1cc(CNc2ccc(-c3ccccc3)cc2)c(C)o1 | Cc1oc(C(=O)O)cc1CNc1ccc(-c2ccccc2)cc1 | null | null | O1CCCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ccc(NCc3ccoc3)cc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#8;a:5]>>[#8;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 40.2 | [{"value": 40.2, "product": "C1(=CC=C(C=C1)NCC=1C=C(OC1C)C(=O)O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A solution of 4-(biphenyl-4-ylaminomethyl)-5-methyl-furan-2-carboxylic acid methyl ester (158) (91 mg, 0.283 mmoles) in dry tetrahydrofuran (5 ml) was treated with potassium trimethylsilanoate (182 mg, 1.42 mmoles) and the mixture stirred under an argon atmosphere for 3 hours. After evaporation of the solvent, the resi... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccoc1.c1ccccc1.c1ccccc1 | Other | O1CCCC1 | null | 3 | COC(=O)c1cc(CNc2ccc(-c3ccccc3)cc2)c(C)o1>O1CCCC1>Cc1oc(C(=O)O)cc1CNc1ccc(-c2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1cc4c2ff67f945298a1bc699b95b927c | Cc1oc(C(=O)O)cc1CNc1ccc(-c2ccccc2)cc1.NS(=O)(=O)c1ccccc1>>Cc1oc(C(=O)NS(=O)(=O)c2ccccc2)cc1CNc1ccc(-c2ccccc2)cc1 | C1(=CC=C(C=C1)NCC=1C=C(OC1C)C(=O)O)C1=CC=CC=C1.C1(=CC=CC=C1)S(=O)(=O)N.C(C)N(CC)CC.Cl.CN(CCCN=C=NCC)C>>C1(=CC=C(C=C1)NCC=1C=C(OC1C)C(=O)NS(=O)(=O)C1=CC=CC=C1)C1=CC=CC=C1 | O[C:5]([c:4]1[o:3][c:2]([CH3:1])[c:18]([CH2:19][NH:20][c:21]2[cH:22][cH:23][c:24](-[c:25]3[cH:26][cH:27][cH:28][cH:29][cH:30]3)[cH:31][cH:32]2)[cH:17]1)=[O:6].[NH2:7][S:8](=[O:9])(=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][c:2]1[o:3][c:4]([C:5](=[O:6])[NH:7][S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][... | Cc1oc(C(=O)O)cc1CNc1ccc(-c2ccccc2)cc1.NS(=O)(=O)c1ccccc1 | Cc1oc(C(=O)NS(=O)(=O)c2ccccc2)cc1CNc1ccc(-c2ccccc2)cc1 | null | CN(C)C1=CC=NC=C1 | O1CCCC1.C(C)#N | Acylation | Carboxylic acid with primary amine to amide | 195a412a8235704efe2985cdc18467ba661e632bab7b61944399ecc813e32a09 | 5e4665bad9c6f58dddd98c5f95e436c640b4c0118b04efea5cd58c7d1755401d | O=C(NS(=O)(=O)c1ccccc1)c1cc(CNc2ccc(-c3ccccc3)cc2)co1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[NH2;D1;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11]>>[O;D1;H0:9]=[#16:8](=[O;D1;H0:10])(-[c:11])-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6] | 49.8 | [{"value": 49.8, "product": "C1(=CC=C(C=C1)NCC=1C=C(OC1C)C(=O)NS(=O)(=O)C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 19 | HOUR | A stirred solution of 4-(biphenyl-4-ylaminomethyl)-5-methyl-furan-2-carboxylic acid (160) (15 mg, 0.036 mmoles), benzenesulphonamide (17 mg, 0.107 mmoles) and 4-(N,N-dimethylamino)-pyridine (1 mg) in a mixture of tetrahydrofuran (3 ml) and acetonitrile (0.5 ml) was treated with triethylamine (5.5 μl, 0.039 mmoles) and ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Carboxylic acid | Sulfonamide.Secondary amide | null | null | c1ccoc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | CN(C)C1=CC=NC=C1.O1CCCC1.C(C)#N | null | 19 | Cc1oc(C(=O)O)cc1CNc1ccc(-c2ccccc2)cc1.NS(=O)(=O)c1ccccc1>CN(C)C1=CC=NC=C1.O1CCCC1.C(C)#N>Cc1oc(C(=O)NS(=O)(=O)c2ccccc2)cc1CNc1ccc(-c2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d1a83f1c9f9749bfadc7b099ff1d977e | Cc1ccccc1S(N)(=O)=O.Cc1oc(C(=O)O)cc1CNc1ccc(-c2ccccc2)cc1>>Cc1ccccc1S(=O)(=O)NC(=O)c1cc(CNc2ccc(-c3ccccc3)cc2)c(C)o1 | C1(=CC=C(C=C1)NCC=1C=C(OC1C)C(=O)O)C1=CC=CC=C1.CC1=C(C=CC=C1)S(=O)(=O)N>>C1(=CC=C(C=C1)NCC=1C=C(OC1C)C(=O)NS(=O)(=O)C1=C(C=CC=C1)C)C1=CC=CC=C1 | [CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[S:8](=[O:9])(=[O:10])[NH2:11].O[C:12](=[O:13])[c:14]1[cH:15][c:16]([CH2:17][NH:18][c:19]2[cH:20][cH:21][c:22](-[c:23]3[cH:24][cH:25][cH:26][cH:27][cH:28]3)[cH:29][cH:30]2)[c:31]([CH3:32])[o:33]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[S:8](=[O:9])(=[O:10])[NH:11][C:12](=... | Cc1ccccc1S(N)(=O)=O.Cc1oc(C(=O)O)cc1CNc1ccc(-c2ccccc2)cc1 | Cc1ccccc1S(=O)(=O)NC(=O)c1cc(CNc2ccc(-c3ccccc3)cc2)c(C)o1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 195a412a8235704efe2985cdc18467ba661e632bab7b61944399ecc813e32a09 | 5e4665bad9c6f58dddd98c5f95e436c640b4c0118b04efea5cd58c7d1755401d | O=C(NS(=O)(=O)c1ccccc1)c1cc(CNc2ccc(-c3ccccc3)cc2)co1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[NH2;D1;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11]>>[O;D1;H0:9]=[#16:8](=[O;D1;H0:10])(-[c:11])-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6] | null | [] | null | null | null | null | Compound (162) was prepared from compound (160) and 2-methyl-benzenesulphonamide by adapting the procedure of Example 38(f). LC/MS System D; Rt=10.39 mins, m/z (ES+)=461 (M+H for C26H24N2O4S).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Carboxylic acid | Sulfonamide.Secondary amide | null | null | c1ccccc1.c1ccoc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | Cc1ccccc1S(N)(=O)=O.Cc1oc(C(=O)O)cc1CNc1ccc(-c2ccccc2)cc1>>Cc1ccccc1S(=O)(=O)NC(=O)c1cc(CNc2ccc(-c3ccccc3)cc2)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e9597d101bd24d74a58afd7c9a04f7fb | COC(=O)c1cc(CNc2ccc(-c3ccc(OC)cn3)cc2)c(C)o1>>COc1ccc(-c2ccc(NCc3cc(C(=O)O)oc3C)cc2)nc1 | Cl.FC(C(=O)O)(F)F.COC(=O)C=1OC(=C(C1)CNC1=CC=C(C=C1)C1=NC=C(C=C1)OC)C>>Cl.COC=1C=CC(=NC1)C1=CC=C(C=C1)NCC=1C=C(OC1C)C(=O)O | C[O:18][C:16]([c:15]1[cH:14][c:13]([CH2:12][NH:11][c:10]2[cH:9][cH:8][c:7](-[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:25][n:24]3)[cH:23][cH:22]2)[c:20]([CH3:21])[o:19]1)=[O:17]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([NH:11][CH2:12][c:13]3[cH:14][c:15]([C:16](=[O:17])[OH:18])[o:19][c:20]3[CH3:21])... | COC(=O)c1cc(CNc2ccc(-c3ccc(OC)cn3)cc2)c(C)o1 | COc1ccc(-c2ccc(NCc3cc(C(=O)O)oc3C)cc2)nc1 | null | null | O1CCCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ccc(NCc3ccoc3)cc2)nc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#8;a:5]>>[#8;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | 16 | HOUR | A solution of 4-{[4-(5-methoxy-pyridin-2-yl)-phenylamino]-methyl}-5-methyl-furan-2-carboxylic acid methyl ester trifluoroacetic acid salt (165) (38 mg, 0.082 mmoles) in tetrahydrofuran (4 ml) was treated with potassium trimethylsilanoate (63 mg, 0.049 mmoles) and the mixture stirred at room temperature for 16 hours. Th... