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-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-716f9534c2df48828b24217a5065dbca | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.NCCC1=CCCc2ccccc21>>CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)NCCC1=CCCc2ccccc21 | C12C(C3CC(CC(C1)C3)C2)OC(=O)NC(CC2=CNC3=CC=CC=C23)(C(=O)O)C.Cl.C1(=CCCC2=CC=CC=C12)CCN>>C1(=CCCC2=CC=CC=C12)CCNC(C(C)(CC1=CNC2=CC=CC=C12)NC(OC1C2CC3CC(CC1C3)C2)=O)=O | O[C:27]([C:2]([CH3:1])([CH2:3][c:4]1[cH:5][nH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12)[NH:13][C:14](=[O:15])[O:16][CH:17]1[CH:18]2[CH2:19][CH:20]3[CH2:21][CH:22]([CH2:23]2)[CH2:24][CH:25]1[CH2:26]3)=[O:28].[NH2:29][CH2:30][CH2:31][C:32]1=[CH:33][CH2:34][CH2:35][c:36]2[cH:37][cH:38][cH:39][cH:40][c:41]21>>[CH3:1][C:2... | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.NCCC1=CCCc2ccccc21 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)NCCC1=CCCc2ccccc21 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NC(Cc1c[nH]c2ccccc12)C(=O)NCCC1=CCCc2ccccc21)OC1C2CC3CC(C2)CC1C3 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[#7:6]-[C:7]=[O;D1;H0:8].[C:9]=[C:10]-[C:11]-[C:12]-[NH2;D1;+0:13]>>[C:9]=[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[#7:6]-[C:7]=[O;D1;H0:8] | null | [] | null | null | null | null | Following the procedure of Example 70, the title compound was prepared from 0.50 g (1.26 mmol) of 2-adamantyloxycarbonyl-α-methyl-DL-tryptophan and 0.29 g (1.38 mmol) of 3,4-dihydro-1-naphthalene-ethanamine hydrochloride. The purified product after chromatography was obtained as a white foam, 0.41 g (59%); 1H NMR (CDCl... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2[nH]ccc2c1.C1=Cc2ccccc2CC1.C1C2CC3CC1CC(C2)C3 | HO- | null | null | null | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.NCCC1=CCCc2ccccc21>>CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)NCCC1=CCCc2ccccc21 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-656af9e4f60848a7981ea7b0d9518cf5 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.NCCc1cccs1>>CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)NCCc1cccs1 | C(C)N(CC)CC.Cl.S1C(=CC=C1)CCN.C12C(C3CC(CC(C1)C3)C2)OC(=O)NC(CC2=CNC3=CC=CC=C23)(C(=O)O)C.ON1N=NC2=C1C=CC=C2.CN(CCCN=C=NCC)C>>N1C=C(C2=CC=CC=C12)CC(C(NCCC=1SC=CC1)=O)(C)NC(OC1C2CC3CC(CC1C3)C2)=O | O[C:27]([C:2]([CH3:1])([CH2:3][c:4]1[cH:5][nH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12)[NH:13][C:14](=[O:15])[O:16][CH:17]1[CH:18]2[CH2:19][CH:20]3[CH2:21][CH:22]([CH2:23]2)[CH2:24][CH:25]1[CH2:26]3)=[O:28].[NH2:29][CH2:30][CH2:31][c:32]1[cH:33][cH:34][cH:35][s:36]1>>[CH3:1][C:2]([CH2:3][c:4]1[cH:5][nH:6][c:7]2[cH:8]... | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.NCCc1cccs1 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)NCCc1cccs1 | null | null | CN(C=O)C.C(C)(=O)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NC(Cc1c[nH]c2ccccc12)C(=O)NCCc1cccs1)OC1C2CC3CC(C2)CC1C3 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[#7:6]-[C:7]=[O;D1;H0:8].[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[#7:6]-[C:7]=[O;D1;H0:8] | 61 | [{"value": 61.0, "product": "N1C=C(C2=CC=CC=C12)CC(C(NCCC=1SC=CC1)=O)(C)NC(OC1C2CC3CC(CC1C3)C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.7, "product": "N1C=C(C2=CC=CC=C12)CC(C(NCCC=1SC=CC1)=O)(C)NC(OC1C2CC3CC(CC1C3)C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 2-adamantyloxycarbonyl-α-methyl-DL-tryptophan (0,401 g, 1.01 mmol) in dry ethyl acetate (6 mL) and N,N-dimethylformamide (4 mL) under nitrogen atmosphere was added 1-hydroxybenzotriazole (0.138 g, 1.02 mmol) followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (0.199 g, 1.04 mmol). this mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccsc1.c1ccc2[nH]ccc2c1.C1C2CC3CC1CC(C2)C3 | HO- | CN(C=O)C.C(C)(=O)OCC | null | 2 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.NCCc1cccs1>CN(C=O)C.C(C)(=O)OCC>CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)NCCc1cccs1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-61c6d8aabb5a41be87f76a5ca9c7a047 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.Cn1cccc1CCN>>Cn1cccc1CCNC(=O)C(C)(Cc1c[nH]c2ccccc12)NC(=O)OC1C2CC3CC(C2)CC1C3 | NCCC=1N(C=CC1)C.CN(CCCN=C=NCC)C.C12C(C3CC(CC(C1)C3)C2)OC(=O)NC(CC2=CNC3=CC=CC=C23)(C(=O)O)C.ON1N=NC2=C1C=CC=C2>>N1C=C(C2=CC=CC=C12)CC(C(=O)NCCC=1N(C=CC1)C)(C)NC(OC1C2CC3CC(CC1C3)C2)=O | O[C:10](=[O:11])[C:12]([CH3:13])([CH2:14][c:15]1[cH:16][nH:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]12)[NH:24][C:25](=[O:26])[O:27][CH:28]1[CH:29]2[CH2:30][CH:31]3[CH2:32][CH:33]([CH2:34]2)[CH2:35][CH:36]1[CH2:37]3.[CH3:1][n:2]1[cH:3][cH:4][cH:5][c:6]1[CH2:7][CH2:8][NH2:9]>>[CH3:1][n:2]1[cH:3][cH:4][cH:5][c:6]1[CH2:... | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.Cn1cccc1CCN | Cn1cccc1CCNC(=O)C(C)(Cc1c[nH]c2ccccc12)NC(=O)OC1C2CC3CC(C2)CC1C3 | null | null | CN(C=O)C.C(C)(=O)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NC(Cc1c[nH]c2ccccc12)C(=O)NCCc1ccc[nH]1)OC1C2CC3CC(C2)CC1C3 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[#7:6]-[C:7]=[O;D1;H0:8].[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:4]-[C:3](-[C;D1;H3:5])(-[#7:6]-[C:7]=[O;D1;H0:8])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:11]-[C:10]-[C:9] | null | [] | null | null | 2 | HOUR | To a solution of 2-adamantyloxycarbonyl-α-methyl-DL-tryptophan (0.401 g, 1.01 mmol) in dry ethyl acetate (4 mL) and N,N-dimethylformamide (4 mL) under nitrogen atmosphere was added 1-hydroxybenzotriazole (0.139 g, 1.03 mmol) followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (0.199 g, 1.04 mmol). This mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc[nH]1.c1ccc2[nH]ccc2c1.C1C2CC3CC1CC(C2)C3 | HO- | CN(C=O)C.C(C)(=O)OCC | null | 2 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.Cn1cccc1CCN>CN(C=O)C.C(C)(=O)OCC>Cn1cccc1CCNC(=O)C(C)(Cc1c[nH]c2ccccc12)NC(=O)OC1C2CC3CC(C2)CC1C3 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ec175e3168cb4a1d9c1c6ae6b0efcecf | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.NCCc1ccccn1>>CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)NCCc1ccccn1 | NCCC1=NC=CC=C1.Cl.CN(CCCN=C=NCC)C.C12C(C3CC(CC(C1)C3)C2)OC(=O)NC(CC2=CNC3=CC=CC=C23)(C(=O)O)C.ON1N=NC2=C1C=CC=C2>>N1C=C(C2=CC=CC=C12)CC(C(NCCC1=NC=CC=C1)=O)(C)NC(OC1C2CC3CC(CC1C3)C2)=O | O[C:27]([C:2]([CH3:1])([CH2:3][c:4]1[cH:5][nH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12)[NH:13][C:14](=[O:15])[O:16][CH:17]1[CH:18]2[CH2:19][CH:20]3[CH2:21][CH:22]([CH2:23]2)[CH2:24][CH:25]1[CH2:26]3)=[O:28].[NH2:29][CH2:30][CH2:31][c:32]1[cH:33][cH:34][cH:35][cH:36][n:37]1>>[CH3:1][C:2]([CH2:3][c:4]1[cH:5][nH:6][c:7]... | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.NCCc1ccccn1 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)NCCc1ccccn1 | null | null | CN(C=O)C.C(C)(=O)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NC(Cc1c[nH]c2ccccc12)C(=O)NCCc1ccccn1)OC1C2CC3CC(C2)CC1C3 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[#7:6]-[C:7]=[O;D1;H0:8].[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[#7:6]-[C:7]=[O;D1;H0:8] | 72.2 | [{"value": 72.0, "product": "N1C=C(C2=CC=CC=C12)CC(C(NCCC1=NC=CC=C1)=O)(C)NC(OC1C2CC3CC(CC1C3)C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.2, "product": "N1C=C(C2=CC=CC=C12)CC(C(NCCC1=NC=CC=C1)=O)(C)NC(OC1C2CC3CC(CC1C3)C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 2-adamantyloxycarbonyl-α-methyl-DL-tryptophan (0.400 g, 1.01 mmol) in ethyl acetate (6 mL) and N,N-dimethylformamide (4 mL) under nitrogen atmosphere was added 1-hydroxybenzotriazole (0.138 g, 1.02 mmol) followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.198 g, 1.03 mmol). This ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2[nH]ccc2c1.c1ccncc1.C1C2CC3CC1CC(C2)C3 | HO- | CN(C=O)C.C(C)(=O)OCC | null | 2 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.NCCc1ccccn1>CN(C=O)C.C(C)(=O)OCC>CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)NCCc1ccccn1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7194255956584fd99d5e7200184f0486 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.NCCc1c[nH]cn1>>CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)NCCc1c[nH]cn1 | C(C)N(CC)CC.Cl.Cl.NCCC1=CNC=N1.C12C(C3CC(CC(C1)C3)C2)OC(=O)NC(CC2=CNC3=CC=CC=C23)(C(=O)O)C.FC1=C(C(=C(C(=C1O)F)F)F)F.CN(CCCN=C=NCC)C>>N1C=NC(=C1)CCNC(C(C)(CC1=CNC2=CC=CC=C12)NC(OC1C2CC3CC(CC1C3)C2)=O)=O | O[C:27]([C:2]([CH3:1])([CH2:3][c:4]1[cH:5][nH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12)[NH:13][C:14](=[O:15])[O:16][CH:17]1[CH:18]2[CH2:19][CH:20]3[CH2:21][CH:22]([CH2:23]2)[CH2:24][CH:25]1[CH2:26]3)=[O:28].[NH2:29][CH2:30][CH2:31][c:32]1[cH:33][nH:34][cH:35][n:36]1>>[CH3:1][C:2]([CH2:3][c:4]1[cH:5][nH:6][c:7]2[cH:8]... | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.NCCc1c[nH]cn1 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)NCCc1c[nH]cn1 | null | null | CN(C=O)C.C(C)(=O)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NC(Cc1c[nH]c2ccccc12)C(=O)NCCc1c[nH]cn1)OC1C2CC3CC(C2)CC1C3 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[#7:6]-[C:7]=[O;D1;H0:8].[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[#7:6]-[C:7]=[O;D1;H0:8] | 47.3 | [{"value": 47.0, "product": "N1C=NC(=C1)CCNC(C(C)(CC1=CNC2=CC=CC=C12)NC(OC1C2CC3CC(CC1C3)C2)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.3, "product": "N1C=NC(=C1)CCNC(C(C)(CC1=CNC2=CC=CC=C12)NC(OC1C2CC3CC(CC1C3)C2)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 2-adamantyloxycarbonyl-α-methyl-DL-tryptophan (0.401 g, 1.01 mmol) in dry ethyl acetate (6 mL) and N,N-dimethylformamide (4 mL) under nitrogen atmosphere was added pentafluorophenol (0.189 g, 1.03 mmol) followed by 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide (0.200 g, 1.04 mmol). This mixture was st... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1c[nH]cn1.c1ccc2[nH]ccc2c1.C1C2CC3CC1CC(C2)C3 | HO- | CN(C=O)C.C(C)(=O)OCC | null | 2 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.NCCc1c[nH]cn1>CN(C=O)C.C(C)(=O)OCC>CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)NCCc1c[nH]cn1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-becfad45d9734a6d87f686999f99d161 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.NCCc1cnccn1>>CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)NCCc1cnccn1 | C(C)N(CC)CC.Cl.N1=C(C=NC=C1)CCN.C12C(C3CC(CC(C1)C3)C2)OC(=O)NC(CC2=CNC3=CC=CC=C23)(C(=O)O)C.O.ON1N=NC2=C1C=CC=C2.C1(CCCCC1)N=C=NC1CCCCC1>>N1C=C(C2=CC=CC=C12)CC(C(NCCC1=NC=CN=C1)=O)(C)NC(OC1C2CC3CC(CC1C3)C2)=O | O[C:27]([C:2]([CH3:1])([CH2:3][c:4]1[cH:5][nH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12)[NH:13][C:14](=[O:15])[O:16][CH:17]1[CH:18]2[CH2:19][CH:20]3[CH2:21][CH:22]([CH2:23]2)[CH2:24][CH:25]1[CH2:26]3)=[O:28].[NH2:29][CH2:30][CH2:31][c:32]1[cH:33][n:34][cH:35][cH:36][n:37]1>>[CH3:1][C:2]([CH2:3][c:4]1[cH:5][nH:6][c:7]2... | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.NCCc1cnccn1 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)NCCc1cnccn1 | null | null | O.C(C)(=O)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NC(Cc1c[nH]c2ccccc12)C(=O)NCCc1cnccn1)OC1C2CC3CC(C2)CC1C3 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[#7:6]-[C:7]=[O;D1;H0:8].[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[#7:6]-[C:7]=[O;D1;H0:8] | 63.2 | [{"value": 63.0, "product": "N1C=C(C2=CC=CC=C12)CC(C(NCCC1=NC=CN=C1)=O)(C)NC(OC1C2CC3CC(CC1C3)C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.2, "product": "N1C=C(C2=CC=CC=C12)CC(C(NCCC1=NC=CN=C1)=O)(C)NC(OC1C2CC3CC(CC1C3)C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.75 | HOUR | A room temperature solution of 0.40 g (1.01 mmol) of 2-adamantyloxycarbonyl-α-methyl-DL-tryptophan and 0.15 g (1.11 mmol) of 1-hydroxybenzotriazole hydrate in 15 mL of anhydrous ethyl acetate under N2 atmosphere was treated with 0.23 g (1.11 mmol) of 1,3-dicyclohexylcarbodiimide in one portion. The reaction was stirred... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2[nH]ccc2c1.c1cnccn1.C1C2CC3CC1CC(C2)C3 | HO- | O.C(C)(=O)OCC | null | 1.75 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.NCCc1cnccn1>O.C(C)(=O)OCC>CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)NCCc1cnccn1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7786619ae1dc47dd91ffb8bbbb049c69 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.NCCc1ccco1>>CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)NCCc1ccco1 | C(C)N(CC)CC.Cl.O1C(=CC=C1)CCN.C12C(C3CC(CC(C1)C3)C2)OC(=O)NC(CC2=CNC3=CC=CC=C23)(C(=O)O)C.O.ON1N=NC2=C1C=CC=C2.Cl.CN(CCCN=C=NCC)C>>O1C(=CC=C1)CCNC(C(C)(CC1=CNC2=CC=CC=C12)NC(OC1C2CC3CC(CC1C3)C2)=O)=O | O[C:27]([C:2]([CH3:1])([CH2:3][c:4]1[cH:5][nH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12)[NH:13][C:14](=[O:15])[O:16][CH:17]1[CH:18]2[CH2:19][CH:20]3[CH2:21][CH:22]([CH2:23]2)[CH2:24][CH:25]1[CH2:26]3)=[O:28].[NH2:29][CH2:30][CH2:31][c:32]1[cH:33][cH:34][cH:35][o:36]1>>[CH3:1][C:2]([CH2:3][c:4]1[cH:5][nH:6][c:7]2[cH:8]... | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.NCCc1ccco1 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)NCCc1ccco1 | null | null | O.CN(C=O)C.C(C)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NC(Cc1c[nH]c2ccccc12)C(=O)NCCc1ccco1)OC1C2CC3CC(C2)CC1C3 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[#7:6]-[C:7]=[O;D1;H0:8].[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[#7:6]-[C:7]=[O;D1;H0:8] | 70 | [{"value": 70.0, "product": "O1C(=CC=C1)CCNC(C(C)(CC1=CNC2=CC=CC=C12)NC(OC1C2CC3CC(CC1C3)C2)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.9, "product": "O1C(=CC=C1)CCNC(C(C)(CC1=CNC2=CC=CC=C12)NC(OC1C2CC3CC(CC1C3)C2)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.75 | HOUR | A room temperature solution of 0.30 g (0.76 mmol) of 2-adamantyloxycarbonyl-α-methyl-DL-tryptophan and 0.11 g (0.81 mmol) of 1-hydroxybenzotriazole hydrate in 10 mL of anhydrous N,N-dimethylformamide under N2 atmosphere was treated with 0.16 g (0.83 mmol 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in on... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccoc1.c1ccc2[nH]ccc2c1.C1C2CC3CC1CC(C2)C3 | HO- | O.CN(C=O)C.C(C)OCC | null | 1.75 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.NCCc1ccco1>O.CN(C=O)C.C(C)OCC>CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)NCCc1ccco1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-05e081f90841429c9b821ae03ea8e13a | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.NCCc1ccc2ccccc2n1>>CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)NCCc1ccc2ccccc2n1 | NCCC1=NC2=CC=CC=C2C=C1.C12C(C3CC(CC(C1)C3)C2)OC(=O)NC(CC2=CNC3=CC=CC=C23)(C(=O)O)C.CN1CCOCC1.ClC(=O)OCC(C)C>>N1C=C(C2=CC=CC=C12)CC(C(=O)NCCC1=NC2=CC=CC=C2C=C1)(C)NC(OC1C2CC3CC(CC1C3)C2)=O | O[C:27]([C:2]([CH3:1])([CH2:3][c:4]1[cH:5][nH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12)[NH:13][C:14](=[O:15])[O:16][CH:17]1[CH:18]2[CH2:19][CH:20]3[CH2:21][CH:22]([CH2:23]2)[CH2:24][CH:25]1[CH2:26]3)=[O:28].[NH2:29][CH2:30][CH2:31][c:32]1[cH:33][cH:34][c:35]2[cH:36][cH:37][cH:38][cH:39][c:40]2[n:41]1>>[CH3:1][C:2]([C... | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.NCCc1ccc2ccccc2n1 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)NCCc1ccc2ccccc2n1 | null | null | C1CCOC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NC(Cc1c[nH]c2ccccc12)C(=O)NCCc1ccc2ccccc2n1)OC1C2CC3CC(C2)CC1C3 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[#7:6]-[C:7]=[O;D1;H0:8].[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[#7:6]-[C:7]=[O;D1;H0:8] | 17.3 | [{"value": 17.0, "product": "N1C=C(C2=CC=CC=C12)CC(C(=O)NCCC1=NC2=CC=CC=C2C=C1)(C)NC(OC1C2CC3CC(CC1C3)C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 17.3, "product": "N1C=C(C2=CC=CC=C12)CC(C(=O)NCCC1=NC2=CC=CC=C2C=C1)(C)NC(OC1C2CC3CC(CC1C3)C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | -22 | CELSIUS | 1 | HOUR | To a stirred solution of 2-adamantyloxycarbonyl-α-methyl-DL-tryptophan (1.59 g, 4.0 mmole) in dry THF (50 mL) at -22° C. was added N-methylmorpholine (0.644 g, 6.3 mmole) and isobutyl chloroformate (0.632 g, 4.6 mmole). The mixture was stirred at -22° C. for 1 hour and then a solution of 2-(2-aminoethyl)quinoline (0.69... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2[nH]ccc2c1.c1ccc2ncccc2c1.C1C2CC3CC1CC(C2)C3 | HO- | C1CCOC1 | -22 | 1 | CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)O.NCCc1ccc2ccccc2n1>C1CCOC1>CC(Cc1c[nH]c2ccccc12)(NC(=O)OC1C2CC3CC(C2)CC1C3)C(=O)NCCc1ccc2ccccc2n1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2045145affa643dba59de3928e171cbb | COC(=O)C(N)Cc1c[nH]c2ccccc12.C[Si](C)(C)CCOCCl>>COC(=O)C(Cc1c[nH]c2ccccc12)NCOC(C)[Si](C)(C)C | C[Si](C)(C)CCOCCl.C1CCOC1.COC(=O)C(CC1=CNC2=CC=CC=C21)N.C(C)(C)[N-]C(C)C.