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1.c1ccccc1.c1ccoc1 | Other | O1CCCC1 | null | 16 | COC(=O)c1cc(CNc2ccc(-c3ccc(OC)cn3)cc2)c(C)o1>O1CCCC1>COc1ccc(-c2ccc(NCc3cc(C(=O)O)oc3C)cc2)nc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d1db7f0365564cd88479d02ef3124c02 | COc1ccc(-c2ccc(NCc3cc(C(=O)O)oc3C)cc2)nc1.Cc1ccccc1S(N)(=O)=O>>COc1ccc(-c2ccc(NCc3cc(C(=O)NS(=O)(=O)c4ccccc4C)oc3C)cc2)nc1 | C(C)N(CC)CC.C=1(C(=CC=CC1)S(=O)(=O)N)C.Cl.CN(CCCN=C=NCC)C.Cl.COC=1C=CC(=NC1)C1=CC=C(C=C1)NCC=1C=C(OC1C)C(=O)O>>COC=1C=CC(=NC1)C1=CC=C(C=C1)NCC=1C=C(OC1C)C(=O)NS(=O)(=O)C1=C(C=CC=C1)C | O[C:16]([c:15]1[cH:14][c:13]([CH2:12][NH:11][c:10]2[cH:9][cH:8][c:7](-[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:35][n:34]3)[cH:33][cH:32]2)[c:30]([CH3:31])[o:29]1)=[O:17].[NH2:18][S:19](=[O:20])(=[O:21])[c:22]1[cH:23][cH:24][cH:25][cH:26][c:27]1[CH3:28]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([NH:... | COc1ccc(-c2ccc(NCc3cc(C(=O)O)oc3C)cc2)nc1.Cc1ccccc1S(N)(=O)=O | COc1ccc(-c2ccc(NCc3cc(C(=O)NS(=O)(=O)c4ccccc4C)oc3C)cc2)nc1 | null | CN(C)C1=CC=NC=C1 | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 195a412a8235704efe2985cdc18467ba661e632bab7b61944399ecc813e32a09 | 5e4665bad9c6f58dddd98c5f95e436c640b4c0118b04efea5cd58c7d1755401d | O=C(NS(=O)(=O)c1ccccc1)c1cc(CNc2ccc(-c3ccccn3)cc2)co1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[NH2;D1;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[c:3](:[c:4]):[#8;a:5]:[c:6] | 2.8 | [{"value": 2.8, "product": "COC=1C=CC(=NC1)C1=CC=C(C=C1)NCC=1C=C(OC1C)C(=O)NS(=O)(=O)C1=C(C=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A suspension of 4-{[4-(5-methoxy-pyridin-2-yl)-phenylamino]-methyl}-5-methyl-furan-2-carboxylic acid hydrochloride salt (166) (30 mg, 0.08 mmoles) in tetrahydrofuran (5 ml) was treated with toluene-2-sulphonamide (41 mg, 0.24 mmoles), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (34 mg, 0.176 mmoles) and... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Carboxylic acid | Sulfonamide.Secondary amide | null | null | c1ccncc1.c1ccccc1.c1ccoc1.c1ccccc1 | HO- | CN(C)C1=CC=NC=C1.O1CCCC1 | null | 16 | COc1ccc(-c2ccc(NCc3cc(C(=O)O)oc3C)cc2)nc1.Cc1ccccc1S(N)(=O)=O>CN(C)C1=CC=NC=C1.O1CCCC1>COc1ccc(-c2ccc(NCc3cc(C(=O)NS(=O)(=O)c4ccccc4C)oc3C)cc2)nc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ccf9008942794e5aa78e6b6850432f5b | COC(=O)c1cc(CCl)c(C)o1.Nc1ccc(-c2ccc(OC(F)F)cc2)cc1>>COC(=O)c1cc(CNc2ccc(-c3ccc(OC(F)F)cc3)cc2)c(C)o1 | COC(=O)C=1OC(=C(C1)CCl)C.FC(OC1=CC=C(C=C1)C1=CC=C(C=C1)N)F>>COC(=O)C=1OC(=C(C1)CNC1=CC=C(C=C1)C1=CC=C(C=C1)OC(F)F)C | Cl[CH2:8][c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[o:28][c:26]1[CH3:27].[NH2:9][c:10]1[cH:11][cH:12][c:13](-[c:14]2[cH:15][cH:16][c:17]([O:18][CH:19]([F:20])[F:21])[cH:22][cH:23]2)[cH:24][cH:25]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][NH:9][c:10]2[cH:11][cH:12][c:13](-[c:14]3[cH:15][cH:16][c:17]([O:18][... | COC(=O)c1cc(CCl)c(C)o1.Nc1ccc(-c2ccc(OC(F)F)cc2)cc1 | COC(=O)c1cc(CNc2ccc(-c3ccc(OC(F)F)cc3)cc2)c(C)o1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(-c2ccc(NCc3ccoc3)cc2)cc1 | Cl-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4](-[C:5](-[#8:6])=[O;D1;H0:7]):[#8;a:8]:[c:9]:1-[C;D1;H3:10].[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]1:[#8;a:8]:[c:9](-[C;D1;H3:10]):[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:3]:1 | null | [] | null | null | null | null | Compound (170) was prepared from compounds (159) and (169) by adapting the procedure of Example 38(d). (420 mg). LC/MS System A; Rt=4.00 mins, m/z (ES+)=388 (M+H) and 429 (M+H acetonitrile adduct) for C21H19F2NO3.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccoc1.c1ccccc1.c1ccccc1 | HCl | C(C)#N | null | null | COC(=O)c1cc(CCl)c(C)o1.Nc1ccc(-c2ccc(OC(F)F)cc2)cc1>C(C)#N>COC(=O)c1cc(CNc2ccc(-c3ccc(OC(F)F)cc3)cc2)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ce63af510995437e92187b6693f28e47 | Cc1oc(C(=O)O)cc1CNc1ccc(-c2ccc(OC(F)F)cc2)cc1.NS(=O)(=O)c1ccccc1>>Cc1oc(C(=O)NS(=O)(=O)c2ccccc2)cc1CNc1ccc(-c2ccc(OC(F)F)cc2)cc1 | FC(OC1=CC=C(C=C1)C1=CC=C(C=C1)NCC=1C=C(OC1C)C(=O)O)F.C1(=CC=CC=C1)S(=O)(=O)N>>FC(OC1=CC=C(C=C1)C1=CC=C(C=C1)NCC=1C=C(OC1C)C(=O)NS(=O)(=O)C1=CC=CC=C1)F | O[C:5]([c:4]1[o:3][c:2]([CH3:1])[c:18]([CH2:19][NH:20][c:21]2[cH:22][cH:23][c:24](-[c:25]3[cH:26][cH:27][c:28]([O:29][CH:30]([F:31])[F:32])[cH:33][cH:34]3)[cH:35][cH:36]2)[cH:17]1)=[O:6].[NH2:7][S:8](=[O:9])(=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][c:2]1[o:3][c:4]([C:5](=[O:6])[NH:7][S:8](=[O:9])(=[... | Cc1oc(C(=O)O)cc1CNc1ccc(-c2ccc(OC(F)F)cc2)cc1.NS(=O)(=O)c1ccccc1 | Cc1oc(C(=O)NS(=O)(=O)c2ccccc2)cc1CNc1ccc(-c2ccc(OC(F)F)cc2)cc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 195a412a8235704efe2985cdc18467ba661e632bab7b61944399ecc813e32a09 | 5e4665bad9c6f58dddd98c5f95e436c640b4c0118b04efea5cd58c7d1755401d | O=C(NS(=O)(=O)c1ccccc1)c1cc(CNc2ccc(-c3ccccc3)cc2)co1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[NH2;D1;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11]>>[O;D1;H0:9]=[#16:8](=[O;D1;H0:10])(-[c:11])-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6] | null | [] | null | null | null | null | Compound (172) was prepared from compound (171) and benzenesulphonamide by adapting the procedure of Example 38(f). LC/MS System D; Rt=10.38 mins, m/z (ES+)=513 (M+H for C26H22F2N2O5S).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Carboxylic acid | Sulfonamide.Secondary amide | null | null | c1ccoc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | Cc1oc(C(=O)O)cc1CNc1ccc(-c2ccc(OC(F)F)cc2)cc1.NS(=O)(=O)c1ccccc1>>Cc1oc(C(=O)NS(=O)(=O)c2ccccc2)cc1CNc1ccc(-c2ccc(OC(F)F)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5258ab6b08134b9dac12a009777659f1 | Cc1ccccc1S(N)(=O)=O.Cc1oc(C(=O)O)cc1CNc1ccc(-c2ccc(OC(F)F)cc2)cc1>>Cc1ccccc1S(=O)(=O)NC(=O)c1cc(CNc2ccc(-c3ccc(OC(F)F)cc3)cc2)c(C)o1 | FC(OC1=CC=C(C=C1)C1=CC=C(C=C1)NCC=1C=C(OC1C)C(=O)O)F.CC1=C(C=CC=C1)S(=O)(=O)N>>FC(OC1=CC=C(C=C1)C1=CC=C(C=C1)NCC=1C=C(OC1C)C(=O)NS(=O)(=O)C1=C(C=CC=C1)C)F | [CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[S:8](=[O:9])(=[O:10])[NH2:11].O[C:12](=[O:13])[c:14]1[cH:15][c:16]([CH2:17][NH:18][c:19]2[cH:20][cH:21][c:22](-[c:23]3[cH:24][cH:25][c:26]([O:27][CH:28]([F:29])[F:30])[cH:31][cH:32]3)[cH:33][cH:34]2)[c:35]([CH3:36])[o:37]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[S:8](=[O... | Cc1ccccc1S(N)(=O)=O.Cc1oc(C(=O)O)cc1CNc1ccc(-c2ccc(OC(F)F)cc2)cc1 | Cc1ccccc1S(=O)(=O)NC(=O)c1cc(CNc2ccc(-c3ccc(OC(F)F)cc3)cc2)c(C)o1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 195a412a8235704efe2985cdc18467ba661e632bab7b61944399ecc813e32a09 | 5e4665bad9c6f58dddd98c5f95e436c640b4c0118b04efea5cd58c7d1755401d | O=C(NS(=O)(=O)c1ccccc1)c1cc(CNc2ccc(-c3ccccc3)cc2)co1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[NH2;D1;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11]>>[O;D1;H0:9]=[#16:8](=[O;D1;H0:10])(-[c:11])-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6] | null | [] | null | null | null | null | Compound (173) was prepared from compound (171) and 2-methyl-benzenesulphonamide by adapting the procedure of Example 38(f). LC/MS System D; Rt=10.63 mins, m/z (ES+)=527 (M+H for C27H24F2N2O5S).