[Li+].C1CCOC1.C1CCOC1>>COC(C(NCOC(C)[Si](C)(C)C)CC1=CNC2=CC=CC=C12)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][nH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]12)[NH2:16].Cl[CH2:17][O:18][CH2:20][CH2:19][Si:21]([CH3:22])([CH3:23])[CH3:24]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][nH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]12)[NH:16][CH2:17][O:18][CH:19]([CH3:20])[S... | COC(=O)C(N)Cc1c[nH]c2ccccc12.C[Si](C)(C)CCOCCl | COC(=O)C(Cc1c[nH]c2ccccc12)NCOC(C)[Si](C)(C)C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b600a81df87bea1685df54aaf8b30bd23674e9b7dd2a3cc8662e71bd3684ebef | d995b0d46e4aacf6b403d700b3e57edde7ae1aa34d450d1418ad3604b33a8a71 | c1ccc2[nH]ccc2c1 | Cl-[CH2;D2;+0:1]-[O;H0;D2;+0:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[#14:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].[C:9]-[C:10](-[NH2;D1;+0:11])-[C:12](=[O;D1;H0:13])-[#8:14]-[C;D1;H3:15]>>[C:9]-[C:10](-[NH;D2;+0:11]-[CH2;D2;+0:1]-[O;H0;D2;+0:2]-[CH;D3;+0:4](-[CH3;D1;+0:3])-[#14:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8])-[C:... | 44 | [{"value": 44.0, "product": "COC(C(NCOC(C)[Si](C)(C)C)CC1=CNC2=CC=CC=C12)=O", "details": "PERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | 45 | MINUTE | A solution of DL-tryptophan methyl esterbenzaldimine (4.0 g, 13 mmol) in 30 mL THF was added over 15 minutes to a mixture of 20.2 mL lithiumdiisopropylamide (10% suspension in hexan) and 70 mL dry THF, cooled to -10° C. under nitrogen atmosphere. The stirring was continued for an additional 45 minutes, keeping the temp... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Primary amine | Ether.Secondary amine | null | null | c1ccc2[nH]ccc2c1 | HCl | null | -10 | 0.75 | COC(=O)C(N)Cc1c[nH]c2ccccc12.C[Si](C)(C)CCOCCl>>COC(=O)C(Cc1c[nH]c2ccccc12)NCOC(C)[Si](C)(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c16042dc65ff40eb8e55e17df4d32ef8 | COC(=O)C(Cc1c[nH]c2ccccc12)NCOC(C)[Si](C)(C)C.O=C(Cl)OC1C2CC3CC(C2)CC1C3>>COC(=O)C(Cc1c[nH]c2ccccc12)N(COC(C)[Si](C)(C)C)C(=O)OC1C2CC3CC(C2)CC1C3 | COC(C(NCOC(C)[Si](C)(C)C)CC1=CNC2=CC=CC=C12)=O.C(C)(C)N(CC)C(C)C.C12C(C3CC(CC(C1)C3)C2)OC(=O)Cl>>COC(C(N(C(=O)OC1C2CC3CC(CC1C3)C2)COC(C)[Si](C)(C)C)CC2=CNC3=CC=CC=C23)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][nH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]12)[NH:16][CH2:17][O:18][CH:19]([CH3:20])[Si:21]([CH3:22])([CH3:23])[CH3:24].Cl[C:25](=[O:26])[O:27][CH:28]1[CH:29]2[CH2:30][CH:31]3[CH2:32][CH:33]([CH2:34]2)[CH2:35][CH:36]1[CH2:37]3>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:... | COC(=O)C(Cc1c[nH]c2ccccc12)NCOC(C)[Si](C)(C)C.O=C(Cl)OC1C2CC3CC(C2)CC1C3 | COC(=O)C(Cc1c[nH]c2ccccc12)N(COC(C)[Si](C)(C)C)C(=O)OC1C2CC3CC(C2)CC1C3 | null | null | O.C1CCOC1 | Protection | N-alkylation of secondary amines with alkyl halides | 496a200c7c2fc7c000296e03cda40efb8e258ccaeb02fa999285bf74ddc49346 | d86dc1e6d0e089b3444b62ddfcf4c4822bdac4b60e628553036562518c29adcd | O=C(NCCc1c[nH]c2ccccc12)OC1C2CC3CC(C2)CC1C3 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[#8:5]-[C:6]-[NH;D2;+0:7]-[C:8](-[C:9])-[C:10](=[O;D1;H0:11])-[#8:12]-[C;D1;H3:13]>>[#8:5]-[C:6]-[N;H0;D3;+0:7](-[C:8](-[C:9])-[C:10](=[O;D1;H0:11])-[#8:12]-[C;D1;H3:13])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4] | 67.8 | [{"value": 67.8, "product": "COC(C(N(C(=O)OC1C2CC3CC(CC1C3)C2)COC(C)[Si](C)(C)C)CC2=CNC3=CC=CC=C23)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.8, "product": "COC(C(N(C(=O)OC1C2CC3CC(CC1C3)C2)COC(C)[Si](C)(C)C)CC2=CNC3=CC=CC=C23)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A mixture of α-trimethylsilylethoxymethyl-DL-tryptophan methyl ester (1.0 g, 2.8 mmol), diisopropylethylamine (0.4 g, 3 mmol) and 2-adarnantylchloroformate (0.65 g, 3 mmol) in 20 mL dry THF was stirred at room temperature for 4 hours. The reaction mixture was diluted with distilled water and extracted with ethyl acetat... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amine | Carbamic ester | null | null | c1ccc2[nH]ccc2c1.C1C2CC3CC1CC(C2)C3 | HCl | O.C1CCOC1 | null | 4 | COC(=O)C(Cc1c[nH]c2ccccc12)NCOC(C)[Si](C)(C)C.O=C(Cl)OC1C2CC3CC(C2)CC1C3>O.C1CCOC1>COC(=O)C(Cc1c[nH]c2ccccc12)N(COC(C)[Si](C)(C)C)C(=O)OC1C2CC3CC(C2)CC1C3 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4a62f664045b4f719a06c2ba54a774ab | COC(=O)C(Cc1c[nH]c2ccccc12)N(COC(C)[Si](C)(C)C)C(=O)OC1C2CC3CC(C2)CC1C3>>CC(OCN(C(=O)OC1C2CC3CC(C2)CC1C3)C(Cc1c[nH]c2ccccc12)C(=O)O)[Si](C)(C)C | Cl.COC(C(N(C(=O)OC1C2CC3CC(CC1C3)C2)COC(C)[Si](C)(C)C)CC2=CNC3=CC=CC=C23)=O.[Li+].[OH-].O1CCOCC1>>C12C(C3CC(CC(C1)C3)C2)OC(=O)N(C(CC2=CNC3=CC=CC=C23)C(=O)O)COC(C)[Si](C)(C)C | C[O:32][C:30]([CH:19]([N:5]([CH2:4][O:3][CH:2]([CH3:1])[Si:33]([CH3:34])([CH3:35])[CH3:36])[C:6](=[O:7])[O:8][CH:9]1[CH:10]2[CH2:11][CH:12]3[CH2:13][CH:14]([CH2:15]2)[CH2:16][CH:17]1[CH2:18]3)[CH2:20][c:21]1[cH:22][nH:23][c:24]2[cH:25][cH:26][cH:27][cH:28][c:29]12)=[O:31]>>[CH3:1][CH:2]([O:3][CH2:4][N:5]([C:6](=[O:7])[... | COC(=O)C(Cc1c[nH]c2ccccc12)N(COC(C)[Si](C)(C)C)C(=O)OC1C2CC3CC(C2)CC1C3 | CC(OCN(C(=O)OC1C2CC3CC(C2)CC1C3)C(Cc1c[nH]c2ccccc12)C(=O)O)[Si](C)(C)C | null | null | O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(NCCc1c[nH]c2ccccc12)OC1C2CC3CC(C2)CC1C3 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 91.8 | [{"value": 91.7, "product": "C12C(C3CC(CC(C1)C3)C2)OC(=O)N(C(CC2=CNC3=CC=CC=C23)C(=O)O)COC(C)[Si](C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.8, "product": "C12C(C3CC(CC(C1)C3)C2)OC(=O)N(C(CC2=CNC3=CC=CC=C23)C(=O)O)COC(C)[Si](C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 16 | HOUR | A mixture of N-[(2-adamantyloxy)carbonyl]-α-trimethylsilylethoxymethyl-DL-tryptophan methyl ester (4.5 g, 8.5 mmol), LiOH (0.22 g, 9.1 mmol), dioxane (90 mL), and water (30 mL) was stirred at 60° C. for 16 hours. After cooling, the reaction mixture was acidified to pH 4 with 1N hydrochloric acid and extracted with ethy... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2[nH]ccc2c1.C1C2CC3CC1CC(C2)C3 | Other | O | 60 | 16 | COC(=O)C(Cc1c[nH]c2ccccc12)N(COC(C)[Si](C)(C)C)C(=O)OC1C2CC3CC(C2)CC1C3>O>CC(OCN(C(=O)OC1C2CC3CC(C2)CC1C3)C(Cc1c[nH]c2ccccc12)C(=O)O)[Si](C)(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-57f8129fa3464cad91a4662f4e8ab2fb | COC(=O)C(Cc1c[nH]c2ccccc12)NCOC(C)[Si](C)(C)C>>COC(=O)C(N)(CO)Cc1c[nH]c2ccccc12 | COC(C(NCOC(C)[Si](C)(C)C)CC1=CNC2=CC=CC=C12)=O.C(C)(=O)OCC>>COC(C(N)(CC1=CNC2=CC=CC=C12)CO)=O | CC([Si](C)(C)C)[O:8][CH2:7][NH:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:9][c:10]1[cH:11][nH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12>>[CH3:1][O:2][C:3](=[O:4])[C:5]([NH2:6])([CH2:7][OH:8])[CH2:9][c:10]1[cH:11][nH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12 | COC(=O)C(Cc1c[nH]c2ccccc12)NCOC(C)[Si](C)(C)C | COC(=O)C(N)(CO)Cc1c[nH]c2ccccc12 | null | null | FC(C(=O)O)(F)F | Miscellaneous | OtherReaction | f4a1a9f21e7e8515dc7a4b1f8faa9b0cbf9a43438874da739540d6f45e6febbd | da56836e50fc8ebc4ed3ba37b3d761a3463c51e4e2154a888c5f4909cc73f12b | c1ccc2[nH]ccc2c1 | C-C(-[O;H0;D2;+0:1]-[CH2;D2;+0:2]-[NH;D2;+0:3]-[CH;D3;+0:4](-[C:5]-[c:6]:[c:7]:[#7;a:8])-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12])-[Si](-C)(-C)-C>>[#7;a:8]:[c:7]:[c:6]-[C:5]-[C;H0;D4;+0:4](-[NH2;D1;+0:3])(-[CH2;D2;+0:2]-[OH;D1;+0:1])-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12] | null | [] | null | null | null | null | α-Trimethylsilylethoxymethyl-DL-tryptophan methyl ester (1.0 g, 2.8 mmol) was stirred for 48 hours at room temperature in trifluoroacetic acid (10 mL). After evaporation of the acid in vacuo, the oily residue was treated with aqueous sodium bicarbonate and extracted with ethyl acetate. The organic layer was dried over ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Secondary amine.Silyl protective group | Ester.Primary alcohol.Primary amine | null | null | c1ccc2[nH]ccc2c1 | Other | FC(C(=O)O)(F)F | null | null | COC(=O)C(Cc1c[nH]c2ccccc12)NCOC(C)[Si](C)(C)C>FC(C(=O)O)(F)F>COC(=O)C(N)(CO)Cc1c[nH]c2ccccc12 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e43d263a87e646cca91cfc51f8006d76 | CCOC(=O)c1cc2ccccc2[nH]1.Cc1ccc(S(=O)(=O)Cl)cc1>>CCOC(=O)c1cc2ccccc2n1S(=O)(=O)c1ccc(C)cc1 | [H-].[Na+].C1(=CC=C(C=C1)S(=O)(=O)Cl)C.C(C)OC(=O)C=1NC2=CC=CC=C2C1>>C(C)OC(=O)C=1N(C2=CC=CC=C2C1)S(=O)(=O)C1=CC=C(C=C1)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[nH:14]1.Cl[S:15](=[O:16])(=[O:17])[c:18]1[cH:19][cH:20][c:21]([CH3:22])[cH:23][cH:24]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[n:14]1[S:15](=[O:16])(=[O:17])[c:18]1[cH:19][cH:20][c:21]([CH3... | CCOC(=O)c1cc2ccccc2[nH]1.Cc1ccc(S(=O)(=O)Cl)cc1 | CCOC(=O)c1cc2ccccc2n1S(=O)(=O)c1ccc(C)cc1 | null | null | C1CCOC1 | Acylation | OtherReaction | 1f9175819c9c0179267ecae12f340317ed0385d3996f36daaf36cb61a5ef4625 | b7cf703ff8ec1befb0c6e5230d29d7904f3e22c3606b15633c7e7a7fc4abca48 | O=S(=O)(c1ccccc1)n1ccc2ccccc21 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[c:11]1:[c:12]:[c:13]:[c:14](:[c:15]):[nH;D2;+0:16]:1>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[c:11]1:[c:12]:[c:13]:[c:14](:[c:15]):[n;H0;D3;+0:16]:1-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | 30 | CELSIUS | null | null | To a stirred suspension of sodium hydride (3.7 g, 120 mmol, 80% in paraffin oil) in dry THF (75 mL), a solution of indol-2-carboxylic acid ethyl ester (18.9 g, 100 mmol) in dry THF (75 mL) was added in 1 hour with stirring while the inner temperature was maintained under 30° C. The reaction mixture was stirred for 30 m... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Sulfonyl halide | Tosylate | c1ccc2[nH]ccc2c1 | c1cc2ccccc2[nH]1 | c1cc2ccccc2[nH]1.c1ccccc1 | HCl | C1CCOC1 | 30 | null | CCOC(=O)c1cc2ccccc2[nH]1.Cc1ccc(S(=O)(=O)Cl)cc1>C1CCOC1>CCOC(=O)c1cc2ccccc2n1S(=O)(=O)c1ccc(C)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-bd07e98aceef4b509d4e39b6ba9624c9 | CC1(C)CCC(C)(C)c2cc(C(=O)CBr)ccc21>>CC1(C)CCC(C)(C)c2ccccc21 | BrCC(=O)C=1C=C2C(CCC(C2=CC1)(C)C)(C)C.SCCS(=O)(=O)O.[Na].C([O-])([O-])=O.[K+].[K+]>>[Na].CC1(CCC(C2=CC=CC=C12)(C)C)C | O=C(CBr)[c:11]1[cH:10][c:9]2[c:14]([cH:13][cH:12]1)[C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][C:6]2([CH3:7])[CH3:8]>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6]([CH3:7])([CH3:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]21 | CC1(C)CCC(C)(C)c2cc(C(=O)CBr)ccc21 | CC1(C)CCC(C)(C)c2ccccc21 | null | null | O.CN(C)C=O.C(C)(=O)OCC.C1CCOC1 | Reduction | OtherReaction | 5ab4144bb99e4b2d73510be0cdfcb7cadb6ac496474c2b2bde8c6a8b2cda5acf | a90507cbf9a8f6b61ec3939c06e1d4feba68ffc1aa9586e1ab836849ec480723 | c1ccc2c(c1)CCCC2 | Br-C-C(=O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]>>[c:5]:[c:4]:[cH;D2;+0:1]:[c:2]:[c:3] | null | [] | null | null | 30 | MINUTE | To a solution of 6-(bromoacetyl)-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene (12) (15.5 mg, 0.050 mmol) in DMF (0.13 mL) and THF (0.13 mL) was added a freshly prepared solution of 2-mercapto-1-ethanesulfonic acid, sodium salt (2) (25 mg, 0.15 mmol) and potassium carbonate (21 mg, 0.15 mmol) in water (0.15 mL) at ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | null | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | HBr | O.CN(C)C=O.C(C)(=O)OCC.C1CCOC1 | null | 0.5 | CC1(C)CCC(C)(C)c2cc(C(=O)CBr)ccc21>O.CN(C)C=O.C(C)(=O)OCC.C1CCOC1>CC1(C)CCC(C)(C)c2ccccc21 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d0e5da991214455380f3f6ed9e4608b4 | O=S(=O)([O-])[O-].[Cu]>>O=S(=O)([O-])[O-].[Cu+2] | S(=O)(=O)([O-])[O-].[Cu].C([O-])([O-])=O.[Cl-].[N+](=O)([O-])[O-].[Cu].C(CC(O)(C(=O)O)CC(=O)O)(=O)O.P(=O)([O-])([O-])[O-]>>S(=O)(=O)([O-])[O-].[Cu+2].C(CC(O)(C(=O)O)CC(=O)O)(=O)O | [O:14]=[S:15](=[O:16])([O-:17])[O-:18].[Cu:19]>>[O:14]=[S:15](=[O:16])([O-:17])[O-:18].[Cu+2:19] | O=S(=O)([O-])[O-].[Cu] | O=S(=O)([O-])[O-].[Cu+2] | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | [Cu;H0;D0;+0:1]>>[Cu+2;H0;D0:1] | null | [] | null | null | null | null | This example presents a synopsis of biocidal solution design calculations for a biocidal solution comprised of citric acid (the ligand, or complexing agent) and copper. One gallon of sewage effluent containing bacteria could be treated with one drop of stock solution prepared as follows. For this example, a biocide sol... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | null | null | null | O=S(=O)([O-])[O-].[Cu]>>O=S(=O)([O-])[O-].[Cu+2] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6cbbb1d8fe334f629a24aeb25dde05cd | O=P1([O-])OP(=O)([O-])OP(=O)([O-])OP(=O)([O-])OP(=O)([O-])OP(=O)([O-])O1.[Na+].[Na+]>>O=C([O-])[O-].OO.OO.[Na+].[Na+] | C([O-])([O-])=O.[Na+].[Na+].OO.[O-]P1(=O)OP(=O)(OP(=O)(OP(=O)(OP(=O)(OP(=O)(O1)[O-])[O-])[O-])[O-])[O-].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+]>>C(=O)([O-])[O-].C(=O)([O-])[O-].OO.OO.OO.[Na+].[Na+].[Na+].[Na+] | O=P1([O-])OP(=O)([O-:5])OP(=O)([O-:9])OP([O-:11])(=[O:12])[O:8]P(=O)([O-:7])OP(=O)([O-:10])O1.[Na+:15].[Na+:17]>>[O:5]=[C:6]([O-:7])[O-:8].[OH:9][OH:10].[OH:11][OH:12].[Na+:15].[Na+:17] | O=P1([O-])OP(=O)([O-])OP(=O)([O-])OP(=O)([O-])OP(=O)([O-])OP(=O)([O-])O1.[Na+].[Na+] | O=C([O-])[O-].OO.OO.[Na+].[Na+] | null | null | null | Acylation | OtherReaction | ec059456643c79f498e89d81205a797fefe65415b128fcac155699487a6d8c63 | 1d95aa8c02f655bb938e918f8b627c35a333785825d3cc1b76b181c1027d234a | null | O=P1(-[O-;H0;D1:1])-O-P(=O)(-[O-])-O-P(=O)(-[O-;H0;D1:2])-O-P(=O)(-[O-;H0;D1:3])-O-P(-[O-;H0;D1:4])(=[O;H0;D1;+0:5])-[O;H0;D2;+0:6]-P(=O)(-[O-;H0;D1:7])-O-1>>[O-;H0;D1:7]-[C:8](-[O-;H0;D1:6])=[O;H0;D1;+0:2].[OH;D1;+0:1]-[OH;D1;+0:3].[OH;D1;+0:4]-[OH;D1;+0:5] | null | [] | null | null | null | null | Wet sodium percarbonate salt was prepared in an operation according to the process described in DE-PS 28 00 760. After reacting sodium carbonate with hydrogen peroxide in a mother liquor containing kitchen salt and sodium hexametaphosphate and crystallising the sodium percarbonate, the latter was separated as far as po... | 10.6084/m9.figshare.5104873.v1 | null | null | Peroxide.Peroxide | O1POPOPOPOPOP1 | null | null | Other | null | null | null | O=P1([O-])OP(=O)([O-])OP(=O)([O-])OP(=O)([O-])OP(=O)([O-])OP(=O)([O-])O1.[Na+].[Na+]>>O=C([O-])[O-].OO.OO.[Na+].[Na+] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b50217a351b14b8aae4981607e137ab9 | OO.[Na+]>>O=C([O-])[O-].OO.OO.OO.[Na+].[Na+].[Na+] | C([O-])([O-])=O.[Na+].[Na+].OO>>C(=O)([O-])[O-].C(=O)([O-])[O-].OO.OO.OO.[Na+].[Na+].[Na+].[Na+] | [OH:9][OH:10].[Na+:16]>>[O:5]=[C:6]([O-:7])[O-:8].[OH:9][OH:10].[OH:11][OH:12].[OH:13][OH:14].[Na+:16].[Na+:17].[Na+:18] | OO.[Na+] | O=C([O-])[O-].OO.OO.OO.[Na+].[Na+].[Na+] | null | null | null | Acylation | OtherReaction | 0d3f6ecfc31a6f72a96f721a439b5ea2b3b75c89778d8abbdc59cdc1f5118296 | 1d95aa8c02f655bb938e918f8b627c35a333785825d3cc1b76b181c1027d234a | null | null | null | [] | null | null | null | null | A method for the preparation of stabilized sodium percarbonate comprising forming a sodium percarbonate core by reacting sodium carbonate with hydrogen peroxide in aqueous phase, crystallizing the resulting sodium percarbonate to obtain a wet sodium percarbonate having mother liquor adhering thereto, spraying said wet ... | 10.6084/m9.figshare.5104873.v1 | null | null | Peroxide.Peroxide | null | null | null | null | null | null | null | OO.[Na+]>>O=C([O-])[O-].OO.OO.OO.[Na+].[Na+].[Na+] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-091fa4e5f2d948a59c39c08379c63ae5 | COc1ccc(CSC(C)(C)C(=O)NCCN(CCNC(=O)C(C)(C)SCc2ccc(OC)cc2)Cc2ccc(N)cc2)cc1.S=C(Cl)Cl>>COc1ccc(CSC(C)(C)C(=O)NCCN(CCNC(=O)C(C)(C)SCc2ccc(OC)cc2)Cc2ccc(N=C=S)cc2)cc1 | COC1=CC=C(CSC(C(=O)NCCN(CCNC(C(C)(SCC2=CC=C(C=C2)OC)C)=O)CC2=CC=C(C=C2)N)(C)C)C=C1.C(=S)(Cl)Cl>>COC1=CC=C(CSC(C(=O)NCCN(CCNC(C(C)(SCC2=CC=C(C=C2)OC)C)=O)CC2=CC=C(C=C2)N=C=S)(C)C)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][C:9]([CH3:10])([CH3:11])[C:12](=[O:13])[NH:14][CH2:15][CH2:16][N:17]([CH2:18][CH2:19][NH:20][C:21](=[O:22])[C:23]([CH3:24])([CH3:25])[S:26][CH2:27][c:28]2[cH:29][cH:30][c:31]([O:32][CH3:33])[cH:34][cH:35]2)[CH2:36][c:37]2[cH:38][cH:39][c:40]([NH2:41])[cH:44][cH:45]2)[cH:... | COc1ccc(CSC(C)(C)C(=O)NCCN(CCNC(=O)C(C)(C)SCc2ccc(OC)cc2)Cc2ccc(N)cc2)cc1.S=C(Cl)Cl | COc1ccc(CSC(C)(C)C(=O)NCCN(CCNC(=O)C(C)(C)SCc2ccc(OC)cc2)Cc2ccc(N=C=S)cc2)cc1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | Amine and thiophosgene to isothiocyanate | 1226380c52141f79542a4f85564c11e38ca245efc80be1557b635219a638388c | e5752ca9983a57ab07a0b76a5c8a57a6667ab2cd460616b960134623ec0fce31 | O=C(CSCc1ccccc1)NCCN(CCNC(=O)CSCc1ccccc1)Cc1ccccc1 | Cl-[C;H0;D3;+0:1](-Cl)=[S;D1;H0:2].