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Carboxylic acid | Sulfonamide.Secondary amide | null | null | c1ccccc1.c1ccoc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | Cc1ccccc1S(N)(=O)=O.Cc1oc(C(=O)O)cc1CNc1ccc(-c2ccc(OC(F)F)cc2)cc1>>Cc1ccccc1S(=O)(=O)NC(=O)c1cc(CNc2ccc(-c3ccc(OC(F)F)cc3)cc2)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f252a2fcd224468bbd28488e1f44e8fc | Cc1noc(C)c1S(N)(=O)=O.Cc1oc(C(=O)O)cc1CNc1ccc(-c2ccc(OC(F)F)cc2)cc1>>Cc1noc(C)c1S(=O)(=O)NC(=O)c1cc(CNc2ccc(-c3ccc(OC(F)F)cc3)cc2)c(C)o1 | F[P-](F)(F)(F)(F)F.N1(N=NC2=C1N=CC=C2)OC(=[N+](C)C)N(C)C.C(C)(C)N(CC)C(C)C.FC(OC1=CC=C(C=C1)C1=CC=C(C=C1)NCC=1C=C(OC1C)C(=O)O)F.CC1=NOC(=C1S(=O)(=O)N)C>>FC(OC1=CC=C(C=C1)C1=CC=C(C=C1)NCC=1C=C(OC1C)C(=O)NS(=O)(=O)C=1C(=NOC1C)C)F | [CH3:1][c:2]1[n:3][o:4][c:5]([CH3:6])[c:7]1[S:8](=[O:9])(=[O:10])[NH2:11].O[C:12](=[O:13])[c:14]1[cH:15][c:16]([CH2:17][NH:18][c:19]2[cH:20][cH:21][c:22](-[c:23]3[cH:24][cH:25][c:26]([O:27][CH:28]([F:29])[F:30])[cH:31][cH:32]3)[cH:33][cH:34]2)[c:35]([CH3:36])[o:37]1>>[CH3:1][c:2]1[n:3][o:4][c:5]([CH3:6])[c:7]1[S:8](=[O... | Cc1noc(C)c1S(N)(=O)=O.Cc1oc(C(=O)O)cc1CNc1ccc(-c2ccc(OC(F)F)cc2)cc1 | Cc1noc(C)c1S(=O)(=O)NC(=O)c1cc(CNc2ccc(-c3ccc(OC(F)F)cc3)cc2)c(C)o1 | null | null | CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 195a412a8235704efe2985cdc18467ba661e632bab7b61944399ecc813e32a09 | 5e4665bad9c6f58dddd98c5f95e436c640b4c0118b04efea5cd58c7d1755401d | O=C(NS(=O)(=O)c1cnoc1)c1cc(CNc2ccc(-c3ccccc3)cc2)co1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[NH2;D1;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11]1:[c:12]:[#7;a:13]:[#8;a:14]:[c:15]:1>>[O;D1;H0:9]=[#16:8](=[O;D1;H0:10])(-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6])-[c:11]1:[c:12]:[#7;a:13]:[#8;a:14]:[c:15]:1 | 3.7 | [{"value": 3.7, "product": "FC(OC1=CC=C(C=C1)C1=CC=C(C=C1)NCC=1C=C(OC1C)C(=O)NS(=O)(=O)C=1C(=NOC1C)C)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Diisopropylethylamine (60 μl, 0.339 mmoles) and a solution of 4-(4′-difluoromethoxy-biphenyl-4-ylaminomethyl)-5-methyl-furan-2-carboxylic acid (171) (50 mg, 0.103 mmoles) in N,N-dimethylformamide (1.0 ml) were added to a stirred solution of 3,5-dimethyl-isoxazole-4-sulphonic acid amide (55 mg, 0.308 mmoles) in N,N-dime... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Carboxylic acid | Sulfonamide.Secondary amide | null | null | c1cnoc1.c1ccoc1.c1ccccc1.c1ccccc1 | HO- | CN(C=O)C | null | 16 | Cc1noc(C)c1S(N)(=O)=O.Cc1oc(C(=O)O)cc1CNc1ccc(-c2ccc(OC(F)F)cc2)cc1>CN(C=O)C>Cc1noc(C)c1S(=O)(=O)NC(=O)c1cc(CNc2ccc(-c3ccc(OC(F)F)cc3)cc2)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2e3d54351f6e4043af52017d3c0c5e4d | CI.COC(=O)c1cc(CNc2ccc(-c3ccc(OC(F)F)cc3)cc2)c(C)o1>>COC(=O)c1cc(CN(C)c2ccc(-c3ccc(OC(F)F)cc3)cc2)c(C)o1 | IC.C([O-])([O-])=O.[K+].[K+].COC(=O)C=1OC(=C(C1)CNC1=CC=C(C=C1)C1=CC=C(C=C1)OC(F)F)C>>COC(=O)C=1OC(=C(C1)CN(C)C1=CC=C(C=C1)C1=CC=C(C=C1)OC(F)F)C | I[CH3:10].