[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[S;D1;H0:2]=[C;H0;D2;+0:1]=[N;H0;D2;+0:3]-[c:4](:[c:5]):[c:6] | 117.3 | [{"value": 116.0, "product": "COC1=CC=C(CSC(C(=O)NCCN(CCNC(C(C)(SCC2=CC=C(C=C2)OC)C)=O)CC2=CC=C(C=C2)N=C=S)(C)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 117.3, "product": "COC1=CC=C(CSC(C(=O)NCCN(CCNC(C(C)(SCC2=CC=C(C=C2)OC)C)=O)CC2=CC=C(C=C2)N=C=S)(C)C)C=C1", "details": "CALCULATEDPERCENTYIELD... | null | null | 1 | HOUR | To a round bottom flask with the aniline 20 (55.7 mg, 0.0853 mmol) and dichloromethane (5 mL) was added 0.2011M solution of thiophosgene (0.42 mL, 0.0845 mmol) in dichloromethane. The heterogeneous reaction mixture was stirred at room temperature for 1 hour and the solvent was removed in vacuo to give the isothiocyanat... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Alkenyl halide.Primary amine | Isothiocyanate | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | ClCCl | null | 1 | COc1ccc(CSC(C)(C)C(=O)NCCN(CCNC(=O)C(C)(C)SCc2ccc(OC)cc2)Cc2ccc(N)cc2)cc1.S=C(Cl)Cl>ClCCl>COc1ccc(CSC(C)(C)C(=O)NCCN(CCNC(=O)C(C)(C)SCc2ccc(OC)cc2)Cc2ccc(N=C=S)cc2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7dd6ddcd9fdf4d37b3f1ccc1a56b5f96 | CC(N)N1CCN(C)CC(C)(C)SSC(C)(C)CN(C)CC1.NCCN(CCN)CCN>>CN(C)CCN1CCN(C)CC(C)(C)SSC(C)(C)CN(C)CC1 | CC1(SSC(CN(CCN(CCN(C1)C)C(C)N)C)(C)C)C.NCCN(CCN)CCN>>CN(C)CCN1CCN(CC(SSC(CN(CC1)C)(C)C)(C)C)C | N[CH:5]([CH3:4])[N:6]1[CH2:7][CH2:8][N:9]([CH3:10])[CH2:11][C:12]([CH3:13])([CH3:14])[S:15][S:16][C:17]([CH3:18])([CH3:19])[CH2:20][N:21]([CH3:22])[CH2:23][CH2:24]1.NCC[N:2]([CH2:1]CN)[CH2:3]CN>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][N:9]([CH3:10])[CH2:11][C:12]([CH3:13])([CH3:14])[S:15][S:16][C:17]([C... | CC(N)N1CCN(C)CC(C)(C)SSC(C)(C)CN(C)CC1.NCCN(CCN)CCN | CN(C)CCN1CCN(C)CC(C)(C)SSC(C)(C)CN(C)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | bdbebd3a501ad46082f4f092582a5b21e7e4cc9025deb1b45c60235941322fdd | a21e2cdfdfe89e200a96df013363dac9801b33cd0e2c9f700170af4f1d6e494c | C1CNCCSSCCNCCN1 | N-C-C-[N;H0;D3;+0:1](-[CH2;D2;+0:2]-C-N)-[CH2;D2;+0:3]-C-N.N-[CH;D3;+0:4](-[CH3;D1;+0:5])-[#7:6](-[C:7])-[C:8]>>[C:7]-[#7:6](-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[N;H0;D3;+0:1](-[CH3;D1;+0:2])-[CH3;D1;+0:3])-[C:8] | null | [] | null | null | null | null | 1H NMR (300 MHz,in CDCl3): δ2.71 (t,J=6 Hz,4H,-N-CH2 -CH2 -N(CH3)-), 2.64 (s,4H,-N-CH2 -C(CH3)2-S-), 2.62 (t,J=6 Hz,4H,-N-CH2 -CH2 -N(CH3)-), 2.52 (m,2H,-CH2 -CH2 -N(CH3)2), 2.46 (m,2H,-CH2 -CH2 -N(CH3 (2), 2.37 (s,6H,-CH2 -N(CH3)-CH2 -), 2.25 (s,6H,-CH2 -CH2 -N(CH3)2) and 1.28 (s,12H,-S-C(CH3)2 -) ppm. 13C NMR (75 MHz... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine.Primary amine.Primary amine.Tertiary amine | Tertiary amine | null | null | C1C[NH]CCSSCC[NH]CC[NH]1 | Other | null | null | null | CC(N)N1CCN(C)CC(C)(C)SSC(C)(C)CN(C)CC1.NCCN(CCN)CCN>>CN(C)CCN1CCN(C)CC(C)(C)SSC(C)(C)CN(C)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2102415670e84ba2a1c07b79e8f9c07d | CC(C)(C)OC(=O)N1CCNCC1.CSCC[C@H](NC(C)=O)C(=O)O>>CSCC[C@H](NC(C)=O)C(=O)N1CCN(C(=O)OC(C)(C)C)CC1 | C(C)(C)(C)OC(=O)N1CCNCC1.C1=CC=C2C(=C1)C(=O)C(C2=O)(O)O.II.C1(CCCCC1)N=C=NC1CCCCC1.C(C)(=O)N[C@@H](CCSC)C(=O)O>>C(C)(C)(C)OC(=O)N1CCN(CC1)C([C@@H](NC(C)=O)CCSC)=O | [NH:12]1[CH2:13][CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][CH2:24]1.O[C:10]([C@H:5]([CH2:4][CH2:3][S:2][CH3:1])[NH:6][C:7]([CH3:8])=[O:9])=[O:11]>>[CH3:1][S:2][CH2:3][CH2:4][C@H:5]([NH:6][C:7]([CH3:8])=[O:9])[C:10](=[O:11])[N:12]1[CH2:13][CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([C... | CC(C)(C)OC(=O)N1CCNCC1.CSCC[C@H](NC(C)=O)C(=O)O | CSCC[C@H](NC(C)=O)C(=O)N1CCN(C(=O)OC(C)(C)C)CC1 | null | C(C)(=O)O | ClCCl.C(C)#N.O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ed26ef5eea92a0cc433b3f89a34f4c61724425fa15a9d0ec83a0f7a903eec831 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | C1CNCCN1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8].[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[C:4]-[C:3](-[#7:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[#7:9]-[C:14]-[C:13]-1 | 108.6 | [{"value": 108.6, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C([C@@H](NC(C)=O)CCSC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 4.78 g (0.025 mol) of N-acetyl-L-methionine in CH2C12 : acetonitrile (120 ml) was cooled to 0° C. To this solution was added 5.36 g (0.025 mol) of dicyclohexylcarbodiimide (DCC) followed by the rapid addition of 3.90 g (0.021 mol) of N-t-butoxycarbonylpiperazine in 6 ml of dichloromethane. The progress of... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1 | HO- | C(C)(=O)O.ClCCl.C(C)#N.O1CCCC1 | null | 2 | CC(C)(C)OC(=O)N1CCNCC1.CSCC[C@H](NC(C)=O)C(=O)O>C(C)(=O)O.ClCCl.C(C)#N.O1CCCC1>CSCC[C@H](NC(C)=O)C(=O)N1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d54c7161af5a46979c7c7c4306cad827 | CSCC[C@H](NC(C)=O)C(=O)N1CCN(C(=O)OC(C)(C)C)CC1>>CSCC[C@H](NC(C)=O)C(=O)N1CCNCC1 | C(C)(C)(C)OC(=O)N1CCN(CC1)C([C@@H](NC(C)=O)CCSC)=O.FC(C(=O)O)(F)F>>C(C)(=O)N[C@@H](CCSC)C(=O)N1CCNCC1 | CC(C)(C)OC(=O)[N:15]1[CH2:14][CH2:13][N:12]([C:10]([C@H:5]([CH2:4][CH2:3][S:2][CH3:1])[NH:6][C:7]([CH3:8])=[O:9])=[O:11])[CH2:17][CH2:16]1>>[CH3:1][S:2][CH2:3][CH2:4][C@H:5]([NH:6][C:7]([CH3:8])=[O:9])[C:10](=[O:11])[N:12]1[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]1 | CSCC[C@H](NC(C)=O)C(=O)N1CCN(C(=O)OC(C)(C)C)CC1 | CSCC[C@H](NC(C)=O)C(=O)N1CCNCC1 | null | null | ClCCl | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | C1CNCCN1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | 33.7 | [{"value": 33.7, "product": "C(C)(=O)N[C@@H](CCSC)C(=O)N1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 8.6 g (0.024 mol) of 1-(t-butoxycarbonyl)-4-(N-acetyl-L-methionyl)piperazine in 60 ml of dichloromethane was added 10 ml of trifluoroacetic acid and the mixture was stirred at room temperature overnight. The solution was extracted with water and the resulting aqueous solution was made basic with sodium... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | C1C[NH]CCN1 | HO- | ClCCl | null | 8 | CSCC[C@H](NC(C)=O)C(=O)N1CCN(C(=O)OC(C)(C)C)CC1>ClCCl>CSCC[C@H](NC(C)=O)C(=O)N1CCNCC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e993cca47d064900bb01c95908565f69 | N=C(N)NCCC[C@H](NC(=O)CNC(=O)[C@@H]1CCC(=O)N1)C(=O)Nc1ccc([N+](=O)[O-])cc1>>Nc1ccc([N+](=O)[O-])cc1 | N1[C@@H](CCC1=O)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)NC1=CC=C([N+](=O)[O-])C=C1>>[N+](=O)([O-])C1=CC=C(N)C=C1 | N=C(N)NCCC[C@H](NC(=O)CNC(=O)[C@@H]1CCC(=O)N1)C(=O)[NH:1][c:2]1[cH:3][cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9][cH:10]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9][cH:10]1 | N=C(N)NCCC[C@H](NC(=O)CNC(=O)[C@@H]1CCC(=O)N1)C(=O)Nc1ccc([N+](=O)[O-])cc1 | Nc1ccc([N+](=O)[O-])cc1 | null | null | C(C)(=O)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 5182215259cd859a285a29c22302a81e70eb631af3575fcc1696269f183efe3f | 18cc77a15f8decf44456aa6785fd69cac51884f3c760a636cccdc428190bc1bc | c1ccccc1 | N-C(=N)-N-C-C-C-[C@H](-N-C(=O)-C-N-C(=O)-[C@H]1-C-C-C(=O)-N-1)-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 30 | MINUTE | Next, 50 μl of the synthetic peptide substrate (2 mM), pyroGlu-Gly-Arg-p-nitroanilide (S-2444, Kabi, Sweden) were added and the mixture was incubated for 30 minutes at room temperature. The reaction was stopped by the addition of 1 ml of 10% acetic acid. The amount of p-nitroaniline produced was measured by absorbance ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Secondary amide.Secondary amide.Secondary amide.Primary amine.Secondary amine | Primary amine | C1CCNC1 | null | c1ccccc1 | HO- | C(C)(=O)O | null | 0.5 | N=C(N)NCCC[C@H](NC(=O)CNC(=O)[C@@H]1CCC(=O)N1)C(=O)Nc1ccc([N+](=O)[O-])cc1>C(C)(=O)O>Nc1ccc([N+](=O)[O-])cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-bd8a36d583c74992ace72789377fc73a | COCCOCCOCCOc1cc([N+](=O)[O-])c([N+](=O)[O-])cc1OCCOCCOCCOC>>COCCOCCOCCOc1ccc(N)c(N)c1OCCOCCOCCOC | O.NN.COCCOCCOCCOC1=C(C=C(C(=C1)[N+](=O)[O-])[N+](=O)[O-])OCCOCCOCCOC.C(Cl)Cl.CO>>NC1=C(C(=C(C=C1)OCCOCCOCCOC)OCCOCCOCCOC)N | O=[N+:16]([O-])[c:15]1[c:14]([N+:18](=O)[O-])[cH:13][c:12]([O:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[c:19]([O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH3:30])[cH:17]1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14... | COCCOCCOCCOc1cc([N+](=O)[O-])c([N+](=O)[O-])cc1OCCOCCOCCOC | COCCOCCOCCOc1ccc(N)c(N)c1OCCOCCOCCOC | null | [Pd] | CCO.C(C)O | Functional Group Interconversion | OtherReaction | a81380ceeffc56cd7fa244efd2d9a24abc1b81a5a82add2f012ceea085558fc9 | 86e032c8ebc9cbcd13a880d0d66c541ff63611af16d12657aad958d17abf4587 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2]1:[cH;D2;+0:3]:[c:4](-[#8:5]):[c:6]:[c:7]:[c;H0;D3;+0:8]:1-[N+;H0;D3:9](=O)-[O-]>>[#8:5]-[c:4]1:[c:6]:[c:7]:[cH;D2;+0:8]:[c:2](-[NH2;D1;+0:1]):[c;H0;D3;+0:3]:1-[NH2;D1;+0:9] | 89 | [{"value": 89.0, "product": "NC1=C(C(=C(C=C1)OCCOCCOCCOC)OCCOCCOCCOC)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In an oven dried 500 mL round bottom flask, equipped with a Claisen adapter, pressure equalizing dropping funnel, and reflux condenser, 1,2-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]-4,5-dinitrobenzene 1E (20 g, 0.04 mol) was dissolved in absolute ethanol (200 mL). To this clear solution, 10% palladium on carbon (4 g) wa... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Nitro group | Primary amine.Primary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | [Pd].CCO.C(C)O | null | null | COCCOCCOCCOc1cc([N+](=O)[O-])c([N+](=O)[O-])cc1OCCOCCOCCOC>[Pd].CCO.C(C)O>COCCOCCOCCOc1ccc(N)c(N)c1OCCOCCOCCOC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-fd3f04ce3b4747f998e88ec1d767b13c | OC[C@@H](O)[C@H](O)[C@@H](O)CO>>OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CO | C([O-])([O-])=O.[Ca+2].C([C@H](O)[C@@H](O)[C@H](O)CO)O>>OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO | [OH:1][CH2:2][C@@H:3]([OH:4])[C@H:5]([OH:6])[C@@H:7]([OH:8])[CH2:9][OH:10]>>[OH:1][CH2:2][C@@H:3]([OH:4])[C@@H:5]([OH:6])[C@H:7]([OH:8])[C@@H:9]([OH:10])[CH2:11][OH:12] | OC[C@@H](O)[C@H](O)[C@@H](O)CO | OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CO | null | null | null | Miscellaneous | OtherReaction | bbfa5a4efa40e7a8b5f5a373cb0ead4374bdc2bf34671b8117c68650dca00b27 | c3591f637168801020e6236a976ea21b49baafe37273b6eafe44e2276bb61dcb | null | [C:1]-[C:2](-[O;D1;H1:3])-[CH2;D2;+0:4]-[O;D1;H1:5]>>[C:1]-[C:2](-[O;D1;H1:3])-[C@@H;D3;+0:4](-[O;D1;H1:5])-[C:6]-[O;D1;H1:7] | 22 | [{"value": 22.0, "product": "OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stabilized, substantially non-volatile mixture of 15 grams of a medium chain triglyceride and 22.5 grams of menthol crystals was formed. To this mixture was added 0.45 grams of F, D and C Blue No. 1 H.T. Lake. A second mixture comprising 22.5 grams of polyethylene glycol (8,000 carbowax) with 12 grams of hydrogenated... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary alcohol.Secondary alcohol | null | null | null | Other | null | null | null | OC[C@@H](O)[C@H](O)[C@@H](O)CO>>OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CO |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9001260bcc10489c8c8b22567801e0cf | CC(C)(C)CO.COC(=O)OC>>COC(=O)OCC(C)(C)C | C(C(C)(C)C)O.C(OC)(OC)=O>>C(OC)(OCC(C)(C)C)=O | [OH:5][CH2:6][C:7]([CH3:8])([CH3:9])[CH3:10].CO[C:3]([O:2][CH3:1])=[O:4]>>[CH3:1][O:2][C:3](=[O:4])[O:5][CH2:6][C:7]([CH3:8])([CH3:9])[CH3:10] | CC(C)(C)CO.COC(=O)OC | COC(=O)OCC(C)(C)C | null | C[O-].[Na+].CO | null | Acylation | OtherReaction | 1c06f9a8caae6ebc766646ab74a70a6fc416a5e8df2dc72b023befe5d14528a9 | 772f77da20903ad7c3075e3d8d0f3971a777d13631841b0b2f5034c11a7e5159 | null | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4] | 55 | [{"value": 55.0, "product": "C(OC)(OCC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.0, "product": "C(OC)(OCC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | To a mixed solution of neopentyl alcohol (500 ml, 5.7 mol) and dimethyl carbonate (2070 g, 23.0 mol), a 28% sodium methoxide/methanol solution (11 g) was added and the mixture was heated to 100° C. to remove the methanol by evaporation for 6 hours. After allowing the mixture to cool to room temperature, an aqueous solu... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Primary alcohol | Carbonic Ester | null | null | null | HO- | C[O-].[Na+].CO | 100 | null | CC(C)(C)CO.COC(=O)OC>C[O-].[Na+].CO>COC(=O)OCC(C)(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c04ca43d5701435492ee6ef93800bddf | COC(=O)OC.OCC(F)(F)F>>COC(=O)OCC(F)(F)F | FC(CO)(F)F.C(OC)(OC)=O>>C(OC)(OCC(F)(F)F)=O | CO[C:3]([O:2][CH3:1])=[O:4].[OH:5][CH2:6][C:7]([F:8])([F:9])[F:10]>>[CH3:1][O:2][C:3](=[O:4])[O:5][CH2:6][C:7]([F:8])([F:9])[F:10] | COC(=O)OC.OCC(F)(F)F | COC(=O)OCC(F)(F)F | null | C[O-].[Na+].CO | null | Acylation | OtherReaction | 1c06f9a8caae6ebc766646ab74a70a6fc416a5e8df2dc72b023befe5d14528a9 | 772f77da20903ad7c3075e3d8d0f3971a777d13631841b0b2f5034c11a7e5159 | null | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[F;D1;H0:5]-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[C:9]-[OH;D1;+0:10]>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:10]-[C:9]-[C:6](-[F;D1;H0:5])(-[F;D1;H0:7])-[F;D1;H0:8] | 33 | [{"value": 33.0, "product": "C(OC)(OCC(F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.8, "product": "C(OC)(OCC(F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | In a flask (3-liter volume) equipped with 10 distillation columns, 2,2,2-trifluoroethanol (790 g, 7.9 ml), dimethyl carbonate (2140 g, 23.7 mol) and a 28% sodium methoxide/methanol solution (15.3 g) were charged. The flask was heated to 100° C. to allow the starting materials to react for 30 hours while removing the me... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Primary alcohol | Carbonic Ester | null | null | null | HO- | C[O-].[Na+].CO | 100 | null | COC(=O)OC.OCC(F)(F)F>C[O-].[Na+].CO>COC(=O)OCC(F)(F)F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9eb09862d3164d5ba6ac2ced82dc1dbc | CCOC(=O)Cl.OCC(F)(F)F>>CCOC(=O)OCC(F)(F)F | FC(CO)(F)F.C(OCC)(=O)Cl.[OH-].[K+]>>C(OCC)(OCC(F)(F)F)=O | Cl[C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:6][CH2:7][C:8]([F:9])([F:10])[F:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[O:6][CH2:7][C:8]([F:9])([F:10])[F:11] | CCOC(=O)Cl.OCC(F)(F)F | CCOC(=O)OCC(F)(F)F | null | null | C(C)OCC | Acylation | Schotten-Baumann to ester | ab2604cac7a0887c37303ad0fec59fb6a84cf40820c840730a9f7f5636dcc83e | 7ed0ec8c4c25c8af523f531911c9dd0a60119de4cab841f882ce9a65c39be54c | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[F;D1;H0:5]-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[C:9]-[OH;D1;+0:10]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:10]-[C:9]-[C:6](-[F;D1;H0:5])(-[F;D1;H0:7])-[F;D1;H0:8] | 70 | [{"value": 70.0, "product": "C(OCC)(OCC(F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.7, "product": "C(OCC)(OCC(F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | In a flask (5-liter volume), 2,2,2-trifluoroethanol (800 g, 8.0 mol). ethyl chlorocarbonate (867 g, 8.0 mol) and diethyl ether (1000 ml) were charged. While the flask was cooled so that the reaction was carried out at -5° C. to 0° C., a 29.5% by weight aqueous solution of potassium hydroxide (1500 g) was added dropwise... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary alcohol | Carbonic Ester | null | null | null | HCl | C(C)OCC | null | 12 | CCOC(=O)Cl.OCC(F)(F)F>C(C)OCC>CCOC(=O)OCC(F)(F)F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b1fd55473c5449a3ab3e758cd1fe68cf | COC(=O)OC.OCC(F)(F)C(F)(F)F>>COC(=O)OCC(F)(F)C(F)(F)F | FC(CO)(C(F)(F)F)F.C(OC)(OC)=O>>C(OC)(OCC(C(F)(F)F)(F)F)=O | CO[C:3]([O:2][CH3:1])=[O:4].[OH:5][CH2:6][C:7]([F:8])([F:9])[C:10]([F:11])([F:12])[F:13]>>[CH3:1][O:2][C:3](=[O:4])[O:5][CH2:6][C:7]([F:8])([F:9])[C:10]([F:11])([F:12])[F:13] | COC(=O)OC.OCC(F)(F)C(F)(F)F | COC(=O)OCC(F)(F)C(F)(F)F | null | C[O-].[Na+].CO | null | Acylation | OtherReaction | 1c06f9a8caae6ebc766646ab74a70a6fc416a5e8df2dc72b023befe5d14528a9 | 772f77da20903ad7c3075e3d8d0f3971a777d13631841b0b2f5034c11a7e5159 | null | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4] | 51 | [{"value": 51.0, "product": "C(OC)(OCC(C(F)(F)F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.9, "product": "C(OC)(OCC(C(F)(F)F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | In a flask (500-ml volume) equipped with 10 distillation columns, 2,2,3,3,3-pentafluoropropanol (100 g, 0.67 mol), dimethyl carbonate (180 g, 2.0 mol) and a 28% sodium methoxide/methanol solution (1.3 g) were charged. The flask was heated to 120° C. to allow the starting materials to react for 10 hours while removing t... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Primary alcohol | Carbonic Ester | null | null | null | HO- | C[O-].[Na+].CO | 120 | null | COC(=O)OC.OCC(F)(F)C(F)(F)F>C[O-].[Na+].CO>COC(=O)OCC(F)(F)C(F)(F)F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ba2015bcd1b046308257976504d7a0ba | COC(=O)OC.OCC(F)(F)C(F)F>>COC(=O)OCC(F)(F)C(F)F | FC(CO)(C(F)F)F.C(OC)(OC)=O>>C(OC)(OCC(C(F)F)(F)F)=O | CO[C:3]([O:2][CH3:1])=[O:4].[OH:5][CH2:6][C:7]([F:8])([F:9])[CH:10]([F:11])[F:12]>>[CH3:1][O:2][C:3](=[O:4])[O:5][CH2:6][C:7]([F:8])([F:9])[CH:10]([F:11])[F:12] | COC(=O)OC.OCC(F)(F)C(F)F | COC(=O)OCC(F)(F)C(F)F | null | C[O-].[Na+].CO | null | Acylation | OtherReaction | 1c06f9a8caae6ebc766646ab74a70a6fc416a5e8df2dc72b023befe5d14528a9 | 772f77da20903ad7c3075e3d8d0f3971a777d13631841b0b2f5034c11a7e5159 | null | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4] | 49 | [{"value": 49.0, "product": "C(OC)(OCC(C(F)F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.5, "product": "C(OC)(OCC(C(F)F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | In a flask (500-ml volume) equipped with 10 distillation columns, 2,2,3,3-tetrafluoropropanol (100 g, 0.76 mol), dimethyl carbonate (205 g, 2.3 mol) and a 28% sodium methoxide/methanol solution (1.4 g) were charged. The flask was heated to 120° C. to allow the starting materials to react for 10 hours while removing the... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Primary alcohol | Carbonic Ester | null | null | null | HO- | C[O-].[Na+].CO | 120 | null | COC(=O)OC.OCC(F)(F)C(F)F>C[O-].[Na+].CO>COC(=O)OCC(F)(F)C(F)F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e37be7e79d144758bf50b3682434fb81 | COC(=O)OC.OCC(F)(F)C(F)(F)F>>COC(=O)OCC(F)(F)C(F)(F)F | C(OC)(OC)=O.C(=O)([O-])[O-].[K+].[K+].C[O-].[Na+].CO.FC(CO)(C(F)(F)F)F>>C(OC)(OCC(C(F)(F)F)(F)F)=O | CO[C:3]([O:2][CH3:1])=[O:4].[OH:5][CH2:6][C:7]([F:8])([F:9])[C:10]([F:11])([F:12])[F:13]>>[CH3:1][O:2][C:3](=[O:4])[O:5][CH2:6][C:7]([F:8])([F:9])[C:10]([F:11])([F:12])[F:13] | COC(=O)OC.OCC(F)(F)C(F)(F)F | COC(=O)OCC(F)(F)C(F)(F)F | null | null | null | Acylation | OtherReaction | 1c06f9a8caae6ebc766646ab74a70a6fc416a5e8df2dc72b023befe5d14528a9 | 772f77da20903ad7c3075e3d8d0f3971a777d13631841b0b2f5034c11a7e5159 | null | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4] | 55 | [{"value": 55.0, "product": "C(OC)(OCC(C(F)(F)F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Methyl 2,2,3,3,3-Pentafluoropropyl carbonate was prepared by the same manner as the example 4 except that K2CO3 (0.046 g) was used as a catalyst in stead of a 28% sodium methoxide/methanol solution (1.3 g). After 2,2,3,3,3-pentafluoropropanol and dimethyl carbonate were allowed to react, the mixture thereof was passed ... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Primary alcohol | Carbonic Ester | null | null | null | HO- | null | null | null | COC(=O)OC.OCC(F)(F)C(F)(F)F>>COC(=O)OCC(F)(F)C(F)(F)F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-bce3bb869e764396bc23e7298aa8e4ba | BrBr.Cc1ccc(N)c([N+](=O)[O-])c1>>Cc1cc(Br)c(N)c([N+](=O)[O-])c1 | BrBr.CC1=CC(=C(N)C=C1)[N+](=O)[O-]>>BrC1=C(C(=CC(=C1)C)[N+](=O)[O-])N | Br[Br:5].[CH3:1][c:2]1[cH:3][cH:4][c:6]([NH2:7])[c:8]([N+:9](=[O:10])[O-:11])[cH:12]1>>[CH3:1][c:2]1[cH:3][c:4]([Br:5])[c:6]([NH2:7])[c:8]([N+:9](=[O:10])[O-:11])[cH:12]1 | BrBr.Cc1ccc(N)c([N+](=O)[O-])c1 | Cc1cc(Br)c(N)c([N+](=O)[O-])c1 | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | Br-[Br;H0;D1;+0:1].[N;D1;H2:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:3](-[N;D1;H2:2]):[c:4] | 98.5 | [{"value": 98.0, "product": "BrC1=C(C(=CC(=C1)C)[N+](=O)[O-])N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.5, "product": "BrC1=C(C(=CC(=C1)C)[N+](=O)[O-])N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of bromine (23.24 mL, 453.5 mmol) in glacial acetic acid (50 mL) was added dropwise over 2 h to a mechanically-stirred suspension of 4-methyl-2-nitroaniline (60.00 g, 394.3 mmol) in glacial acetic acid (200 mL) at room temperature under a nitrogen atmosphere. The mixture was stirred at room temperature 1 h, ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | C(C)(=O)O | null | 1 | BrBr.Cc1ccc(N)c([N+](=O)[O-])c1>C(C)(=O)O>Cc1cc(Br)c(N)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-8b376187240b4ed782555b182275be4f | C=C1CC(=O)O1.Cc1cc(Br)c(N)c([N+](=O)[O-])c1>>CC(=O)CC(=O)Nc1c(Br)cc(C)cc1[N+](=O)[O-] | O.O.[Cl-].[Na+].C=C1CC(=O)O1.BrC1=C(C(=CC(=C1)C)[N+](=O)[O-])N>>BrC1=C(C(=CC(=C1)C)[N+](=O)[O-])NC(CC(C)=O)=O | [CH2:1]=[C:2]1[O:3][C:5](=[O:6])[CH2:4]1.[NH2:7][c:8]1[c:9]([Br:10])[cH:11][c:12]([CH3:13])[cH:14][c:15]1[N+:16](=[O:17])[O-:18]>>[CH3:1][C:2](=[O:3])[CH2:4][C:5](=[O:6])[NH:7][c:8]1[c:9]([Br:10])[cH:11][c:12]([CH3:13])[cH:14][c:15]1[N+:16](=[O:17])[O-:18] | C=C1CC(=O)O1.Cc1cc(Br)c(N)c([N+](=O)[O-])c1 | CC(=O)CC(=O)Nc1c(Br)cc(C)cc1[N+](=O)[O-] | null | CN(C1=CC=NC=C1)C | O1CCCC1.ClCCCC | Acylation | OtherReaction | 5b7e5290792b5fd05931d61f1ab4fac4b9a12474dc4c1d1fe9f74041167c288b | 61e32e3b264beb4549f229750ce3ceb3c4831b980f4210ceb397f2f215863ce1 | c1ccccc1 | [CH2;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-1.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[CH3;D1;+0:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:6])-[C:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 46 | [{"value": 46.0, "product": "BrC1=C(C(=CC(=C1)C)[N+](=O)[O-])NC(CC(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.0, "product": "BrC1=C(C(=CC(=C1)C)[N+](=O)[O-])NC(CC(C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of diketene (57.71 mL, 748.2 mmol) was added dropwise over 2 h to a stirred solution of title compound of Step A (34.57 g, 149.6 mmol) and 4-dimethylaminopyridine (914 mg, 7.48 mmol) in dry tetrahydrofuran (450 mL) at room temperature under a nitrogen atmosphere. The reaction was allowed to stir at room temp... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine.Vinyl | Ketone.Secondary amide | C1COC1 | null | c1ccccc1 | null | CN(C1=CC=NC=C1)C.O1CCCC1.ClCCCC | null | 8 | C=C1CC(=O)O1.Cc1cc(Br)c(N)c([N+](=O)[O-])c1>CN(C1=CC=NC=C1)C.O1CCCC1.ClCCCC>CC(=O)CC(=O)Nc1c(Br)cc(C)cc1[N+](=O)[O-] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-961ef8e0d2254aeeb0222653c66e30f3 | CC(=O)CC(=O)Nc1c(Br)cc(C)cc1[N+](=O)[O-]>>Cc1cc(Br)c2nc(O)c[n+]([O-])c2c1 | Cl.Cl.BrC1=C(C(=CC(=C1)C)[N+](=O)[O-])NC(CC(C)=O)=O.[OH-].[Na+]>>BrC=1C=C(C=C2[N+](=CC(=NC12)O)[O-])C | CC(=O)[CH2:10][C:8]([NH:7][c:6]1[c:4]([Br:5])[cH:3][c:2]([CH3:1])[cH:14][c:13]1[N+:11](=O)[O-:12])=[O:9]>>[CH3:1][c:2]1[cH:3][c:4]([Br:5])[c:6]2[n:7][c:8]([OH:9])[cH:10][n+:11]([O-:12])[c:13]2[cH:14]1 | CC(=O)CC(=O)Nc1c(Br)cc(C)cc1[N+](=O)[O-] | Cc1cc(Br)c2nc(O)c[n+]([O-])c2c1 | null | null | O.C(C)(C)O | Aromatic Heterocycle Formation | OtherReaction | dbeaf95e8c60f8a2239be1828f0c77c3d9697c30429f1dca540d88c35e86b191 | b2f32db516037f047521b1073c23b36649646661bfde4f7b72846a5f05afa84a | c1ccc2[nH+]ccnc2c1 | C-C(=O)-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7](-[N+;H0;D3:8](=O)-[O;-;D1;H0:9]):[c:10]>>[O;-;D1;H0:9]-[n+;H0;D3:8]1:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[OH;D1;+0:3]):[n;H0;D2;+0:4]:[c:5](:[c:6]):[c:7]:1:[c:10] | 91.2 | [{"value": 91.0, "product": "BrC=1C=C(C=C2[N+](=CC(=NC12)O)[O-])C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.2, "product": "BrC=1C=C(C=C2[N+](=CC(=NC12)O)[O-])C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | The title compound of Step B (11.75 g, 37.29 mmol) was suspended in a mixture of isopropanol (120 mL) and water (120 mL) at room temperature under a nitrogen atmosphere. A solution of sodium hydroxide (14.91 g of a 50% aqueous solution, 186.4 mmol) diluted with water (10 mL) was added dropwise to the mixture over 30 mi... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Nitro group.Secondary amide | Aromatic alcohol | c1ccccc1 | C1=Nc2ccccc2[NH+]=C1 | C1=Nc2ccccc2[NH+]=C1 | HO- | O.C(C)(C)O | null | 8 | CC(=O)CC(=O)Nc1c(Br)cc(C)cc1[N+](=O)[O-]>O.C(C)(C)O>Cc1cc(Br)c2nc(O)c[n+]([O-])c2c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ac830d54b7724a8b93da7678034827fa | Cc1cc(Br)c2nc(O)c[n+]([O-])c2c1>>Cc1cc(Br)c2nc(O)cnc2c1 | BrC=1C=C(C=C2[N+](=CC(=NC12)O)[O-])C.S(=O)([O-])S(=O)[O-].[Na+].[Na+]>>BrC=1C=C(C=C2N=CC(=NC12)O)C | [O-][n+:11]1[cH:10][c:8]([OH:9])[n:7][c:6]2[c:4]([Br:5])[cH:3][c:2]([CH3:1])[cH:13][c:12]21>>[CH3:1][c:2]1[cH:3][c:4]([Br:5])[c:6]2[n:7][c:8]([OH:9])[cH:10][n:11][c:12]2[cH:13]1 | Cc1cc(Br)c2nc(O)c[n+]([O-])c2c1 | Cc1cc(Br)c2nc(O)cnc2c1 | null | null | O.C(C)O | Functional Group Interconversion | OtherReaction | cba54b73cc7260c4f6c8071e80144f2309a3f0e13da5d87e78a7e26446efb16e | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccc2nccnc2c1 | [O-]-[n+;H0;D3:1]1:[c:2]:[c:3](-[O;D1;H1:4]):[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]>>[O;D1;H1:4]-[c:3]1:[#7;a:5]:[c:6](:[c:7]):[c:8](:[c:9]):[n;H0;D2;+0:1]:[c:2]:1 | 65.3 | [{"value": 65.0, "product": "BrC=1C=C(C=C2N=CC(=NC12)O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.3, "product": "BrC=1C=C(C=C2N=CC(=NC12)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | The title compound of Step C (25 g, 98 mmol) and sodium dithionite (38 g, 220 mmol) were suspended in a mixture of ethanol (1000 mL) and water (200 mL) at room temperature. After 1 h, most of the solvent was removed under reduced pressure. The residue was diluted with water and acidified with hydrochloric acid. Insolub... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=Nc2ccccc2[NH+]=C1 | c1ccc2nccnc2c1 | c1ccc2nccnc2c1 | Other | O.C(C)O | null | 1 | Cc1cc(Br)c2nc(O)c[n+]([O-])c2c1>O.C(C)O>Cc1cc(Br)c2nc(O)cnc2c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-aa24d111c02e4dc5a5481afc71f24fef | Cc1cc(Br)c2nc(O)cnc2c1.FC(F)Cl>>Cc1cc(Br)c2nc(OC(F)F)cnc2c1 | ClC(F)F.O.[OH-].[Na+].BrC=1C=C(C=C2N=CC(=NC12)O)C>>BrC=1C=C(C=C2N=CC(=NC12)OC(F)F)C | [CH3:1][c:2]1[cH:3][c:4]([Br:5])[c:6]2[n:7][c:8]([OH:9])[cH:13][n:14][c:15]2[cH:16]1.Cl[CH:10]([F:11])[F:12]>>[CH3:1][c:2]1[cH:3][c:4]([Br:5])[c:6]2[n:7][c:8]([O:9][CH:10]([F:11])[F:12])[cH:13][n:14][c:15]2[cH:16]1 | Cc1cc(Br)c2nc(O)cnc2c1.FC(F)Cl | Cc1cc(Br)c2nc(OC(F)F)cnc2c1 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | O1CCOCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | f71746b437f06cff8a64ae80ec4989a9ba690dfb75f233569f959f7c1c70ee3d | d674a4e29cb9c6ff02aced7b3a1a65ea0cc2cf9c3c85791f3e260cc78f258f15 | c1ccc2nccnc2c1 | Cl-[CH;D3;+0:1](-[F;D1;H0:2])-[F;D1;H0:3].[OH;D1;+0:4]-[c:5]1:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:[c:10]:1>>[F;D1;H0:2]-[CH;D3;+0:1](-[F;D1;H0:3])-[O;H0;D2;+0:4]-[c:5]1:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:[c:10]:1 | 52 | [{"value": 52.0, "product": "BrC=1C=C(C=C2N=CC(=NC12)OC(F)F)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Tetrabutylammonium bromide (689 mg, 2.14 mmol) and sodium hydroxide (17.1 g of a 50% aqueous solution, 214 mmol) were added to a solution of the title compound of Step D (5.11 g, 21.4 mmol) in dioxane (250 mL) at room temperature. Chlorodifluoromethane was condensed with a cold finger trap and added to the reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide.Secondary halide.Aromatic alcohol | Secondary halide.Secondary halide.Ether | null | null | c1ccc2nccnc2c1 | HCl | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.O1CCOCC1 | null | 8 | Cc1cc(Br)c2nc(O)cnc2c1.FC(F)Cl>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.O1CCOCC1>Cc1cc(Br)c2nc(OC(F)F)cnc2c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f47ceb4b2cb54da08b01b4015880bd80 | FC1(F)Oc2ccccc2O1>>OB(O)c1cccc2c1OC(F)(F)O2 | Cl.Cl.COB(OC)OC.FC1(OC2=C(O1)C=CC=C2)F.[Cl-].[Na+].C(CCC)[Li]>>FC1(OC2=C(O1)C=CC=C2B(O)O)F | [cH:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]1[O:10][C:11]([F:12])([F:13])[O:14]2>>[OH:1][B:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]1[O:10][C:11]([F:12])([F:13])[O:14]2 | FC1(F)Oc2ccccc2O1 | OB(O)c1cccc2c1OC(F)(F)O2 | null | null | O1CCCC1.O | Functional Group Interconversion | OtherReaction | 1949fa8ee88afd1f046f27213d5ee74604a3b3aae43c31b9bf334761fbde0e7a | d6d312d46f766d2774f96de1fd96fd8f98a20e51a20ef3280f850cd6a3c77869 | c1ccc2c(c1)OCO2 | [c:1]:[c:2]:[cH;D2;+0:3]:[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1>>[O;D1;H1:9]-[#5:10](-[O;D1;H1:11])-[c;H0;D3;+0:3](:[c:2]:[c:1]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1 | 50 | [{"value": 50.0, "product": "FC1(OC2=C(O1)C=CC=C2B(O)O)F", "details": "PERCENTYIELD", "is_desired": false}] | -15 | CELSIUS | 0.5 | HOUR | A solution of n-butyllithium (5.57 mL of a 2.5M solution in hexanes, 13.9 mmol) was added to dry tetrahydrofuran (75 mL) at room temperature under a nitrogen atmosphere. The resulting solution was cooled to -15° C. and N,N,N',N'-tetramethylenediamine (2.10 mL, 13.9 mmol) was added dropwise. The reaction was stirred at ... | 10.6084/m9.figshare.5104873.v1 | null | null | Boronic acid | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | null | O1CCCC1.O | -15 | 0.5 | FC1(F)Oc2ccccc2O1>O1CCCC1.O>OB(O)c1cccc2c1OC(F)(F)O2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6bdd1d1e091c4828a49bbd517c400336 | Cc1cc(Br)c2nc(OC(F)F)cnc2c1.OB(O)c1cccc2c1OC(F)(F)O2>>Cc1cc(-c2cccc3c2OC(F)(F)O3)c2nc(OC(F)F)cnc2c1 | C([O-])([O-])=O.[Na+].[Na+].C(C)(=O)OCC.CCCCCC.BrC=1C=C(C=C2N=CC(=NC12)OC(F)F)C.FC1(OC2=C(O1)C=CC=C2B(O)O)F>>FC1(OC2=C(O1)C=CC=C2C=2C=C(C=C1N=CC(=NC21)OC(F)F)C)F | Br[c:4]1[cH:3][c:2]([CH3:1])[cH:26][c:25]2[c:16]1[n:17][c:18]([O:19][CH:20]([F:21])[F:22])[cH:23][n:24]2.OB(O)[c:5]1[cH:6][cH:7][cH:8][c:9]2[c:10]1[O:11][C:12]([F:13])([F:14])[O:15]2>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]3[c:10]2[O:11][C:12]([F:13])([F:14])[O:15]3)[c:16]2[n:17][c:18]([O:19][CH:20]([F:... | Cc1cc(Br)c2nc(OC(F)F)cnc2c1.OB(O)c1cccc2c1OC(F)(F)O2 | Cc1cc(-c2cccc3c2OC(F)(F)O3)c2nc(OC(F)F)cnc2c1 | null | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | O.COCCOC | C-C Coupling | Suzuki coupling with boronic acids | ed9bad7efec3b51d5869944ec4ccf9d532559fc12336e44e56b42cc9b75a0d80 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cc2c(c(-c3cccc4nccnc34)c1)OCO2 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:[c:10]:2:1.O-B(-O)-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]1:[c:15]-[#8:16]-[C:17]-[#8:18]-1>>[c:13]:[c:12]:[c;H0;D3;+0:11](-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:[c:10]:2:1):[c:14]1:[c:15]-[#8:16]-[C:17]-[#8:18]-1 | null | [] | null | null | null | null | To a solution of the title compound of Step E (1.65 g, 5.73 mmol) in ethylene glycol dimethyl ether (25 mL) was added the title compound of Step F (1.73 g, 8.59 mmol), a solution of sodium carbonate (1.82 g, 17.2 mmol) in water (15 mL) and bis(triphenylphosphine) palladium (II) chloride (201 mg, 0.286 mmol). The mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2nccnc2c1.c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2.c1ccc2nccnc2c1 | c1ccc2c(c1)OCO2.c1ccc2nccnc2c1 | HBr.B | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.O.COCCOC | null | null | Cc1cc(Br)c2nc(OC(F)F)cnc2c1.OB(O)c1cccc2c1OC(F)(F)O2>[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.O.COCCOC>Cc1cc(-c2cccc3c2OC(F)(F)O3)c2nc(OC(F)F)cnc2c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-938589f386a14a4bbc484da563c53622 | BrBr.FC1(F)Oc2ccccc2O1>>FC1(F)Oc2ccc(Br)cc2O1 | BrBr.FC1(OC2=C(O1)C=CC=C2)F>>BrC1=CC2=C(OC(O2)(F)F)C=C1 | Br[Br:9].[F:1][C:2]1([F:3])[O:4][c:5]2[cH:6][cH:7][cH:8][cH:10][c:11]2[O:12]1>>[F:1][C:2]1([F:3])[O:4][c:5]2[cH:6][cH:7][c:8]([Br:9])[cH:10][c:11]2[O:12]1 | BrBr.FC1(F)Oc2ccccc2O1 | FC1(F)Oc2ccc(Br)cc2O1 | null | [Fe] | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Bromination | 684aaea30ea96ac3399be761a03275b73ad5093abe190412ef63066807650194 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2c(c1)OCO2 | Br-[Br;H0;D1;+0:1].[#8:2]-[c:3]:[c:4]:[cH;D2;+0:5]:[c:6]:[c:7]>>[#8:2]-[c:3]:[c:4]:[c;H0;D3;+0:5](-[Br;H0;D1;+0:1]):[c:6]:[c:7] | 64.1 | [{"value": 64.0, "product": "BrC1=CC2=C(OC(O2)(F)F)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.1, "product": "BrC1=CC2=C(OC(O2)(F)F)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Iron powder (2.8 g, 50 mmol) was added to a solution of 2,2-difluoro-1,3-benzodioxole (15.8 g, 100 mmol) in carbon tetrachloride (200 mL) at 0° C. under a nitrogen atmosphere. Bromine (5.2 mL, 100 mmol) was then added to the mixture dropwise over 15 min. The reaction was heated to reflux for 1 h and then stirred at roo... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | HBr | [Fe].C(Cl)(Cl)(Cl)Cl | null | 8 | BrBr.FC1(F)Oc2ccccc2O1>[Fe].C(Cl)(Cl)(Cl)Cl>FC1(F)Oc2ccc(Br)cc2O1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-01e142ca746b4a8f92e589c35be32a22 | CC(C)OB(OC(C)C)OC(C)C.FC1(F)Oc2ccc(Br)cc2O1>>OB(O)c1ccc2c(c1)OC(F)(F)O2 | C(C)(C)OB(OC(C)C)OC(C)C.C(CCC)[Li].BrC1=CC2=C(OC(O2)(F)F)C=C1>>FC1(OC2=C(O1)C=CC(=C2)B(O)O)F | CC(C)O[B:2]([O:1]C(C)C)[O:3]C(C)C.Br[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[O:10][C:11]([F:12])([F:13])[O:14]2>>[OH:1][B:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[O:10][C:11]([F:12])([F:13])[O:14]2 | CC(C)OB(OC(C)C)OC(C)C.FC1(F)Oc2ccc(Br)cc2O1 | OB(O)c1ccc2c(c1)OC(F)(F)O2 | null | null | O1CCCC1 | Miscellaneous | Preparation of boronic acids | 4c1114821e211241e128738212de27d454c1817efbb83c07fd28c2b2f3081857 | dafd25fbe01879c365f8c874026e570f49824f4bb82016b29d0c5d21aeb58ca3 | c1ccc2c(c1)OCO2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]-[#8:6].C-C(-C)-O-[B;H0;D3;+0:7](-[O;H0;D2;+0:8]-C(-C)-C)-[O;H0;D2;+0:9]-C(-C)-C>>[#8:6]-[c:5]:[c:4]:[c;H0;D3;+0:1](-[B;H0;D3;+0:7](-[OH;D1;+0:8])-[OH;D1;+0:9]):[c:2]:[c:3] | 117.9 | [{"value": 117.9, "product": "FC1(OC2=C(O1)C=CC(=C2)B(O)O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | A solution of the title compound of Step A (15 g, 63 mmol) in tetrahydrofuran (approximately 200 mL) was cooled to -78° C. under a nitrogen atmosphere. A solution of n-butyllithium (40 mL of a 1.6M solution in hexanes) was added dropwise while maintaining the reaction temperature below -55° C. The reaction mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Boronic acid | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | HBr | O1CCCC1 | null | 5 | CC(C)OB(OC(C)C)OC(C)C.FC1(F)Oc2ccc(Br)cc2O1>O1CCCC1>OB(O)c1ccc2c(c1)OC(F)(F)O2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3059335a2ed14734ab0b8b6bd679db34 | CC(=O)Nc1ccc(C)cc1Br.OB(O)c1ccc2c(c1)OC(F)(F)O2>>CC(=O)Nc1ccc(C)cc1-c1ccc2c(c1)OC(F)(F)O2 | FC1(OC2=C(O1)C=CC(=C2)B(O)O)F.C([O-])([O-])=O.[Na+].[Na+].CC1=CC(=C(C=C1)NC(=O)C)Br.FC1(OC2=C(O1)C=CC(=C2)B(O)O)F.C([O-])([O-])=O.[Na+].[Na+]>>FC1(OC2=C(O1)C=CC(=C2)C2=C(C=CC(=C2)C)NC(C)=O)F | Br[c:11]1[c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:6][cH:7][c:8]([CH3:9])[cH:10]1.OB(O)[c:12]1[cH:13][cH:14][c:15]2[c:16]([cH:17]1)[O:18][C:19]([F:20])([F:21])[O:22]2>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([CH3:9])[cH:10][c:11]1-[c:12]1[cH:13][cH:14][c:15]2[c:16]([cH:17]1)[O:18][C:19]([F:20])([F:21])[O:22]2 | CC(=O)Nc1ccc(C)cc1Br.OB(O)c1ccc2c(c1)OC(F)(F)O2 | CC(=O)Nc1ccc(C)cc1-c1ccc2c(c1)OC(F)(F)O2 | null | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | O.COCCOC | C-C Coupling | Suzuki coupling with boronic acids | 4eaac3524feef0fac9270283493ac343cfbd88f66b23f78df9bf06d23e299fd5 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3c(c2)OCO3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8]):[c:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]-[#8:15]>>[#8:15]-[c:14]:[c:13]:[c;H0;D3;+0:10](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8]):[c:9]):[c:11]:[c:12] | null | [] | null | null | null | null | To a mixture of 2-bromo-4-methylacetanilide (1.5 g, 6.6 mmol) and the title compound of Step B (2.0 g, 9.9 mmol) in ethylene glycol dimethyl ether (20 mL) were added a solution of sodium carbonate (2.1 g, 20 mmol) in water (20 mL) and bis(triphenylphosphine) palladium (II) chloride (230 mg, 0.33 mmol). The mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2c(c1)OCO2 | c1ccccc1.c1ccc2c(c1)OCO2 | c1ccccc1.c1ccc2c(c1)OCO2 | HBr.B | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.O.COCCOC | null | null | CC(=O)Nc1ccc(C)cc1Br.OB(O)c1ccc2c(c1)OC(F)(F)O2>[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.O.COCCOC>CC(=O)Nc1ccc(C)cc1-c1ccc2c(c1)OC(F)(F)O2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d18919271ba346f0943598126ca972e9 | Cc1ccc(NC(=O)C(C)(C)C)c(B(O)O)c1.FC1(F)Oc2cccc(Br)c2O1>>Cc1ccc(NC(=O)C(C)(C)C)c(-c2cccc3c2OC(F)(F)O3)c1 | C(C)(=O)OCC.CCCCCC.B(O)(O)C1=C(C=CC(=C1)C)NC(C(C)(C)C)=O.C([O-])([O-])=O.[Na+].[Na+].BrC1=CC=CC=2OC(OC21)(F)F>>FC1(OC2=C(O1)C=CC=C2C2=C(C=CC(=C2)C)NC(C(C)(C)C)=O)F | OB(O)[c:13]1[c:5]([NH:6][C:7](=[O:8])[C:9]([CH3:10])([CH3:11])[CH3:12])[cH:4][cH:3][c:2]([CH3:1])[cH:25]1.Br[c:14]1[cH:15][cH:16][cH:17][c:18]2[c:19]1[O:20][C:21]([F:22])([F:23])[O:24]2>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[C:9]([CH3:10])([CH3:11])[CH3:12])[c:13](-[c:14]2[cH:15][cH:16][cH:17][c:18]3[c:19]... | Cc1ccc(NC(=O)C(C)(C)C)c(B(O)O)c1.FC1(F)Oc2cccc(Br)c2O1 | Cc1ccc(NC(=O)C(C)(C)C)c(-c2cccc3c2OC(F)(F)O3)c1 | null | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | O.COCCOC | C-C Coupling | Suzuki coupling with boronic acids | 4eaac3524feef0fac9270283493ac343cfbd88f66b23f78df9bf06d23e299fd5 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccc3c2OCO3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1.O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12](-[#7:13]-[C:14]=[O;D1;H0:15]):[c:16]>>[O;D1;H0:15]=[C:14]-[#7:13]-[c:12](:[c:16]):[c;H0;D3;+0:9](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1):[c:10]:[c:11] | null | [] | null | null | null | null | To a mixture of the title compound of Step B (10.0 g, 42.2 mmol) and the title compound of Step A (4.96 g, 21.1 mmol) in ethylene glycol dimethyl ether (100 mL) were added a solution of sodium carbonate (4.47 g, 42.2 mmol) in water (25 mL) and bis(triphenylphosphine) palladium (II) chloride (740 mg, 1.05 mmol) at room ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2c(c1)OCO2 | c1ccccc1.c1ccc2c(c1)OCO2 | c1ccccc1.c1ccc2c(c1)OCO2 | HBr.B | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.O.COCCOC | null | null | Cc1ccc(NC(=O)C(C)(C)C)c(B(O)O)c1.FC1(F)Oc2cccc(Br)c2O1>[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.O.COCCOC>Cc1ccc(NC(=O)C(C)(C)C)c(-c2cccc3c2OC(F)(F)O3)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9130d3fad57549ea933b423cbc358a19 | FC(F)(Br)C(F)(F)Br.FC1(F)Oc2ccccc2OC1(F)F>>FC1(F)Oc2cccc(Br)c2OC1(F)F | BrC(C(Br)(F)F)(F)F.C(CCC)[Li].FC1(C(OC2=C(O1)C=CC=C2)(F)F)F.[Cl-].[Na+]>>BrC1=CC=CC=2OC(C(OC21)(F)F)(F)F | FC(F)(Br)C(F)(F)[Br:10].[F:1][C:2]1([F:3])[O:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:11]2[O:12][C:13]1([F:14])[F:15]>>[F:1][C:2]1([F:3])[O:4][c:5]2[cH:6][cH:7][cH:8][c:9]([Br:10])[c:11]2[O:12][C:13]1([F:14])[F:15] | FC(F)(Br)C(F)(F)Br.FC1(F)Oc2ccccc2OC1(F)F | FC1(F)Oc2cccc(Br)c2OC1(F)F | null | null | O1CCCC1.O | Functional Group Interconversion | Bromination | f73ec388e165bd36cf56b9c8d1e55695fba64178a8b7c568fb122a53aa700f5d | 019ad5fd0dfe62cfb4244afde83961e2345586820445df7561489ed4a5d090fa | c1ccc2c(c1)OCCO2 | Br-C(-F)(-F)-C(-F)(-F)-[Br;H0;D1;+0:1].[#8:2]-[c:3]:[c:4](:[cH;D2;+0:5]:[c:6]:[c:7])-[#8:8]-[C:9]>>[#8:2]-[c:3]:[c:4](:[c;H0;D3;+0:5](-[Br;H0;D1;+0:1]):[c:6]:[c:7])-[#8:8]-[C:9] | null | [] | -78 | CELSIUS | 30 | MINUTE | A solution of 2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin (5.00 g, 24.0 mmol) in dry tetrahydrofuran (150 mL) is cooled to -78° C. under a nitrogen atmosphere. A solution of n-butyllithium (10.6 mL, 26.4 mmol of a 2.5M solution in hexanes) is added dropwise while maintaining the reaction temperature below -65° C. T... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide | Aromatic halide | c1ccc2c(c1)OCCO2 | c1ccc2c(c1)OCCO2 | c1ccc2c(c1)OCCO2 | HF.Br- | O1CCCC1.O | -78 | 0.5 | FC(F)(Br)C(F)(F)Br.FC1(F)Oc2ccccc2OC1(F)F>O1CCCC1.O>FC1(F)Oc2cccc(Br)c2OC1(F)F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-afe96e785cfc4f1c9f88cafef09f3c63 | NS(=O)(=O)c1cc(C(=O)O)c(NCc2ccco2)cc1Cl>>NS(=O)(=O)c1cc(C(=O)O)c(NCc2ccco2)cc1Cl | C=1C=C(OC1)CNC2=CC(=C(C=C2C(=O)O)S(=O)(=O)N)Cl.CC=1C=CC=CC1N2C(NC=3C=C(C(=CC3C2=O)S(=O)(=O)N)Cl)C>>CC=1C=CC=CC1N2C(NC=3C=C(C(=CC3C2=O)S(=O)(=O)N)Cl)C.C=1C=C(OC1)CNC2=CC(=C(C=C2C(=O)O)S(=O)(=O)N)Cl | [NH2:25][S:26](=[O:27])(=[O:28])[c:29]1[cH:30][c:31]([C:32](=[O:33])[OH:34])[c:35]([NH:36][CH2:37][c:38]2[cH:39][cH:40][cH:41][o:42]2)[cH:43][c:44]1[Cl:45]>>[NH2:25][S:26](=[O:27])(=[O:28])[c:29]1[cH:30][c:31]([C:32](=[O:33])[OH:34])[c:35]([NH:36][CH2:37][c:38]2[cH:39][cH:40][cH:41][o:42]2)[cH:43][c:44]1[Cl:45] | NS(=O)(=O)c1cc(C(=O)O)c(NCc2ccco2)cc1Cl | NS(=O)(=O)c1cc(C(=O)O)c(NCc2ccco2)cc1Cl | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(NCc2ccco2)cc1 | null | null | [] | null | null | null | null | Rats (450 g previously untreated) were intraperitoneally administered 0.5 ml of 4 mg/ml lasix solution (4 mg/kg dose) and 0.5 ml of 2 mg/ml metolazone/tris buffer solution, pH 11.5, (2 mg/kg dose). The results are shown in Table V below.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccoc1 | null | null | null | null | NS(=O)(=O)c1cc(C(=O)O)c(NCc2ccco2)cc1Cl>>NS(=O)(=O)c1cc(C(=O)O)c(NCc2ccco2)cc1Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d607fa842ea549ee904a444b8bfe6cd1 | CC(C)C1C=C2CCC3C(C)(C(=O)O)CCCC3(C)C2CC1.CCCCCCCCCCCCCC(=O)OC(C)C.O=C(OCc1ccccc1)c1ccccc1>>CCOc1cc(C=O)ccc1O | C(CCCCCCCCCCCCC)(=O)OC(C)C.CC(C)C1CCC2C(=C1)CCC3C2(CCCC3(C)C(=O)O)C.C(C1=CC=CC=C1)(=O)OCC1=CC=CC=C1>>O=CC1=CC(OCC)=C(O)C=C1 | CC(C)C1C=C2CCC3C(C)(C(=O)O)CCCC3(C)C2[CH2:10][CH2:9]1.CC(C)OC(CCCCCCCCCCC[CH2:2][CH3:1])=[O:8].c1cc[c:11]([CH2:4][O:3][C:7]([c:6]2cccc[cH:5]2)=[O:12])cc1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]=[O:8])[cH:9][cH:10][c:11]1[OH:12] | CC(C)C1C=C2CCC3C(C)(C(=O)O)CCCC3(C)C2CC1.CCCCCCCCCCCCCC(=O)OC(C)C.O=C(OCc1ccccc1)c1ccccc1 | CCOc1cc(C=O)ccc1O | null | null | null | Protection | OtherReaction | 7f2e052feafcd1f221f75489f5cc196697d550bae96a58b5df6b502aa5f03d51 | eca569886a5152743c479a4f3ff4d0ecbc5fe85e41f4704bc74405d908761208 | c1ccccc1 | C-C(-C)-C1-C=C2-C-C-C3-C(-C)(-C-C-C-C-3(-C)-C(-O)=O)-C-2-[CH2;D2;+0:1]-[CH2;D2;+0:2]-1.C-C(-C)-O-C(=[O;H0;D1;+0:3])-C-C-C-C-C-C-C-C-C-C-C-[CH2;D2;+0:4]-[C;D1;H3:5].[O;H0;D1;+0:6]=[C;H0;D3;+0:7](-[O;H0;D2;+0:8]-[CH2;D2;+0:9]-[c;H0;D3;+0:10]1:c:c:c:c:c:1)-[c;H0;D3;+0:11]1:[cH;D2;+0:12]:c:c:c:c:1>>[C;D1;H3:5]-[CH2;D2;+0:4... | null | [] | null | null | null | null | The foregoing formula may require a solubilizing agent, e.g., the methyl ester of dihydroabietic acid (commerical name: HERCOLYN D®), benzyl benzoate, isopropyl myristate and/or C12 -C14 isoparaffin hydrocarbons.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Ester | Aldehyde.Ether.Aromatic alcohol | C1=C2CCC3CCCCC3C2CCC1.c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | null | null | CC(C)C1C=C2CCC3C(C)(C(=O)O)CCCC3(C)C2CC1.CCCCCCCCCCCCCC(=O)OC(C)C.O=C(OCc1ccccc1)c1ccccc1>>CCOc1cc(C=O)ccc1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b975ca7d4b05413b8d2fd1f80e50bdb6 | CC(=O)O.CCC(CC)COC(C(=O)N(C)CC[NH+](C)C)(c1ccccc1)c1ccccc1.NC(CO)(CO)CO>>CN[C@H](CC(=O)O)C(=O)O | S1C(=CC=C1)C1(CCCCC1)N1CCCCC1.CCC(CC)COC(C1=CC=CC=C1)(C2=CC=CC=C2)C(=O)N(C)CC[NH+](C)C.[Cl-].CC(=O)O.C(C(CO)(CO)N)O>>CN[C@H](CC(=O)O)C(=O)O | [CH3:4][C:5](=[O:6])[OH:7].CCC(CC)COC(c1ccccc1)(c1ccccc1)[C:8]([N:2]([CH3:1])[CH2:3]C[NH+](C)C)=[O:9].NC(CO)(CO)C[OH:10]>>[CH3:1][NH:2][C@H:3]([CH2:4][C:5](=[O:6])[OH:7])[C:8](=[O:9])[OH:10] | CC(=O)O.CCC(CC)COC(C(=O)N(C)CC[NH+](C)C)(c1ccccc1)c1ccccc1.NC(CO)(CO)CO | CN[C@H](CC(=O)O)C(=O)O | null | null | null | Acylation | OtherReaction | 888c5838c32bb127332a8288c9576da10f501397ec317cf611e1cbb0cbe611f7 | 9e3a2fda2223094e7dd934741af3937c724d328b4cefc6d48b1c51affb2653fc | null | C-C-C(-C-C)-C-O-C(-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:3](-[C;D1;H3:4])-[CH2;D2;+0:5]-C-[NH+](-C)-C)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.N-C(-C-O)(-C-O)-C-[OH;D1;+0:6].[CH3;D1;+0:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10]>>[C;D1;H3:4]-[NH;D2;+0:3]-[C@H;D3;+0:5](-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10])-[C;H0;D3;+0:1](... | null | [] | null | null | 30 | MINUTE | The effect on the TCP (1-[1-(2-thienyl)-cyclohexyl]piperidine) binding was measured in rat brain synaptic membranes (SPM) prepared as previously described [J. B. Monahan & J. Michel; J. Neurochem. 48:1699-1708 (1987)]. Prior to their use in the binding assay, frozen SPM were thawed, diluted twenty fold with 50 mM Tris/... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Tertiary amide.Primary alcohol.Primary alcohol.Primary alcohol.Primary amine | Carboxylic acid.Secondary amine | c1ccccc1.c1ccccc1 | null | null | HO- | null | null | 0.5 | CC(=O)O.CCC(CC)COC(C(=O)N(C)CC[NH+](C)C)(c1ccccc1)c1ccccc1.NC(CO)(CO)CO>>CN[C@H](CC(=O)O)C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f82ffc1d185d4762a9b078e4e9fabb07 | CCCn1c(=O)c(NC(=O)OC(C)(C)C)nc2ccccc21>>CCCn1c(=O)c(N)nc2ccccc21 | C(CC)N1C(C(=NC2=CC=CC=C12)NC(=O)OC(C)(C)C)=O.[OH-].[Na+]>>C(CC)N1C(C(=NC2=CC=CC=C12)N)=O | CC(C)(C)OC(=O)[NH:8][c:7]1[c:5](=[O:6])[n:4]([CH2:3][CH2:2][CH3:1])[c:15]2[c:10]([n:9]1)[cH:11][cH:12][cH:13][cH:14]2>>[CH3:1][CH2:2][CH2:3][n:4]1[c:5](=[O:6])[c:7]([NH2:8])[n:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]12 | CCCn1c(=O)c(NC(=O)OC(C)(C)C)nc2ccccc21 | CCCn1c(=O)c(N)nc2ccccc21 | null | null | Cl.CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=c1cnc2ccccc2[nH]1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9]>>[C:7]-[#7;a:6]1:[c:5]:[c:4]:[#7;a:3]:[c:2](-[NH2;D1;+0:1]):[c:8]:1=[O;D1;H0:9] | 95.7 | [{"value": 95.0, "product": "C(CC)N1C(C(=NC2=CC=CC=C12)N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.7, "product": "C(CC)N1C(C(=NC2=CC=CC=C12)N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 7.12 grams (0.0234 mol) of carbamate 3 in 50 ml of methanol and 35 ml of 6N hydrochloric acid is stirred at room temperature for 4 hours. The solution is neutralized, with cooling, by addition of 6N sodium hydroxide. The crystals formed are filtered off, washed with water and dried at 50° C. 4.55 g (yield... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2nccnc2c1 | HO- | Cl.CO | null | null | CCCn1c(=O)c(NC(=O)OC(C)(C)C)nc2ccccc21>Cl.CO>CCCn1c(=O)c(N)nc2ccccc21 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-55ff37946a134630811817199fc061c1 | Cl>>Cl | C(CC)N1C(C(=NC2=CC=CC=C12)N)=O.Cl.Cl>>Cl.C(CC)N1C(C(=NC2=CC=CC=C12)N)=O | [ClH:16]>>[ClH:16] | Cl | Cl | null | null | C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 80 | [{"value": 80.0, "product": "Cl.C(CC)N1C(C(=NC2=CC=CC=C12)N)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The crystals of compound 4 obtained above are suspended in ethanol. An ethanolic solution of hydrogen chloride gas is then added: the base dissolves and the hydrochloride then begins to precipitate out. After cooling and dilution with ethyl ether, the crystals are filtered off and then washed with a 50/50 ethanol/ethyl... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)O | null | null | Cl>C(C)O>Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9cc6bb4134da49a8b23b96d1e3d313cd | CC(C)(C)OC(=O)N[C@H](Cc1ccccc1)C(=O)O.CC(C)N1C(=O)C(N)N=C(c2ccccc2)c2ccccc21>>CC(C)N1C(=O)C(NC(=O)[C@H](N)Cc2ccccc2)N=C(c2ccccc2)c2ccccc21 | NC1C(N(C2=C(C(=N1)C1=CC=CC=C1)C=CC=C2)C(C)C)=O.C(CCl)Cl.C=1C=CC2=C(C1)N=NN2O.C(=O)(OC(C)(C)C)N[C@H](CC1=CC=CC=C1)C(=O)O>>N[C@@H](C(=O)NC1N=C(C2=C(N(C1=O)C(C)C)C=CC=C2)C2=CC=CC=C2)CC2=CC=CC=C2 | CC(C)(C)OC(=O)[NH:12][C@@H:11]([C:9](O)=[O:10])[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[CH3:1][CH:2]([CH3:3])[N:4]1[C:5](=[O:6])[CH:7]([NH2:8])[N:20]=[C:21]([c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]21>>[CH3:1][CH:2]([CH3:3])[N:4]1[C:5](=[O:6])[CH:7]([NH:8][C:9](=[... | CC(C)(C)OC(=O)N[C@H](Cc1ccccc1)C(=O)O.CC(C)N1C(=O)C(N)N=C(c2ccccc2)c2ccccc21 | CC(C)N1C(=O)C(NC(=O)[C@H](N)Cc2ccccc2)N=C(c2ccccc2)c2ccccc21 | null | null | C(O)([O-])=O.[Na+].CN(C=O)C.C(C)(=O)OCC | Acylation | OtherReaction | b4c20342f55b434660078663f02be082076e2ff9b9068db91acc0b381022a32e | e525bb030a9f5f4a2fc47bce923bf921a3769ce3300b3fa2600575194671a3f3 | O=C(CCc1ccccc1)NC1N=C(c2ccccc2)c2ccccc2NC1=O | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C;H0;D3;+0:4](-O)=[O;D1;H0:5].[C:6]=[#7:7]-[C:8](-[NH2;D1;+0:9])-[C:10](=[O;D1;H0:11])-[#7:12](-[C:13])-[c:14]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:9]-[C:8](-[#7:7]=[C:6])-[C:10](=[O;D1;H0:11])-[#7:12](-[C:13])-[c:14] | null | [] | null | null | 2 | HOUR | To a stirring solution of (+)-3-amino-2,3-dihydro-1-(2-propyl)-2-oxo-5-phenyl-1H-1,4-benzodiazepine (40.8 g, 139 mmol) in dimethylformamide (140 mL) was added EDC (32.0 g, 167 mmol), HOBT (22.6 g, 167 mmol) and N-BOC-D-phenylalanine (44.3 g, 167 mmol). This was stirred at ambient temperature for 2 h. The reaction was d... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Primary amine.Boc | Secondary amide.Primary amine | null | null | c1ccccc1.c1ccccc1.C1=NCC[NH]c2ccccc21 | HO- | C(O)([O-])=O.[Na+].CN(C=O)C.C(C)(=O)OCC | null | 2 | CC(C)(C)OC(=O)N[C@H](Cc1ccccc1)C(=O)O.CC(C)N1C(=O)C(N)N=C(c2ccccc2)c2ccccc21>C(O)([O-])=O.[Na+].CN(C=O)C.C(C)(=O)OCC>CC(C)N1C(=O)C(NC(=O)[C@H](N)Cc2ccccc2)N=C(c2ccccc2)c2ccccc21 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6d72a2c9c9c844b7b0c5df8ca422b9cd | CC(=O)O.N#Cc1ccc(C(F)(F)F)cc1C(F)(F)F>>O=C(O)Cc1ccc(C(F)(F)F)cc1C(F)(F)F | C(C)(=O)O.FC(C1=C(C#N)C=CC(=C1)C(F)(F)F)(F)F.OS(=O)(=O)O.O>>FC(C1=C(C=CC(=C1)C(F)(F)F)CC(=O)O)(F)F | C[C:2](=[O:1])[OH:3].N#[C:4][c:5]1[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][c:14]1[C:15]([F:16])([F:17])[F:18]>>[O:1]=[C:2]([OH:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][c:14]1[C:15]([F:16])([F:17])[F:18] | CC(=O)O.N#Cc1ccc(C(F)(F)F)cc1C(F)(F)F | O=C(O)Cc1ccc(C(F)(F)F)cc1C(F)(F)F | null | null | null | C-C Coupling | OtherReaction | 90c8dd70249cb7803d1965cca696cfb953e179261cd72d5897d4b9c3ff6c7e49 | bf98e437e9d62c3799b8d22cef6764447a2afd089c21ab8eda0c8ca67dbff6fd | c1ccccc1 | C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;D1;H1:3].N#[C;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[O;D1;H1:3])-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 120 | CELSIUS | null | null | 2,4-Bis(trifluoromethyl)benzonitrile (41.5 mmol, 10.51 g) was taken up in 100 mL acetic acid, 50 mL conc. H2SO4, and 20 mL water. This was heated to 120° C. for 3 h. The reaction was then diluted with 1 L ice water, and extracted with 2×300 mL ethyl acetate. The combined organics were washed with 2×200 mL water, dried ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitrile | Carboxylic acid | null | null | c1ccccc1 | Other | null | 120 | null | CC(=O)O.N#Cc1ccc(C(F)(F)F)cc1C(F)(F)F>>O=C(O)Cc1ccc(C(F)(F)F)cc1C(F)(F)F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-11519b9cfafb4d618293384b8bd77b54 | CCOC(=O)C1(C(=O)OCC)CC(=O)N1Cc1ccc(OC)cc1OC>>CCOC(=O)C1(C(=O)OCC)CC(=O)N1 | COC1=C(CN2C(CC2(C(=O)OCC)C(=O)OCC)=O)C=CC(=C1)OC.S(=O)(=O)([O-])OOS(=O)(=O)[O-].[K+].[K+].P(=O)([O-])([O-])[O-].[K+].[K+].[K+]>>O=C1NC(C1)(C(=O)OCC)C(=O)OCC | COc1ccc(C[N:15]2[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([C:7](=[O:8])[O:9][CH2:10][CH3:11])[CH2:12][C:13]2=[O:14])c(OC)c1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1([C:7](=[O:8])[O:9][CH2:10][CH3:11])[CH2:12][C:13](=[O:14])[NH:15]1 | CCOC(=O)C1(C(=O)OCC)CC(=O)N1Cc1ccc(OC)cc1OC | CCOC(=O)C1(C(=O)OCC)CC(=O)N1 | null | null | C(C)#N.O | Reduction | Hydrogenolysis of tertiary amines | 8c791012540cd00dd8767581876a3a29b74a76f305dd0f134cf7763b6abd9738 | 3efc6c7204ad36a2aa7236338bd7163bfb62d1e33efaad6b000b17910587541b | O=C1CCN1 | C-O-c1:c:c:c(-C-[N;H0;D3;+0:1]2-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-2(-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9])-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13]):c(-O-C):c:1>>[C:13]-[#8:12]-[C:10](=[O;D1;H0:11])-[C:5]1(-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9])-[C:4]-[C:2](=[O;D1;H0:3])-[NH;D2;+0:1]-1 | null | [] | 65 | CELSIUS | 1 | HOUR | 1(b) 17.4 g of diethyl 1-(2,4-dimethoxybenzyl)-2-oxoazetidine-4,4-dicarboxylate (prepared as described above) were dissolved in a mixture of 350 ml of acetonitrile and 350 ml of water. 11.2 g of potassium persulfate and 37.4 g of dibasic potassium phosphate were then added to the resulting solution, and the mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Tertiary amide | Secondary amide | c1ccccc1.C1C[NH]C1 | C1CNC1 | C1CNC1 | HO- | C(C)#N.O | 65 | 1 | CCOC(=O)C1(C(=O)OCC)CC(=O)N1Cc1ccc(OC)cc1OC>C(C)#N.O>CCOC(=O)C1(C(=O)OCC)CC(=O)N1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-70e6a23c877648c4afd2e249917b361d | CCOC(=O)C1(C(=O)OCC)CC(=O)N1>>O=C1CC(C(=O)[O-])(C(=O)[O-])N1.[Na+] | O=C1NC(C1)(C(=O)OCC)C(=O)OCC.[OH-].[Na+]>>O=C1NC(C1)(C(=O)[O-])C(=O)[O-].[Na+].[Na+] | CC[O:7][C:5]([C:4]1([C:8](=[O:9])[O:10]CC)[CH2:3][C:2](=[O:1])[NH:11]1)=[O:6]>>[O:1]=[C:2]1[CH2:3][C:4]([C:5](=[O:6])[O-:7])([C:8](=[O:9])[O-:10])[NH:11]1.[Na+:13] | CCOC(=O)C1(C(=O)OCC)CC(=O)N1 | O=C1CC(C(=O)[O-])(C(=O)[O-])N1.[Na+] | null | null | CO | Functional Group Interconversion | OtherReaction | 3d0c4a15f37850238014ea9cf5b9e777f9dd70f2d2ae5ebb7adda479f489012b | a87e633d4c15ade1dd31860f7c44fc378e0d7a7b518b924ae010ea4c26986bb4 | O=C1CCN1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](-[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-C-C)-[#7:8]>>[#7:8]-[C:4](-[C:5](-[O-;H0;D1:7])=[O;D1;H0:6])-[C:2](-[O-;H0;D1:1])=[O;D1;H0:3] | null | [] | null | null | 1 | DAY | 1(c) 5.72 g of diethyl 2-oxoazetidine-4,4-dicarboxylate (prepared as described above) were dissolved in 25 ml of methanol. 53.2 ml of a 1N aqueous solution of sodium hydroxide were added to the resulting solution, and the mixture was stirred at room temperature for 1 day. At the end of this time, the reaction mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | null | null | null | C1CNC1 | Other | CO | null | 24 | CCOC(=O)C1(C(=O)OCC)CC(=O)N1>CO>O=C1CC(C(=O)[O-])(C(=O)[O-])N1.[Na+] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-26423f372bc140e0bcc0d8076fab50a1 | CCOC(=O)C(N)C(=O)OCC.O=C(Cl)CCBr>>CCOC(=O)C(NC(=O)CCBr)C(=O)OCC | BrCCC(=O)Cl.C(C)N(CC)CC.Cl.NC(C(=O)OCC)C(=O)OCC.O>>BrCCC(=O)NC(C(=O)OCC)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH2:7])[C:13](=[O:14])[O:15][CH2:16][CH3:17].Cl[C:8](=[O:9])[CH2:10][CH2:11][Br:12]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][C:8](=[O:9])[CH2:10][CH2:11][Br:12])[C:13](=[O:14])[O:15][CH2:16][CH3:17] | CCOC(=O)C(N)C(=O)OCC.O=C(Cl)CCBr | CCOC(=O)C(NC(=O)CCBr)C(=O)OCC | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C:9](-[NH2;D1;+0:10])-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[C:9](-[C:7](=[O;D1;H0:8])-[#8:6]-[C:5])-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14] | 80.9 | [{"value": 80.9, "product": "BrCCC(=O)NC(C(=O)OCC)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 2(a) 2.8 ml of triethylamine were added to a suspension of 2.11 g of diethyl 2-aminomalonate hydrochloride in 50 ml of methylene chloride. 1.71 g of 3-bromopropionyl chloride were then added to the mixture, whilst ice-cooling, and then the mixture was stirred for 30 minutes. At the end of this time, the reaction mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | null | HCl | C(Cl)Cl | null | 0.5 | CCOC(=O)C(N)C(=O)OCC.O=C(Cl)CCBr>C(Cl)Cl>CCOC(=O)C(NC(=O)CCBr)C(=O)OCC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-18dc032fadb74d58b47edbd36e5bffb9 | CCOC(=O)C(NC(=O)CCBr)C(=O)OCC>>CCOC(=O)C1(C(=O)OCC)CCC(=O)N1 | CCCCCCC=CCCC.BrCCC(=O)NC(C(=O)OCC)C(=O)OCC>>O=C1NC(CC1)(C(=O)OCC)C(=O)OCC | Br[CH2:12][CH2:13][C:14](=[O:15])[NH:16][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:7](=[O:8])[O:9][CH2:10][CH3:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1([C:7](=[O:8])[O:9][CH2:10][CH3:11])[CH2:12][CH2:13][C:14](=[O:15])[NH:16]1 | CCOC(=O)C(NC(=O)CCBr)C(=O)OCC | CCOC(=O)C1(C(=O)OCC)CCC(=O)N1 | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 2ec746c87117cf125fab2602e6958ce66a61fbb749cf3674123a8cc74714adcc | 098246e03ca5d64cc349e355265e564e498af79e5bd90f15ba92540c1f7ceed4 | O=C1CCCN1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[CH;D3;+0:6](-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10])-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14]>>[C:14]-[#8:13]-[C:11](=[O;D1;H0:12])-[C;H0;D4;+0:6]1(-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10])-[#7:5]-[C:3](=[O;D1;H0:4])-[C:2]-[CH2;D2;+0:1]-1 | 37.3 | [{"value": 37.3, "product": "O=C1NC(CC1)(C(=O)OCC)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 2(b) 314 μl of 1,8-diaza[5.4.0]-7-undecene were added to a solution of 620 mg of diethyl 2-(3-bromopropionamido)malonate (prepared as described above) dissolved in methylene chloride, and the mixture was stirred at room temperature for 3 hours. At the end of this time, the reaction mixture was concentrated by evaporati... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester | Ester.Ester | null | C1CCNC1 | C1CCNC1 | HBr | C(Cl)Cl | null | 3 | CCOC(=O)C(NC(=O)CCBr)C(=O)OCC>C(Cl)Cl>CCOC(=O)C1(C(=O)OCC)CCC(=O)N1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6b01a25f8be14edba4c5faad2b8765a1 | CCOC(=O)C1(C(=O)OCC)CCC(=O)N1>>O=C1CCC(C(=O)[O-])(C(=O)[O-])N1.[Na+] | [OH-].[Na+].O=C1NC(CC1)(C(=O)OCC)C(=O)OCC>>O=C1NC(CC1)(C(=O)[O-])C(=O)[O-].[Na+].[Na+] | CC[O:8][C:6]([C:5]1([C:9](=[O:10])[O:11]CC)[CH2:4][CH2:3][C:2](=[O:1])[NH:12]1)=[O:7]>>[O:1]=[C:2]1[CH2:3][CH2:4][C:5]([C:6](=[O:7])[O-:8])([C:9](=[O:10])[O-:11])[NH:12]1.[Na+:14] | CCOC(=O)C1(C(=O)OCC)CCC(=O)N1 | O=C1CCC(C(=O)[O-])(C(=O)[O-])N1.[Na+] | null | null | C(C)O | Functional Group Interconversion | OtherReaction | 3d0c4a15f37850238014ea9cf5b9e777f9dd70f2d2ae5ebb7adda479f489012b | a87e633d4c15ade1dd31860f7c44fc378e0d7a7b518b924ae010ea4c26986bb4 | O=C1CCCN1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](-[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-C-C)-[#7:8]>>[#7:8]-[C:4](-[C:5](-[O-;H0;D1:7])=[O;D1;H0:6])-[C:2](-[O-;H0;D1:1])=[O;D1;H0:3] | null | [] | null | null | 3 | DAY | 2(c) 8.74 ml of a 1N aqueous solution of sodium hydroxide were added to a solution of 1.0 g of diethyl 2-oxopyrrolidine-5,5-dicarboxylate (prepared as described above) in 10 ml of ethanol, and the mixture was stirred at room temperature for 3 days. At the end of this time, the solvent was removed by distillation under ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | null | null | null | C1CCNC1 | Other | C(C)O | null | 72 | CCOC(=O)C1(C(=O)OCC)CCC(=O)N1>C(C)O>O=C1CCC(C(=O)[O-])(C(=O)[O-])N1.[Na+] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-8665e4e9ba584e848afe9d8abb3d246a | COc1ccc(CN2C(=O)C([C@@H](C)O)C2C(=O)OCc2ccccc2)c(OC)c1>>C[C@@H](O)C1C(=O)NC1C(=O)OCc1ccccc1 | COC1=C(CN2C(C(C2C(=O)OCC2=CC=CC=C2)[C@@H](C)O)=O)C=CC(=C1)OC.S(=O)(=O)([O-])OOS(=O)(=O)[O-].[K+].[K+].P(=O)([O-])([O-])[O-].[K+].[K+].[K+]>>O[C@H](C)C1C(NC1C(=O)OCC1=CC=CC=C1)=O | COc1ccc(C[N:7]2[C:5](=[O:6])[CH:4]([C@@H:2]([CH3:1])[OH:3])[CH:8]2[C:9](=[O:10])[O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)c(OC)c1>>[CH3:1][C@@H:2]([OH:3])[CH:4]1[C:5](=[O:6])[NH:7][CH:8]1[C:9](=[O:10])[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | COc1ccc(CN2C(=O)C([C@@H](C)O)C2C(=O)OCc2ccccc2)c(OC)c1 | C[C@@H](O)C1C(=O)NC1C(=O)OCc1ccccc1 | null | null | C(C)#N.O | Reduction | Hydrogenolysis of tertiary amines | 8c791012540cd00dd8767581876a3a29b74a76f305dd0f134cf7763b6abd9738 | 3efc6c7204ad36a2aa7236338bd7163bfb62d1e33efaad6b000b17910587541b | O=C1CC(C(=O)OCc2ccccc2)N1 | C-O-c1:c:c:c(-C-[N;H0;D3;+0:1]2-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-2-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9]):c(-O-C):c:1>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[C:5]1-[C:4]-[C:2](=[O;D1;H0:3])-[NH;D2;+0:1]-1 | null | [] | 70 | CELSIUS | 60 | MINUTE | 3(a) 14 g of benzyl 1-(2,4-dimethoxybenzyl)-3-[(R)-1-hydroxyethyl]-2-oxoazetidine-4-carboxylate [which had been synthesized according to a procedure similar to that described in Tetrahedron 46, 1795 (1984)] were dissolved in a mixture of 420 ml of acetonitrile and 420 ml of water. 66.1 g of potassium persulfate and 23.... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Tertiary amide | Secondary amide | c1ccccc1.C1C[NH]C1 | C1CNC1 | C1CNC1.c1ccccc1 | HO- | C(C)#N.O | 70 | 1 | COc1ccc(CN2C(=O)C([C@@H](C)O)C2C(=O)OCc2ccccc2)c(OC)c1>C(C)#N.O>C[C@@H](O)C1C(=O)NC1C(=O)OCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-889bb27b57964e04bf32c3b369fdcdbb | C[C@@H](O)C1C(=O)NC1C(=O)OCc1ccccc1>>C[C@@H](O)C1C(=O)NC1C(=O)O | O[C@H](C)C1C(NC1C(=O)OCC1=CC=CC=C1)=O>>O[C@H](C)C1C(NC1C(=O)O)=O | c1ccc(C[O:11][C:9]([CH:8]2[CH:4]([C@@H:2]([CH3:1])[OH:3])[C:5](=[O:6])[NH:7]2)=[O:10])cc1>>[CH3:1][C@@H:2]([OH:3])[CH:4]1[C:5](=[O:6])[NH:7][CH:8]1[C:9](=[O:10])[OH:11] | C[C@@H](O)C1C(=O)NC1C(=O)OCc1ccccc1 | C[C@@H](O)C1C(=O)NC1C(=O)O | null | [Pd] | CO | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1CCN1 | [#7:1]-[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-C-c1:c:c:c:c:c:1>>[#7:1]-[C:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5] | null | [] | null | null | null | null | 3(b) 500 mg of the benzyl 3-[(R)-1-hydroxyethyl]-2-oxoazetidine-4-carboxylate (prepared as described in above) were dissolved in 5 ml of methanol, and the mixture was hydrogenated in the presence of 100 mg of a 10% w/w palladium-on-carbon catalyst at room temperature for 2 hours. At the end of this time, the catalyst w... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | C1CNC1 | Other | [Pd].CO | null | null | C[C@@H](O)C1C(=O)NC1C(=O)OCc1ccccc1>[Pd].CO>C[C@@H](O)C1C(=O)NC1C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7adcf7d8bf834507a9a5cff0f9c64b36 | COC(=O)CCCCCCCCO[C@H]1O[C@H](CO)[C@@H](O)[C@H](OC(C)=O)[C@H]1O[C@H]1O[C@H](COC(C)=O)[C@@H](OCc2ccccc2)[C@H](OCc2ccccc2)[C@H]1OCc1ccccc1.CS(=O)(=O)[O-]>>COC(=O)CCCCCCCCO[C@H]1O[C@H](COS(C)(=O)=O)[C@@H](O)[C@H](OC(C)=O)[C@H]1O[C@H]1O[C@H](COC(C)=O)[C@@H](OCc2ccccc2)[C@H](OCc2ccccc2)[C@H]1OCc1ccccc1 | C(C)(=O)O[C@@H]1[C@H]([C@@H](OCCCCCCCCC(=O)OC)O[C@@H]([C@H]1O)CO)O[C@@H]1[C@H](OCC2=CC=CC=C2)[C@@H](OCC2=CC=CC=C2)[C@H](OCC2=CC=CC=C2)[C@H](O1)COC(C)=O.S(C)(=O)(=O)[O-]>>C(C)(=O)O[C@@H]1[C@H]([C@@H](OCCCCCCCCC(=O)OC)O[C@@H]([C@H]1O)COS(=O)(=O)C)O[C@@H]1[C@H](OCC2=CC=CC=C2)[C@@H](OCC2=CC=CC=C2)[C@H](OCC2=CC=CC=C2)[C@H](... | [CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C@H:14]1[O:15][C@H:16]([CH2:17][OH:18])[C@@H:23]([OH:24])[C@H:25]([O:26][C:27]([CH3:28])=[O:29])[C@H:30]1[O:31][C@H:32]1[O:33][C@H:34]([CH2:35][O:36][C:37]([CH3:38])=[O:39])[C@@H:40]([O:41][CH2:42][c:43]2[cH:44][cH:45][cH:46][cH:... | COC(=O)CCCCCCCCO[C@H]1O[C@H](CO)[C@@H](O)[C@H](OC(C)=O)[C@H]1O[C@H]1O[C@H](COC(C)=O)[C@@H](OCc2ccccc2)[C@H](OCc2ccccc2)[C@H]1OCc1ccccc1.CS(=O)(=O)[O-] | COC(=O)CCCCCCCCO[C@H]1O[C@H](COS(C)(=O)=O)[C@@H](O)[C@H](OC(C)=O)[C@H]1O[C@H]1O[C@H](COC(C)=O)[C@@H](OCc2ccccc2)[C@H](OCc2ccccc2)[C@H]1OCc1ccccc1 | null | null | null | Miscellaneous | OtherReaction | 9b60953d4bd7396689a9f1dc793198144ad18c5d1bb07ec2a5c21f6f4e815117 | 6781433991701ad30841681becf17666e4fcc081fce02f6b9b131a47f9893572 | c1ccc(CO[C@@H]2[C@@H](OCc3ccccc3)[C@@H](O[C@@H]3CCCOC3)OC[C@H]2OCc2ccccc2)cc1 | [#8:1]-[C:2]-[C:3]-[OH;D1;+0:4].[C;D1;H3:5]-[S;H0;D4;+0:6](-[O-])(=[O;D1;H0:7])=[O;D1;H0:8]>>[#8:1]-[C:2]-[C:3]-[O;H0;D2;+0:4]-[S;H0;D4;+0:6](-[C;D1;H3:5])(=[O;D1;H0:7])=[O;D1;H0:8] | 85.3 | [{"value": 85.3, "product": "C(C)(=O)O[C@@H]1[C@H]([C@@H](OCCCCCCCCC(=O)OC)O[C@@H]([C@H]1O)COS(=O)(=O)C)O[C@@H]1[C@H](OCC2=CC=CC=C2)[C@@H](OCC2=CC=CC=C2)[C@H](OCC2=CC=CC=C2)[C@H](O1)COC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Compound 24 (570 mg, 0.66 mmol) was converted into its methane sulfonyl derivative exactly as described for the preparation of 10 to give 25 (530 mg, 85.3%) as a syrup after chromatography on silica gel using (hexane:ethyl acetate; 3:2) as eluant; [α]D +76.6° (c 0.57, chloroform). 1H-n.m.r. (CDCl3): δ5.19(t, 1H, J2,3 =... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonic acid | Mesylate | null | null | C1CCOCC1.C1CCOCC1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | COC(=O)CCCCCCCCO[C@H]1O[C@H](CO)[C@@H](O)[C@H](OC(C)=O)[C@H]1O[C@H]1O[C@H](COC(C)=O)[C@@H](OCc2ccccc2)[C@H](OCc2ccccc2)[C@H]1OCc1ccccc1.CS(=O)(=O)[O-]>>COC(=O)CCCCCCCCO[C@H]1O[C@H](COS(C)(=O)=O)[C@@H](O)[C@H](OC(C)=O)[C@H]1O[C@H]1O[C@H](COC(C)=O)[C@@H](OCc2ccccc2)[C@H](OCc2ccccc2)[C@H]1OCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-32ce6edd6bef4c65ac649d1e55c8191a | CC(=O)OC(=S)[C@H]1OC(OC(C)=O)[C@H](OC(C)=O)[C@@H](Oc2ccccc2)[C@@H]1OC(C)=O>>CC(=O)OC[C@H]1OC(O)[C@H](OC(C)=O)C[C@@H]1OC(C)=O | C(C)(=O)OC1[C@H](OC(C)=O)[C@@H](OC2=CC=CC=C2)[C@H](OC(C)=O)[C@H](O1)C(OC(C)=O)=S.C(CCC)[SnH](CCCC)CCCC>>C(C)(=O)O[C@H]1C(O)O[C@@H]([C@H](C1)OC(C)=O)COC(C)=O | CC(=O)[O:9][CH:8]1[O:7][C@H:6]([C:5](=S)[O:4][C:2]([CH3:1])=[O:3])[C@@H:16]([O:17][C:18]([CH3:19])=[O:20])[C@H:15](Oc2ccccc2)[C@H:10]1[O:11][C:12]([CH3:13])=[O:14]>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][C@H:6]1[O:7][CH:8]([OH:9])[C@H:10]([O:11][C:12]([CH3:13])=[O:14])[CH2:15][C@@H:16]1[O:17][C:18]([CH3:19])=[O:20] | CC(=O)OC(=S)[C@H]1OC(OC(C)=O)[C@H](OC(C)=O)[C@@H](Oc2ccccc2)[C@@H]1OC(C)=O | CC(=O)OC[C@H]1OC(O)[C@H](OC(C)=O)C[C@@H]1OC(C)=O | null | null | C1(=CC=CC=C1)C | Reduction | OtherReaction | e4c14ae768ba989e274e1a52463331917b5a935962ecdffbab8769677a602a4d | e38ee42d3bef3956d2e46682a5b1af084766167f26179fd053e6bb57e8e6ca46 | C1CCOCC1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]1-[#8:3]-[C:4](-[C;H0;D3;+0:5](=S)-[#8:6]-[C:7](-[C;D1;H3:8])=[O;D1;H0:9])-[C:10](-[#8:11]-[C:12](-[C;D1;H3:13])=[O;D1;H0:14])-[C@H;D3;+0:15](-O-c2:c:c:c:c:c:2)-[C:16]-1-[#8:17]-[C:18](-[C;D1;H3:19])=[O;D1;H0:20]>>[C;D1;H3:19]-[C:18](=[O;D1;H0:20])-[#8:17]-[C:16]1-[CH2;D2;+0:15]-[C:10](-[#8:... | 135.5 | [{"value": 135.5, "product": "C(C)(=O)O[C@H]1C(O)O[C@@H]([C@H](C1)OC(C)=O)COC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | 1,2,4,6-tetra-O-acetyl-3-O-phenylthiono-glucopyranose (5.2 g) was dissolved in toluene (50 mL) and added to tributyl tin hydride (6.7 mL) and azobisisobutryonitrile (2.8 g). The reaction mixture was heated for 1 to 3 hours at 80° C. to provide for 3-deoxy-2,4,6-tri-O-acetyl-glucopyranose (4.5 g).