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][NH:9][c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][c:18]([O:19][CH:20]([F:21])[F:22])[cH:23][cH:24]3)[cH:25][cH:26]2)[c:27]([CH3:28])[o:29]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH2:8][N:9]([CH3:10])[c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:... | CI.COC(=O)c1cc(CNc2ccc(-c3ccc(OC(F)F)cc3)cc2)c(C)o1 | COC(=O)c1cc(CN(C)c2ccc(-c3ccc(OC(F)F)cc3)cc2)c(C)o1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | e1587a52a1bca6a80c6048d43276d8bccf8d3e94e692e6b210e5fd3b22494187 | 7cc25fba33369069673bac5bd8fc404dc064da8d6c8cf4a77f21f4df0a617fe3 | c1ccc(-c2ccc(NCc3ccoc3)cc2)cc1 | I-[CH3;D1;+0:1].[#8;a:2]:[c:3]:[c:4]-[C:5]-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[#8;a:2]:[c:3]:[c:4]-[C:5]-[N;H0;D3;+0:6](-[CH3;D1;+0:1])-[c:7](:[c:8]):[c:9] | 63.8 | [{"value": 63.8, "product": "COC(=O)C=1OC(=C(C1)CN(C)C1=CC=C(C=C1)C1=CC=C(C=C1)OC(F)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 36 | HOUR | Iodomethane (91 mg, 0.64 mmoles) and potassium carbonate (88 mg, 0.64 mmoles) were added to a solution of 4-(4′-difluoromethoxy-biphenyl-4-ylaminomethyl)-5-methyl-furan-2-carboxylic acid methyl ester (170) (62 mg, 0.16 mmoles) in N,N-dimethylformamide (10 ml) and the mixture stirred at room temperature for 36 hours und... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | null | null | c1ccoc1.c1ccccc1.c1ccccc1 | HI | CN(C=O)C | null | 36 | CI.COC(=O)c1cc(CNc2ccc(-c3ccc(OC(F)F)cc3)cc2)c(C)o1>CN(C=O)C>COC(=O)c1cc(CN(C)c2ccc(-c3ccc(OC(F)F)cc3)cc2)c(C)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1f696ea19d0d449caca1cf27cb196449 | COC(=O)c1cc(CN(C)c2ccc(-c3ccc(OC(F)F)cc3)cc2)c(C)o1>>Cc1oc(C(=O)O)cc1CN(C)c1ccc(-c2ccc(OC(F)F)cc2)cc1 | FC(C(=O)O)(F)F.COC(=O)C=1OC(=C(C1)CN(C)C1=CC=C(C=C1)C1=CC=C(C=C1)OC(F)F)C>>FC(OC1=CC=C(C=C1)C1=CC=C(C=C1)N(C)CC=1C=C(OC1C)C(=O)O)F | C[O:7][C:5]([c:4]1[o:3][c:2]([CH3:1])[c:9]([CH2:10][N:11]([CH3:12])[c:13]2[cH:14][cH:15][c:16](-[c:17]3[cH:18][cH:19][c:20]([O:21][CH:22]([F:23])[F:24])[cH:25][cH:26]3)[cH:27][cH:28]2)[cH:8]1)=[O:6]>>[CH3:1][c:2]1[o:3][c:4]([C:5](=[O:6])[OH:7])[cH:8][c:9]1[CH2:10][N:11]([CH3:12])[c:13]1[cH:14][cH:15][c:16](-[c:17]2[cH:... | COC(=O)c1cc(CN(C)c2ccc(-c3ccc(OC(F)F)cc3)cc2)c(C)o1 | Cc1oc(C(=O)O)cc1CN(C)c1ccc(-c2ccc(OC(F)F)cc2)cc1 | null | null | O1CCCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ccc(NCc3ccoc3)cc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#8;a:5]>>[#8;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 17.7 | [{"value": 17.7, "product": "FC(OC1=CC=C(C=C1)C1=CC=C(C=C1)N(C)CC=1C=C(OC1C)C(=O)O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | HOUR | A solution of 4-{[(4′-difluoromethoxy-biphenyl-4-yl)-methyl-amino]-methyl}-5-methyl-furan-2-carboxylic acid methyl ester (175) (30 mg, 0.07 mmoles) in dry tetrahydrofuran (20 ml) was treated with potassium trimethylsilanoate (19 mg, 0.15 mmoles) and the mixture stirred under an argon atmosphere for 30 hours. Trifluoroa... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccoc1.c1ccccc1.c1ccccc1 | Other | O1CCCC1 | null | 30 | COC(=O)c1cc(CN(C)c2ccc(-c3ccc(OC(F)F)cc3)cc2)c(C)o1>O1CCCC1>Cc1oc(C(=O)O)cc1CN(C)c1ccc(-c2ccc(OC(F)F)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-281f019ab44e493bac9d647da6402ad8 | CC(C)=CCC/C(C)=C/C(=O)O.N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O>>CC(C)=CCC/C(C)=C/C(=O)NC1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O | C(\C=C(/C)\CCC=C(C)C)(=O)O.C(C)N(CC)CC.Cl.OC1[C@H](N)[C@@H](O)[C@@H](O)[C@H](O1)CO.ClC(=O)OCC(C)C>>C1([C@H](O)[C@@H](O)[C@@H](O)[C@H](O1)CO)NC(\C=C(/C)\CCC=C(C)C)=O | O[C:10](/[CH:9]=[C:7](/[CH2:6][CH2:5][CH:4]=[C:2]([CH3:1])[CH3:3])[CH3:8])=[O:11].[NH2:12][C@H:22]1[CH:13]([OH:23])[O:14][C@H:15]([CH2:16][OH:17])[C@H:18]([OH:19])[C@@H:20]1[OH:21]>>[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][CH2:6]/[C:7]([CH3:8])=[CH:9]/[C:10](=[O:11])[NH:12][CH:13]1[O:14][C@H:15]([CH2:16][OH:17])[C@H:18]([OH... | CC(C)=CCC/C(C)=C/C(=O)O.N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O | CC(C)=CCC/C(C)=C/C(=O)NC1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O | null | null | O.CC(=O)C.[OH-].[Na+].C1CCOC1 | Acylation | OtherReaction | 2a67fc59999fd518505897134e5e714168f09ef3b0471e4d1831375d1302921f | ef5d2f42d27e953f00e3f1ba0755384ec25f145a166ad3265dce19707549d74a | C1CCOCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])/[C:3]=[C:4](\[C;D1;H3:5])-[C:6]-[C:7]-[C:8]=[C:9].[NH2;D1;+0:10]-[C@@H;D3;+0:11]1-[C:12](-[O;D1;H1:13])-[C:14]-[C:15]-[#8:16]-[CH;D3;+0:17]-1-[OH;D1;+0:18]>>[C:9]=[C:8]-[C:7]-[C:6]/[C:4](-[C;D1;H3:5])=[C:3]/[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[CH;D3;+0:17]1-[#8:16]-[C:15]-[C:14]-[C... | 46 | [{"value": 46.0, "product": "C1([C@H](O)[C@@H](O)[C@@H](O)[C@H](O1)CO)NC(\\C=C(/C)\\CCC=C(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.8, "product": "C1([C@H](O)[C@@H](O)[C@@H](O)[C@H](O1)CO)NC(\\C=C(/C)\\CCC=C(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a THF (20 ml) solution containing geranic acid (0.84 g, 5 mmols), triethylamine (0.51 g, 5 mmols) was added and cooled to 0° C., into which a THF (5 ml) solution containing isobutyl chloroformate (0.68 g, 5 mmols) was added dropwise, followed by 30 minutes' stirring at 0° C. Then galactosamine hydrochloride (1.08 g,... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Secondary alcohol.Primary amine | Ether.Secondary amide.Secondary alcohol | C1CCOCC1 | C1CCOCC1 | C1CCOCC1 | HO- | O.CC(=O)C.[OH-].[Na+].C1CCOC1 | 0 | 0.5 | CC(C)=CCC/C(C)=C/C(=O)O.N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O>O.CC(=O)C.[OH-].[Na+].C1CCOC1>CC(C)=CCC/C(C)=C/C(=O)NC1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d5316dfe55c3453a90a3327d5fe4fda0 | CC(C)=CCC/C(C)=C/CN.CC(C)COC(=O)Cl.CCN(CC)CC.O=C(O)/C=C/C(=O)O>>CC(C)=CCC/C(C)=C/CNC(=O)/C=C/C(=O)NC/C=C(\C)CCC=C(C)C | C(\C=C\C(=O)O)(=O)O.C(C)N(CC)CC.C(\C=C(/C)\CCC=C(C)C)N.ClC(=O)OCC(C)C>>C(\C=C(/C)\CCC=C(C)C)NC(\C=C\C(=O)NC\C=C(/C)\CCC=C(C)C)=O | [CH3:1][C:2](=[CH:4][CH2:5][CH2:6]/[C:7]([CH3:8])=[CH:9]/[CH2:10][NH2:11])[CH3:28].Cl[C:12](O[CH2:25][CH:26]([CH3:3])[CH3:27])=[O:13].C[CH2:16][N:18]([CH2:19][CH3:20])[CH2:22][CH3:24].O=[C:21](O)/[CH:23]=[CH:15]/[C:14](O)=[O:17]>>[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][CH2:6]/[C:7]([CH3:8])=[CH:9]/[CH2:10][NH:11][C:12](=[O... | CC(C)=CCC/C(C)=C/CN.CC(C)COC(=O)Cl.CCN(CC)CC.O=C(O)/C=C/C(=O)O | CC(C)=CCC/C(C)=C/CNC(=O)/C=C/C(=O)NC/C=C(\C)CCC=C(C)C | null | null | O1CCCC1.O | C-C Coupling | OtherReaction | bc8288f693b3f5e1f83ea0c7d2621a7bdbc8ff31868257930c3cf41a0e293c05 | 9b04b435d4909f27aba13de39436efd4f6dbf84886a2b40e0be7f7a8729de693 | null | C-[CH2;D2;+0:1]-[N;H0;D3;+0:2](-[C:3]-[CH3;D1;+0:4])-[CH2;D2;+0:5]-[CH3;D1;+0:6].Cl-[C;H0;D3;+0:7](=[O;D1;H0:8])-O-[CH2;D2;+0:9]-[CH;D3;+0:10](-[C;D1;H3:11])-[CH3;D1;+0:12].O-[C;H0;D3;+0:13](=[O;H0;D1;+0:14])/[CH;D2;+0:15]=[CH;D2;+0:16]/[C;H0;D3;+0:17](-O)=O.[C;D1;H3:18]-[C;H0;D3;+0:19](-[CH3;D1;+0:20])=[C:21]-[C:22]-[... | 110.7 | [{"value": 55.0, "product": "C(\\C=C(/C)\\CCC=C(C)C)NC(\\C=C\\C(=O)NC\\C=C(/C)\\CCC=C(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 110.7, "product": "C(\\C=C(/C)\\CCC=C(C)C)NC(\\C=C\\C(=O)NC\\C=C(/C)\\CCC=C(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a tetrahydrofuran (THF) (20 ml) solution containing fumaric acid (0.58 g, 5 mmols), triethylamine (1.01 g, 10 mmols) was added and the solution was cooled to 0° C., into which a THF (5 ml) solution containing isobutyl chloroformate (1.53 g, 10 mmols) was added dropwise. As the addition was continued, white precipita... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carboxylic acid.Carboxylic acid.Ether.Primary amine.Tertiary amine | Secondary amide.Secondary amide | null | null | null | HCl | O1CCCC1.O | 0 | 0.5 | CC(C)=CCC/C(C)=C/CN.CC(C)COC(=O)Cl.CCN(CC)CC.O=C(O)/C=C/C(=O)O>O1CCCC1.O>CC(C)=CCC/C(C)=C/CNC(=O)/C=C/C(=O)NC/C=C(\C)CCC=C(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8a95bc2602d14bacb8ec28deb740f57f | CC(C)=CCC/C(C)=C/C(=O)O.N[C@@H](CS)C(=O)O>>CC(C)=CCC/C(C)=C/C(=O)N[C@@H](CS)C(=O)O | C(\C=C(/C)\CCC=C(C)C)(=O)O.C(C)N(CC)CC.ClC(=O)OCC(C)C.N[C@@H](CS)C(=O)O.Cl>>C(\C=C(/C)\CCC=C(C)C)(=O)N[C@@H](CS)C(=O)O | O[C:10](/[CH:9]=[C:7](/[CH2:6][CH2:5][CH:4]=[C:2]([CH3:1])[CH3:3])[CH3:8])=[O:11].[NH2:12][C@@H:13]([CH2:14][SH:15])[C:16](=[O:17])[OH:18]>>[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][CH2:6]/[C:7]([CH3:8])=[CH:9]/[C:10](=[O:11])[NH:12][C@@H:13]([CH2:14][SH:15])[C:16](=[O:17])[OH:18] | CC(C)=CCC/C(C)=C/C(=O)O.N[C@@H](CS)C(=O)O | CC(C)=CCC/C(C)=C/C(=O)N[C@@H](CS)C(=O)O | null | null | [OH-].[Na+].C1CCOC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | null | O-[C;H0;D3;+0:1](=[O;D1;H0:2])/[C:3]=[C:4](\[C;D1;H3:5])-[C:6]-[C:7]-[C:8]=[C:9].[C:10]-[C:11](-[NH2;D1;+0:12])-[C:13](=[O;D1;H0:14])-[O;D1;H1:15]>>[C:10]-[C:11](-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])/[C:3]=[C:4](\[C;D1;H3:5])-[C:6]-[C:7]-[C:8]=[C:9])-[C:13](=[O;D1;H0:14])-[O;D1;H1:15] | 20.5 | [{"value": 19.5, "product": "C(\\C=C(/C)\\CCC=C(C)C)(=O)N[C@@H](CS)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 20.5, "product": "C(\\C=C(/C)\\CCC=C(C)C)(=O)N[C@@H](CS)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a THF (20 ml) solution containing geranic acid (1.68 g, 10 mmols), triethylamine (1.01 g, 10 mmols) was added and cooled to 0° C., into which a THF (5 ml) solution of isobutyl chloroformate (1.37 g, 10 mmols) was added dropwise, followed by 30 minutes' stirring at 0° C. To the reaction mixture a solution of cysteine... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | null | HO- | [OH-].[Na+].C1CCOC1 | 0 | 0.5 | CC(C)=CCC/C(C)=C/C(=O)O.N[C@@H](CS)C(=O)O>[OH-].[Na+].C1CCOC1>CC(C)=CCC/C(C)=C/C(=O)N[C@@H](CS)C(=O)O |
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