Conditions: See reacti... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ether.Thiocarbonyl | Ester.Secondary alcohol | C1CCOCC1.c1ccccc1 | C1CCOCC1 | C1CCOCC1 | Other | C1(=CC=CC=C1)C | 80 | null | CC(=O)OC(=S)[C@H]1OC(OC(C)=O)[C@H](OC(C)=O)[C@@H](Oc2ccccc2)[C@@H]1OC(C)=O>C1(=CC=CC=C1)C>CC(=O)OC[C@H]1OC(O)[C@H](OC(C)=O)C[C@@H]1OC(C)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-cd7c12114e984514b8d82b35efd01ccd | O=C(Br)C(=O)Br.OC1O[C@H](COCc2ccccc2)[C@@H](OCc2ccccc2)C[C@H]1OCc1ccccc1>>BrC1O[C@H](COCc2ccccc2)[C@@H](OCc2ccccc2)C[C@H]1OCc1ccccc1 | C(C1=CC=CC=C1)O[C@H]1C(O)O[C@@H]([C@H](C1)OCC1=CC=CC=C1)COCC1=CC=CC=C1.CN(C)C=O.C(C(=O)Br)(=O)Br>>C(C1=CC=CC=C1)O[C@H]1C(O[C@@H]([C@H](C1)OCC1=CC=CC=C1)COCC1=CC=CC=C1)Br | O=C(Br)C(=O)[Br:1].O[CH:2]1[O:3][C@H:4]([CH2:5][O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[C@@H:14]([O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:23][C@H:24]1[O:25][CH2:26][c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1>>[Br:1][CH:2]1[O:3][C@H:4]([CH2:5][O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:... | O=C(Br)C(=O)Br.OC1O[C@H](COCc2ccccc2)[C@@H](OCc2ccccc2)C[C@H]1OCc1ccccc1 | BrC1O[C@H](COCc2ccccc2)[C@@H](OCc2ccccc2)C[C@H]1OCc1ccccc1 | null | null | ClCCl | Functional Group Interconversion | OtherReaction | edbe343abcae191e59a8b7c8d1ed8c10f6e52652fcab71eb134001accb9f05b8 | b09ce277dcd602b68e9920bcb9affbc52d538599ca7a759ab36af492014f302b | c1ccc(COC[C@H]2OC[C@H](OCc3ccccc3)C[C@@H]2OCc2ccccc2)cc1 | Br-C(=O)-C(=O)-[Br;H0;D1;+0:1].O-[CH;D3;+0:2](-[#8:3]-[C:4])-[C:5](-[#8:6])-[C:7]>>[#8:6]-[C:5](-[C:7])-[CH;D3;+0:2](-[Br;H0;D1;+0:1])-[#8:3]-[C:4] | null | [] | 0 | CELSIUS | 1 | HOUR | 3-Deoxy-2,4,6-tri-O-benzyl-glucopyranose (2.2 g) was dissolved in dichloromethane (20 mL) and dry DMF (880 μL) was added. The reaction solution was cooled at 0° C. and oxalyl bromide (500 μL) was added and the resulting solution stirred at 0° to 5° C. for 1 hour. The solution was then diluted with dichloromethane (100 ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Ether.Secondary alcohol | Secondary halide | C1CCOCC1 | C1CCOCC1 | C1CCOCC1.c1ccccc1.c1ccccc1.c1ccccc1 | HBr | ClCCl | 0 | 1 | O=C(Br)C(=O)Br.OC1O[C@H](COCc2ccccc2)[C@@H](OCc2ccccc2)C[C@H]1OCc1ccccc1>ClCCl>BrC1O[C@H](COCc2ccccc2)[C@@H](OCc2ccccc2)C[C@H]1OCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0dea9024bb7d4473a312fe7ad7811c1f | CCN(CC)CC.CO[C@H]1[C@H](O)[C@@H](CO)OC(O)[C@@H]1O>>C=CCC1(O)O[C@H](CO)[C@@H](O)[C@H](OC)[C@H]1O | C(C)N(CC)CC.CO[C@@H]1[C@H](C(O)O[C@@H]([C@H]1O)CO)O.FC(S(=O)(=O)O)(F)F>>C(C=C)C1(O)[C@H](O)[C@@H](OC)[C@H](O)[C@H](O1)CO | CCN([CH2:1]C)[CH2:3][CH3:2].[CH:4]1([OH:5])[O:6][C@H:7]([CH2:8][OH:9])[C@@H:10]([OH:11])[C@H:12]([O:13][CH3:14])[C@H:15]1[OH:16]>>[CH2:1]=[CH:2][CH2:3][C:4]1([OH:5])[O:6][C@H:7]([CH2:8][OH:9])[C@@H:10]([OH:11])[C@H:12]([O:13][CH3:14])[C@H:15]1[OH:16] | CCN(CC)CC.CO[C@H]1[C@H](O)[C@@H](CO)OC(O)[C@@H]1O | C=CCC1(O)O[C@H](CO)[C@@H](O)[C@H](OC)[C@H]1O | null | null | C(C=C)O.FC(C(=O)O)(F)F | C-C Coupling | OtherReaction | 6411d57862789c812f7a1e2785e0e32bdd5bdb9657491692cae890b673e328d5 | da4b0d2a54a1e8bc31f063d4fb50b426f270269b4ed22f20855284531e33528e | C1CCOCC1 | C-C-N(-[CH2;D2;+0:1]-C)-[CH2;D2;+0:2]-[CH3;D1;+0:3].[C:4]-[C:5](-[O;D1;H1:6])-[CH;D3;+0:7](-[O;D1;H1:8])-[#8:9]-[C:10]>>[C:4]-[C:5](-[O;D1;H1:6])-[C;H0;D4;+0:7](-[O;D1;H1:8])(-[CH2;D2;+0:2]-[CH;D2;+0:3]=[CH2;D1;+0:1])-[#8:9]-[C:10] | 50.8 | [{"value": 50.8, "product": "C(C=C)C1(O)[C@H](O)[C@@H](OC)[C@H](O)[C@H](O1)CO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 3-O-methyl-1,2:5,6-di-O-isopropylidine-glucopyranose (10.2 g) was dissolved in 90% aqueous trifluoroacetic acid (30 mL) and stirred for 1 hour at room temperature. The reaction mixture was evaporated and then coevaporated with toluene followed by ethanol coevaporation to provide the product which was directly used for ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary alcohol.Tertiary amine | Ether.Tertiary alcohol.Allyl | C1CCOCC1 | C1CCOCC1 | C1CCOCC1 | Other | C(C=C)O.FC(C(=O)O)(F)F | null | 1 | CCN(CC)CC.CO[C@H]1[C@H](O)[C@@H](CO)OC(O)[C@@H]1O>C(C=C)O.FC(C(=O)O)(F)F>C=CCC1(O)O[C@H](CO)[C@@H](O)[C@H](OC)[C@H]1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a11503481bb24752a1c157037dda3427 | BrCc1ccccc1.C=CCC1(O)O[C@H](CO)[C@@H](O)[C@H](OC)[C@H]1O>>C=CCC1(O)O[C@H](COCc2ccccc2)[C@@H](OCc2ccccc2)[C@H](OC)[C@H]1OCc1ccccc1 | C(C=C)C1(O)[C@H](O)[C@@H](OC)[C@H](O)[C@H](O1)CO.[H-].[Na+].C(C1=CC=CC=C1)Br>>C(C=C)C1(O)[C@H](OCC2=CC=CC=C2)[C@@H](OC)[C@H](OCC2=CC=CC=C2)[C@H](O1)COCC1=CC=CC=C1 | Br[CH2:31][c:32]1[cH:33][cH:34][cH:35][cH:10][cH:37]1.[CH2:1]=[CH:2][CH2:3][C:4]1([OH:5])[O:6][C@H:7]([CH2:8][OH:9])[C@@H:17]([OH:18])[C@H:26]([O:27][CH3:28])[C@H:29]1[OH:30]>>[CH2:1]=[CH:2][CH2:3][C:4]1([OH:5])[O:6][C@H:7]([CH2:8][O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[C@@H:17]([O:18][CH2:19][c:20]2[... | BrCc1ccccc1.C=CCC1(O)O[C@H](CO)[C@@H](O)[C@H](OC)[C@H]1O | C=CCC1(O)O[C@H](COCc2ccccc2)[C@@H](OCc2ccccc2)[C@H](OC)[C@H]1OCc1ccccc1 | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 77fc7189ae8b9a1747b71995b4422540da77d8a96ff834be19fa984e1ea2fe27 | b8301bbfbb4611baf6a091c5acabb0fbec33741ec27caf76ebcaa8bffeedfb2b | c1ccc(COC[C@H]2OC[C@H](OCc3ccccc3)C[C@@H]2OCc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:1.[OH;D1;+0:8]-[C:9]1-[C:10]-[C:11](-[OH;D1;+0:12])-[C:13]-[#8:14]-[C:15]-1-[C:16]-[OH;D1;+0:17]>>[c:18]:[c:19](-[CH2;D2;+0:6]-[O;H0;D2;+0:17]-[C:16]-[C:15]1-[#8:14]-[C:13]-[C:11](-[O;H0;D2;+0:12]-[CH2;D2;+0:1]-[c:2]2:[c:3]:[c:4]:[cH;D2;+0:5]:[c... | null | [] | 0 | CELSIUS | 0.5 | HOUR | Allyl-3-O-methyl-glucopyranose (4.5 g) was dissolved in anhydrous DMF (120 mL) and sodium hydride (1.84 g, 50% dispersion in oil) was added thereto. The resulting solution was stirred for 0.5 hours at 0° C. Benzyl bromide (6.8 mL) was added dropwise at 0° to 5° C. and the reaction mixture was then stirred for 4 hours a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol.Secondary alcohol.Secondary alcohol | Ether.Ether.Ether | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | C1CCOCC1.c1ccccc1.c1ccccc1.c1ccccc1 | Br- | CN(C)C=O | 0 | 0.5 | BrCc1ccccc1.C=CCC1(O)O[C@H](CO)[C@@H](O)[C@H](OC)[C@H]1O>CN(C)C=O>C=CCC1(O)O[C@H](COCc2ccccc2)[C@@H](OCc2ccccc2)[C@H](OC)[C@H]1OCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-df8ad700d0524d5dbe0290d4c136f968 | CCN(CC)CC.OC1OC[C@@H](O)[C@H](O)[C@H]1O>>C=CCC1(O)OC[C@@H](O)[C@H](O)[C@H]1O | OC1[C@H](O)[C@@H](O)[C@H](O)CO1.FC(S(=O)(=O)O)(F)F.C(C)N(CC)CC>>C(C=C)C1(O)[C@H](O)[C@@H](O)[C@H](O)CO1 | CCN([CH2:1]C)[CH2:3][CH3:2].[CH:4]1([OH:5])[O:6][CH2:7][C@@H:8]([OH:9])[C@H:10]([OH:11])[C@H:12]1[OH:13]>>[CH2:1]=[CH:2][CH2:3][C:4]1([OH:5])[O:6][CH2:7][C@@H:8]([OH:9])[C@H:10]([OH:11])[C@H:12]1[OH:13] | CCN(CC)CC.OC1OC[C@@H](O)[C@H](O)[C@H]1O | C=CCC1(O)OC[C@@H](O)[C@H](O)[C@H]1O | null | null | C(C=C)O | C-C Coupling | OtherReaction | 6411d57862789c812f7a1e2785e0e32bdd5bdb9657491692cae890b673e328d5 | da4b0d2a54a1e8bc31f063d4fb50b426f270269b4ed22f20855284531e33528e | C1CCOCC1 | C-C-N(-[CH2;D2;+0:1]-C)-[CH2;D2;+0:2]-[CH3;D1;+0:3].[C:4]-[C:5](-[O;D1;H1:6])-[CH;D3;+0:7](-[O;D1;H1:8])-[#8:9]-[C:10]>>[C:4]-[C:5](-[O;D1;H1:6])-[C;H0;D4;+0:7](-[O;D1;H1:8])(-[CH2;D2;+0:2]-[CH;D2;+0:3]=[CH2;D1;+0:1])-[#8:9]-[C:10] | null | [] | 0 | CELSIUS | 15 | MINUTE | Xylopyranose (15.0 g) was dissolved in allyl alcohol (150 mL) and trifluoromethane sulfonic acid (235 μL) was dropwise added 0° C. The reaction was stirred at 0° C. for 15 minutes and then heated at 80° C. for 4 hours. The reaction solution was then neutralized with triethylamine and evaporated to dryness. Chromatograp... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary alcohol.Tertiary amine | Ether.Tertiary alcohol.Allyl | C1CCOCC1 | C1CCOCC1 | C1CCOCC1 | Other | C(C=C)O | 0 | 0.25 | CCN(CC)CC.OC1OC[C@@H](O)[C@H](O)[C@H]1O>C(C=C)O>C=CCC1(O)OC[C@@H](O)[C@H](O)[C@H]1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-86fe5203ed9f4fbdb2fe14c9d318ed68 | OBr.OC1OC[C@@H](OCc2ccccc2)[C@H](OCc2ccccc2)[C@H]1OCc1ccccc1>>BrC1OC[C@@H](OCc2ccccc2)[C@H](OCc2ccccc2)[C@H]1OCc1ccccc1 | C(C1=CC=CC=C1)O[C@H]1C(O)OC[C@H]([C@@H]1OCC1=CC=CC=C1)OCC1=CC=CC=C1.CN(C)C=O.OBr>>C(C1=CC=CC=C1)O[C@H]1C(OC[C@H]([C@@H]1OCC1=CC=CC=C1)OCC1=CC=CC=C1)Br | O[Br:1].O[CH:2]1[O:3][CH2:4][C@@H:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[C@H:14]([O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[C@H:23]1[O:24][CH2:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1>>[Br:1][CH:2]1[O:3][CH2:4][C@@H:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[C@H:1... | OBr.OC1OC[C@@H](OCc2ccccc2)[C@H](OCc2ccccc2)[C@H]1OCc1ccccc1 | BrC1OC[C@@H](OCc2ccccc2)[C@H](OCc2ccccc2)[C@H]1OCc1ccccc1 | null | null | ClCCl | Functional Group Interconversion | OtherReaction | ca81d1ab25975c317067435fa62d56552402561ea09dc3fad1fcd10a49b516de | 4a24ab9366ad1597555eebbe459af51e23a50a6f7a19fd3b20b61e39b88af65c | c1ccc(CO[C@@H]2[C@@H](OCc3ccccc3)COC[C@H]2OCc2ccccc2)cc1 | O-[Br;H0;D1;+0:1].O-[CH;D3;+0:2](-[#8:3]-[C:4])-[C:5](-[#8:6])-[C:7]>>[#8:6]-[C:5](-[C:7])-[CH;D3;+0:2](-[Br;H0;D1;+0:1])-[#8:3]-[C:4] | null | [] | 0 | CELSIUS | 1 | HOUR | 2,3,4-tri-O-benzyl-xylopyranose was dissolved in dry dichloromethane (50 mL) and dry DMF (3.0 mL) was added. The reaction mixture was cooled at 0° C. and added dropwise oxayl bromide (1.4 mL). The reaction mixture was stirred for 1 hour at 0° to 5° C. and then diluted with dichloromethane (250 mL), washed with water (2... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary alcohol | Secondary halide | C1CCOCC1 | C1CCOCC1 | C1CCOCC1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | ClCCl | 0 | 1 | OBr.OC1OC[C@@H](OCc2ccccc2)[C@H](OCc2ccccc2)[C@H]1OCc1ccccc1>ClCCl>BrC1OC[C@@H](OCc2ccccc2)[C@H](OCc2ccccc2)[C@H]1OCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b359345567474302818835351c759593 | CO.O=C(O)Cc1ccccc1O>>COC(=O)Cc1ccccc1O | OC1=C(C=CC=C1)CC(=O)O.Cl.CO>>OC1=C(C=CC=C1)CC(=O)OC | [CH3:1][OH:2].O[C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[OH:12]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[OH:12] | CO.O=C(O)Cc1ccccc1O | COC(=O)Cc1ccccc1O | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[C;D1;H3:5]-[OH;D1;+0:6]>>[C;D1;H3:5]-[O;H0;D2;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4] | 92 | [{"value": 92.0, "product": "OC1=C(C=CC=C1)CC(=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 2-(Hydroxyphenyl)acetic acid (50 g) was added to a solution of hydrogen chloride in methanol [prepared from acetyl chloride (25 ml) and methanol (250 ml)]. The solution was stirred at room temperature for three hours and then allowed to stand overnight (fifteen hours). The resulting mixture was concentrated under reduc... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | null | null | 3 | CO.O=C(O)Cc1ccccc1O>>COC(=O)Cc1ccccc1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ff8ee1b2e9464ba793997011769a0de5 | BrCc1ccccc1.COC(=O)Cc1ccccc1O>>COC(=O)Cc1ccccc1OCc1ccccc1 | O.C([O-])([O-])=O.[K+].[K+].OC1=C(C=CC=C1)CC(=O)OC.C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)OC1=C(C=CC=C1)CC(=O)OC | Br[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[OH:12]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | BrCc1ccccc1.COC(=O)Cc1ccccc1O | COC(=O)Cc1ccccc1OCc1ccccc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | 83 | [{"value": 83.0, "product": "C(C1=CC=CC=C1)OC1=C(C=CC=C1)CC(=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Methyl (2-hydroxyphenyl)acetate (21.0 g) was dissolved in DMF (200 ml), and potassium carbonate (19.35 g) was added in one portion. Benzyl bromide (23.94 g) in DMF (50 ml) was added dropwise to this mixture, with stirring, at room temperature. After eighteen hours the mixture was poured into water (500 ml) and extracte... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | null | null | BrCc1ccccc1.COC(=O)Cc1ccccc1O>CN(C)C=O>COC(=O)Cc1ccccc1OCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-34185b3344f149daad0d7bc149c9dc48 | COC(=O)Cc1ccccc1OCc1ccccc1.COC=O>>COC(=O)C(=CO)c1ccccc1OCc1ccccc1 | O.C(C1=CC=CC=C1)OC1=C(C=CC=C1)CC(=O)OC.C(=O)OC.[H-].[Na+]>>C(C1=CC=CC=C1)OC1=C(C=CC=C1)C(C(=O)OC)=CO | [CH3:1][O:2][C:3](=[O:4])[CH2:5][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.CO[CH:6]=[O:7]>>[CH3:1][O:2][C:3](=[O:4])[C:5](=[CH:6][OH:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | COC(=O)Cc1ccccc1OCc1ccccc1.COC=O | COC(=O)C(=CO)c1ccccc1OCc1ccccc1 | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 96625d77e84283c0b3d12da7aa89224d3f1463a0c9daded8a4664af279e46c47 | 8580ed94a2dd8e44b9acc2872ac5603f42e85017f3ed552f3d73a2ad78c46917 | c1ccc(COc2ccccc2)cc1 | C-O-[CH;D2;+0:1]=[O;H0;D1;+0:2].[C;D1;H3:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[C;H0;D3;+0:7](=[CH;D2;+0:1]-[OH;D1;+0:2])-[c:8](:[c:9]):[c:10] | null | [] | 0 | CELSIUS | 2 | HOUR | A mixture of methyl 2-benzyloxyphenylacetate (26.99 g) and methyl formate (126.62 g) in dry DMF (300 ml) was added dropwise to a stirred suspension of sodium hydride (50% disp. in oil, 10.13 g) in DMF (300 ml) at 0° C. After stirring at 0° C. for two hours the mixture was poured into water (1000 ml) and washed with eth... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Ester.Enol | null | null | c1ccccc1.c1ccccc1 | HO- | CN(C)C=O | 0 | 2 | COC(=O)Cc1ccccc1OCc1ccccc1.COC=O>CN(C)C=O>COC(=O)C(=CO)c1ccccc1OCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b04a46ce4c88420bb722e57bd623063c | COC(=O)C(=CO)c1ccccc1OCc1ccccc1.COS(=O)(=O)OC.O.O=C([O-])[O-]>>CO/C=C(/C(=O)OC)c1ccccc1OCc1ccccc1.COC(=O)Cc1ccccc1OCc1ccccc1 | O.S(=O)(=O)(OC)OC.C(C1=CC=CC=C1)OC1=C(C=CC=C1)C(C(=O)OC)=CO.C([O-])([O-])=O.[K+].[K+]>>C(C1=CC=CC=C1)OC1=C(C=CC=C1)/C(/C(=O)OC)=C\OC.C(C1=CC=CC=C1)OC1=C(C=CC=C1)CC(=O)OC | [OH:2][CH:3]=[C:4]([C:5](=[O:6])[O:7][CH3:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.O=S(=O)(O[CH3:1])O[CH3:29].[OH2:34].[O-][C:25]([O-:24])=[O:26]>>[CH3:1][O:2]/[CH:3]=[C:4](/[C:5](=[O:6])[O:7][CH3:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[O:15][CH2:16][c:1... | COC(=O)C(=CO)c1ccccc1OCc1ccccc1.COS(=O)(=O)OC.O.O=C([O-])[O-] | CO/C=C(/C(=O)OC)c1ccccc1OCc1ccccc1.COC(=O)Cc1ccccc1OCc1ccccc1 | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | a58d1a35f0d0559f750e4ccf181d02e2200e90dc49e5336181bf59be37e44301 | dd4efefcda3ca4680010d4c32943365ea0e60014859128aab77d945ddc5cd5de | c1ccc(COc2ccccc2)cc1.c1ccc(COc2ccccc2)cc1 | O=S(=O)(-O-[CH3;D1;+0:1])-O-[CH3;D1;+0:2].[#8:3]-[C:4](=[O;D1;H0:5])-[C:6](-[c:7])=[C:8]-[OH;D1;+0:9].[O-;H0;D1:10]-[C;H0;D3;+0:11](-[O-])=[O;D1;H0:12].[OH2;D0;+0:13]>>[#8:3]-[C:4](=[O;D1;H0:5])/[C:6](-[c:7])=[C:8]/[O;H0;D2;+0:9]-[CH3;D1;+0:1].[C;D1;H3:14]-[O;H0;D2;+0:10]-[C;H0;D3;+0:11](=[O;D1;H0:12])-[C:15]-[c:16]1:[... | null | [] | null | null | null | null | The crude methyl 2-(2'-benzyloxyphenyl)-3-hydroxyacrylate was dissolved in dry DMF (100 ml) and potassium carbonate (29.0 g) was added in one portion. Dimethyl sulphate (16.00 g) in dry DMF (10 ml) was then added dropwise with stirring. After ninety minutes, water (300 ml) was added and the solution was extracted with ... | 10.6084/m9.figshare.5104873.v1 | null | Enol | Ester.Ether.Ether | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CN(C)C=O | null | null | COC(=O)C(=CO)c1ccccc1OCc1ccccc1.COS(=O)(=O)OC.O.O=C([O-])[O-]>CN(C)C=O>CO/C=C(/C(=O)OC)c1ccccc1OCc1ccccc1.COC(=O)Cc1ccccc1OCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-abcb076a0ce4404db4518ad1d1b0ccf4 | CCCCC#CCCO>>C#CCCCCCCO | NCCCN.C(CC#CCCCC)O>>C(CCCCCC#C)O | [C:1]([CH2:2][CH2:3][CH2:4][CH3:5])#[C:6][CH2:7][CH2:8][OH:9]>>[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9] | CCCCC#CCCO | C#CCCCCCCO | null | null | CCCCCC | Functional Group Interconversion | OtherReaction | 717941f395a910361dbd079f0406c8739db3d600df9659ab84f995c3dd1e77a5 | f5163dfbf670ee9f38d1be788eef0e0a983df5868f48fe01d48741d6a3f98157 | null | [C:1]-[C:2]-[C;H0;D2;+0:3]#[C;H0;D2;+0:4]-[CH2;D2;+0:5]-[C:6]-[C:7]-[CH3;D1;+0:8]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:8]-[C:7]-[C:6]-[C;H0;D2;+0:5]#[CH;D1;+0:4] | null | [] | null | null | null | null | 35% KH in mineral oil (27 g, 240 mmol) under an argon atmosphere was washed with hexane and treated dropwise with 1,3-diaminopropane. The mixture was stirred at room temperature until it became homogeneous. The flask was cooled to 0∞C. and 3-octyn-1-ol (10 g, 79 mmol, Lancaster Synthesis) was slowly added. The reaction... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | Alkyne | null | null | null | null | CCCCCC | null | null | CCCCC#CCCO>CCCCCC>C#CCCCCCCO |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-012466477a7d413f8af56362a0621f75 | CCCCC#CCCO>>C#CCCCCCCO | C(CC#CCCCC)O.[H-].[K+].NCCCN>>C(CCCCCC#C)O | [CH3:1][CH2:2][CH2:3][CH2:4][C:5]#[C:6][CH2:7][CH2:8][OH:9]>>[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9] | CCCCC#CCCO | C#CCCCCCCO | null | null | CCCCCC | Miscellaneous | OtherReaction | 1dc82b94ad0bb9c37129929afef1fa70f760dcdf2017a728c72d09b3d0dbf429 | 7b33466a2cc81bfe95f125510ec1a59cf92dd3caaf14f1a960631fc63bb0a68b | null | [C:1]-[C:2]-[C;H0;D2;+0:3]#[C;H0;D2;+0:4]-[C:5]-[C:6]-[CH2;D2;+0:7]-[CH3;D1;+0:8]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[C:5]-[C:6]-[C;H0;D2;+0:7]#[CH;D1;+0:8] | null | [] | null | null | null | null | Potassium hydride, (35%) in mineral oil (27 g, 240 mmol) under an argon atmosphere was washed with hexane and treated dropwise with 1,3-diaminopropane. The mixture was stirred at room temperature until it became homogeneous. The flask was cooled to 0° C. and 3-octyn-1-ol (10 g, 79 mmol, Lancaster Synthesis) was slowly ... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | Alkyne | null | null | null | null | CCCCCC | null | null | CCCCC#CCCO>CCCCCC>C#CCCCCCCO |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e5a9b22eb8bd40e6869c9b589c0e99c1 | COc1ccc(CCCCCCCCO)cc1.II>>COc1ccc(CCCCCCCCI)cc1 | N1C=NC=C1.COC1=CC=C(C=C1)CCCCCCCCO.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N1C=NC=C1.II>>ICCCCCCCCC1=CC=C(C=C1)OC | O[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:17][cH:16]1.I[I:15]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][I:15])[cH:16][cH:17]1 | COc1ccc(CCCCCCCCO)cc1.II | COc1ccc(CCCCCCCCI)cc1 | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccccc1 | I-[I;H0;D1;+0:1].O-[CH2;D2;+0:2]-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:2]-[I;H0;D1;+0:1] | null | [] | 65 | CELSIUS | null | null | To a stirred solution of 8-(4-methoxyphenyl)octan-1-ol (12.3 g, 52 mmol) in dry toluene (200 mL) under an argon atmosphere was added triphenylphosphine (17.8 g, 67.6 mmol) and imidazole (10.6 g, 156 mmol). After the imidazole had dissolved, I2 (17.1 g, 67.6 mmol) was added. The reaction was then heated at 65° C. for 30... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccccc1 | HI | C1(=CC=CC=C1)C | 65 | null | COc1ccc(CCCCCCCCO)cc1.II>C1(=CC=CC=C1)C>COc1ccc(CCCCCCCCI)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-bb0e1e7df8314c9ba14cdb118f699551 | CCCCCCCCCCCCOc1ccc(C)nc1/C=C/CC(=O)O.O=C(OO)c1cccc(Cl)c1>>CCCCCCCCCCCCOc1ccc(C)[n+]([O-])c1/C=C/CC(=O)O | C(=O)(O)C/C=C/C1=NC(=CC=C1OCCCCCCCCCCCC)C.ClC=1C=C(C(=O)OO)C=CC1.C(=O)(O)[O-].[Na+]>>C(=O)(O)C/C=C/C1=[N+](C(=CC=C1OCCCCCCCCCCCC)C)[O-] | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][c:14]1[cH:15][cH:16][c:17]([CH3:18])[n:19][c:21]1/[CH:22]=[CH:23]/[CH2:24][C:25](=[O:26])[OH:27].O=C(O[OH:20])c1cccc(Cl)c1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][c:14]1[c... | CCCCCCCCCCCCOc1ccc(C)nc1/C=C/CC(=O)O.O=C(OO)c1cccc(Cl)c1 | CCCCCCCCCCCCOc1ccc(C)[n+]([O-])c1/C=C/CC(=O)O | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 5b2b5a1eb88c9671c4a604b6f76054cc01cd86a1985fc147f7e56f19c4844d35 | 98b338a9d01476c0929fd5672e7509121bfe69600fd72e4d1cc6f1782e2d05d9 | c1cc[nH+]cc1 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[C;D1;H3:2]-[c:3](:[c:4]):[n;H0;D2;+0:5]:[c:6](/[C:7]=[C:8]/[C:9]-[C:10](=[O;D1;H0:11])-[O;D1;H1:12]):[c:13]>>[C;D1;H3:2]-[c:3](:[c:4]):[n+;H0;D3:5](-[O-;H0;D1:1]):[c:6](/[C:7]=[C:8]/[C:9]-[C:10](=[O;D1;H0:11])-[O;D1;H1:12]):[c:13] | null | [] | null | null | 30 | MINUTE | 2-(E-2-Carboxymethylethenyl)-3-dodecyloxy-6-methylpyridine (2.15 g, 5.95 mmol) was dissolved in dry CH2Cl2 (20 mL) and cooled to 0∞C.; 85% m-chloroperoxybenzoic acid (1.45 g, 7.14 mmol) was added and the reaction was stirred at 0∞C. for 30 minutes and at room temperature for 16 hours. The reaction solution was poured i... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide | null | c1ccncc1.c1ccccc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | HCl | C(Cl)Cl | null | 0.5 | CCCCCCCCCCCCOc1ccc(C)nc1/C=C/CC(=O)O.O=C(OO)c1cccc(Cl)c1>C(Cl)Cl>CCCCCCCCCCCCOc1ccc(C)[n+]([O-])c1/C=C/CC(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-56b9447d44f64098b2f16a6ad9eaa5d8 | CCCCCCCCCCCCOc1ccc(CO)nc1/C=C/CC(=O)O.O=S(Cl)Cl>>CCCCCCCCCCCCOc1ccc(CCl)nc1/C=C/CC(=O)O.Cl | C(=O)(O)C/C=C/C1=NC(=CC=C1OCCCCCCCCCCCC)CO.S(=O)(Cl)Cl>>Cl.C(=O)(O)C/C=C/C1=NC(=CC=C1OCCCCCCCCCCCC)CCl | O[CH2:18][c:17]1[cH:16][cH:15][c:14]([O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:21](/[CH:22]=[CH:23]/[CH2:24][C:25](=[O:26])[OH:27])[n:20]1.O=S([Cl:19])[Cl:28]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][c:14]1[cH:1... | CCCCCCCCCCCCOc1ccc(CO)nc1/C=C/CC(=O)O.O=S(Cl)Cl | CCCCCCCCCCCCOc1ccc(CCl)nc1/C=C/CC(=O)O.Cl | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | Alcohol to chloride_SOCl2 | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccncc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5]/[C:6]=[C:7].O=S(-[Cl;H0;D1;+0:8])-[Cl;H0;D1;+0:9]>>[C:7]=[C:6]/[c:5]:[#7;a:4]:[c:2](-[CH2;D2;+0:1]-[Cl;H0;D1;+0:8]):[c:3].[ClH;D0;+0:9] | null | [] | null | null | 1 | HOUR | 2-(E-2-Carboxymethylethenyl)-3-dodecyloxy-6-(hydroxymethyl)pyridine (250 mg, 0.662 mmol) was dissolved in dry toluene (10 mL) under an argon atmosphere and cooled to 0∞C. Thionyl chloride (0.50 mL, 6.85 mmol) was slowly added and the solution was stirred at 0∞C. for 30 minutes followed by 1 h at room temperature. The s... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccncc1 | Other | C1(=CC=CC=C1)C | null | 1 | CCCCCCCCCCCCOc1ccc(CO)nc1/C=C/CC(=O)O.O=S(Cl)Cl>C1(=CC=CC=C1)C>CCCCCCCCCCCCOc1ccc(CCl)nc1/C=C/CC(=O)O.Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6d5c70c0bd0043a78a39a3c35601adba | CCCCC#CCCO>>C#CCCCCCCO | NCCCN.C(CC#CCCCC)O>>C(CCCCCC#C)O | [C:1]([CH2:2][CH2:3][CH2:4][CH3:5])#[C:6][CH2:7][CH2:8][OH:9]>>[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9] | CCCCC#CCCO | C#CCCCCCCO | null | null | CCCCCC | Functional Group Interconversion | OtherReaction | 717941f395a910361dbd079f0406c8739db3d600df9659ab84f995c3dd1e77a5 | f5163dfbf670ee9f38d1be788eef0e0a983df5868f48fe01d48741d6a3f98157 | null | [C:1]-[C:2]-[C;H0;D2;+0:3]#[C;H0;D2;+0:4]-[CH2;D2;+0:5]-[C:6]-[C:7]-[CH3;D1;+0:8]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:8]-[C:7]-[C:6]-[C;H0;D2;+0:5]#[CH;D1;+0:4] | null | [] | null | null | null | null | 35% KH in mineral oil (27 g, 240 mmol) under an argon atmosphere was washed with hexane and treated dropwise with 1,3-diaminopropane. The mixture was stirred at room temperature until it became homogeneous. The flask was cooled to 0° C. and 3-octyn-1-ol (10 g, 79 mmol, Lancaster Synthesis) was slowly added. The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | Alkyne | null | null | null | null | CCCCCC | null | null | CCCCC#CCCO>CCCCCC>C#CCCCCCCO |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5247f69c87d84750ba3f98831c15b7fa | COc1ccc(CCCCCCCCOc2ccc(C)nc2/C=C/CC(=O)O)cc1.O=C(OO)c1cccc(Cl)c1>>COc1ccc(CCCCCCCCOc2ccc(C)[n+]([O-])c2/C=C/CC(=O)O)cc1 | C(=O)(O)C/C=C/C1=NC(=CC=C1OCCCCCCCCC1=CC=C(C=C1)OC)C.C1=CC(=CC(=C1)Cl)C(=O)OO>>C(=O)(O)C/C=C/C1=[N+](C(=CC=C1OCCCCCCCCC1=CC=C(C=C1)OC)C)[O-] | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][c:16]2[cH:17][cH:18][c:19]([CH3:20])[n:21][c:23]2/[CH:24]=[CH:25]/[CH2:26][C:27](=[O:28])[OH:29])[cH:30][cH:31]1.O=C(O[OH:22])c1cccc(Cl)c1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH... | COc1ccc(CCCCCCCCOc2ccc(C)nc2/C=C/CC(=O)O)cc1.O=C(OO)c1cccc(Cl)c1 | COc1ccc(CCCCCCCCOc2ccc(C)[n+]([O-])c2/C=C/CC(=O)O)cc1 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 5b2b5a1eb88c9671c4a604b6f76054cc01cd86a1985fc147f7e56f19c4844d35 | 98b338a9d01476c0929fd5672e7509121bfe69600fd72e4d1cc6f1782e2d05d9 | c1ccc(CCCCCCCCOc2ccc[nH+]c2)cc1 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[C;D1;H3:2]-[c:3](:[c:4]):[n;H0;D2;+0:5]:[c:6](/[C:7]=[C:8]/[C:9]-[C:10](=[O;D1;H0:11])-[O;D1;H1:12]):[c:13]>>[C;D1;H3:2]-[c:3](:[c:4]):[n+;H0;D3:5](-[O-;H0;D1:1]):[c:6](/[C:7]=[C:8]/[C:9]-[C:10](=[O;D1;H0:11])-[O;D1;H1:12]):[c:13] | null | [] | 0 | CELSIUS | 15 | HOUR | 2-(E-2-Carboxymethylethenyl)-3-[8-(4-methoxyphenyl)octyloxy]-6-methylpyridine (17.1 g, 41.5 mmol) was dissolved in dry CH2Cl2 (105 mL) and cooled to 0° C.; 50% mCPBA (15.8 g, 45.8 mmol) was added in three portions over 10 minutes. The cooling bath was removed and the reaction was stirred for 15 hours at room temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide | null | c1ccncc1.c1ccccc1 | C1=CC=[NH+]C=C1 | c1ccccc1.C1=CC=[NH+]C=C1 | HCl | C(Cl)Cl | 0 | 15 | COc1ccc(CCCCCCCCOc2ccc(C)nc2/C=C/CC(=O)O)cc1.O=C(OO)c1cccc(Cl)c1>C(Cl)Cl>COc1ccc(CCCCCCCCOc2ccc(C)[n+]([O-])c2/C=C/CC(=O)O)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-88aa2d2c0607465cb96b3991fe722e52 | COc1ccc(CCCCCCCCOc2ccc(C)nc2/C=C/CC(=O)O)cc1.O=C(OO)c1cccc(Cl)c1>>COc1ccc(CCCCCCCCOc2ccc(C)[n+]([O-])c2/C=C/CC(=O)O)cc1 | C(=O)(O)C/C=C/C1=NC(=CC=C1OCCCCCCCCC1=CC=C(C=C1)OC)C.ClC1=CC(=CC=C1)C(=O)OO>>C(=O)(O)C/C=C/C1=[N+](C(=CC=C1OCCCCCCCCC1=CC=C(C=C1)OC)C)[O-] | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][c:16]2[cH:17][cH:18][c:19]([CH3:20])[n:21][c:23]2/[CH:24]=[CH:25]/[CH2:26][C:27](=[O:28])[OH:29])[cH:30][cH:31]1.O=C(O[OH:22])c1cccc(Cl)c1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH... | COc1ccc(CCCCCCCCOc2ccc(C)nc2/C=C/CC(=O)O)cc1.O=C(OO)c1cccc(Cl)c1 | COc1ccc(CCCCCCCCOc2ccc(C)[n+]([O-])c2/C=C/CC(=O)O)cc1 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 5b2b5a1eb88c9671c4a604b6f76054cc01cd86a1985fc147f7e56f19c4844d35 | 98b338a9d01476c0929fd5672e7509121bfe69600fd72e4d1cc6f1782e2d05d9 | c1ccc(CCCCCCCCOc2ccc[nH+]c2)cc1 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[C;D1;H3:2]-[c:3](:[c:4]):[n;H0;D2;+0:5]:[c:6](/[C:7]=[C:8]/[C:9]-[C:10](=[O;D1;H0:11])-[O;D1;H1:12]):[c:13]>>[C;D1;H3:2]-[c:3](:[c:4]):[n+;H0;D3:5](-[O-;H0;D1:1]):[c:6](/[C:7]=[C:8]/[C:9]-[C:10](=[O;D1;H0:11])-[O;D1;H1:12]):[c:13] | null | [] | 0 | CELSIUS | 15 | HOUR | 2-(E-2-Carboxymethyl-ethenyl)-3-[8-(4-methoxyphenyl)octyloxy]-6-methylpyridine (17.1 g, 41.5 mmol) was dissolved in dry CH2Cl2 (105 mL) and cooled to 0° C.; 50% m-chlorperbenzoic acid (15.8 g, 45.8 mmol) was added in three portions over 10 minutes. The cooling bath was removed and the reaction was stirred for 15 hours ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide | null | c1ccncc1.c1ccccc1 | C1=CC=[NH+]C=C1 | c1ccccc1.C1=CC=[NH+]C=C1 | HCl | C(Cl)Cl | 0 | 15 | COc1ccc(CCCCCCCCOc2ccc(C)nc2/C=C/CC(=O)O)cc1.O=C(OO)c1cccc(Cl)c1>C(Cl)Cl>COc1ccc(CCCCCCCCOc2ccc(C)[n+]([O-])c2/C=C/CC(=O)O)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-32928277e9554e8f846f58e8123833be | COC(=O)c1cccc(CBr)c1.NC(N)=S>>COC(=O)c1cccc(CS)c1 | BrCC=1C=C(C(=O)OC)C=CC1.NC(=S)N>>SCC=1C=C(C(=O)OC)C=CC1 | Br[CH2:10][c:9]1[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:12]1.NC(N)=[S:11]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([CH2:10][SH:11])[cH:12]1 | COC(=O)c1cccc(CBr)c1.NC(N)=S | COC(=O)c1cccc(CS)c1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 874b82c2d4f05e98f462796ed8d7ef1e13fce4a8a588b04aa02ed1f40755b5a0 | c5ac5fd8ad86e4dc1842d4270aab48696f24c3999504096b608528878069554b | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].N-C(-N)=[S;H0;D1;+0:5]>>[SH;D1;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 2 | DAY | To a solution of methyl 3-bromomethylbenzoate (6.9 g, 30 mmol; Lancaster) in dry acetone (10 mL) was added via dropwise addition a solution of thiourea (2.28 g, 30 mmol) in dry acetone (40 mL) at room temperature. After 15 minutes the precipitated thiouronium salt was collected by filtration; the solids were washed wit... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiourea | Aliphatic thiol | null | null | c1ccccc1 | HBr | CC(=O)C | null | 48 | COC(=O)c1cccc(CBr)c1.NC(N)=S>CC(=O)C>COC(=O)c1cccc(CS)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-378418b0f968496da9d02d2ceabcfed2 | BrC1CCCC1.COc1ccc(C=O)cc1O>>COc1ccc(C=O)cc1OC1CCCC1 | C([O-])([O-])=O.[Cs+].[Cs+].OC=1C=C(C=O)C=CC1OC.C1(CCCC1)Br.C1(CCCC1)Br.C([O-])([O-])=O.[Cs+].[Cs+]>>C1(CCCC1)OC=1C=C(C=O)C=CC1OC | Br[CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[cH:9][c:10]1[OH:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[cH:9][c:10]1[O:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1 | BrC1CCCC1.COc1ccc(C=O)cc1O | COc1ccc(C=O)cc1OC1CCCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | b21417a59456fdb6c9e74dab1ba6f82edc34a079e35c8c3647ac7fef47b6d270 | cf768afb66ed5041aefdce1fa6d1e40995a1ab7c4b4a4ca47544fe49ee1e629f | c1ccc(OC2CCCC2)cc1 | Br-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1.[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[O;H0;D2;+0:6]-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1):[c:9] | 89.4 | [{"value": 89.4, "product": "C1(CCCC1)OC=1C=C(C=O)C=CC1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Caesium carbonate (214 g, 0.66 mol) was added to a mixture of 3-hydroxy-4-methoxybenzaldehyde (100 g, 0.66 mol) and cyclopentyl bromide (98 g, 0.66 mol) in anhydrous DMF (50 ml). The reaction mixture was stirred at RT for 16 h then treated with a further portion of cyclopentyl bromide (98 g, 0.66 mol) and caesium carbo... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic alcohol | Ether | C1CCCC1 | C1CCCC1 | c1ccccc1.C1CCCC1 | HBr | CN(C)C=O | null | 16 | BrC1CCCC1.COc1ccc(C=O)cc1O>CN(C)C=O>COc1ccc(C=O)cc1OC1CCCC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-89cc579f3b55493b927b4858bac1ec2f | BrOC1CCCC1.COc1ccc(CO)cc1O>>COc1ccc(CO)cc1OC1CCCC1 | C([O-])([O-])=O.[Cs+].[Cs+].OC=1C=C(CO)C=CC1OC.[I-].[Na+].C1(CCCC1)OBr>>C1(CCCC1)OC=1C=C(CO)C=CC1OC | BrO[CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[cH:9][c:10]1[OH:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[cH:9][c:10]1[O:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1 | BrOC1CCCC1.COc1ccc(CO)cc1O | COc1ccc(CO)cc1OC1CCCC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1b0b141bf6b317fb3f4853d99c0e21f208620be70a498da9a42860eb95c70530 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | c1ccc(OC2CCCC2)cc1 | Br-O-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1.[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[O;H0;D2;+0:6]-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1):[c:9] | 35.8 | [{"value": 35.8, "product": "C1(CCCC1)OC=1C=C(CO)C=CC1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | From 3-hydroxy-4-methoxybenzyl alcohol (50 g, 0.324 mol), cyclopentyloxybromide (70 ml, 0.648 mol), caesium carbonate (72.83 g, 0.222 mol) and sodium iodide (5.63 g, 0.037 mol). Chromatography (SiO2 ; EtOAc-C6H14. 1:3) to yield the title compound (25.782 g). (Found C, 69.92; H, 8.18. C13H18O3 requires C, 70.25; H, 8.16... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | C1CCCC1 | C1CCCC1 | c1ccccc1.C1CCCC1 | HBr | null | null | null | BrOC1CCCC1.COc1ccc(CO)cc1O>>COc1ccc(CO)cc1OC1CCCC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0c5e70e577c94e38b27d7cec9a37378c | CI.Clc1cncc(Cl)c1>>Cc1c(Cl)cncc1Cl | ClC=1C=NC=C(C1)Cl.[Li+].CC(C)[N-]C(C)C.C(O)([O-])=O.[Na+].IC>>ClC=1C=NC=C(C1C)Cl | I[CH3:1].[cH:2]1[c:3]([Cl:4])[cH:5][n:6][cH:7][c:8]1[Cl:9]>>[CH3:1][c:2]1[c:3]([Cl:4])[cH:5][n:6][cH:7][c:8]1[Cl:9] | CI.Clc1cncc(Cl)c1 | Cc1c(Cl)cncc1Cl | null | null | ClCCl.C1CCOC1 | C-C Coupling | Methylation with MeI_aryl | d4dc1d398fcb789be26f861c3ffb23cfce3504c400401ddf0ee0bd40e14a762b | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | c1ccncc1 | I-[CH3;D1;+0:1].[Cl;D1;H0:2]-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[c:7](-[Cl;D1;H0:8]):[cH;D2;+0:9]:1>>[CH3;D1;+0:1]-[c;H0;D3;+0:9]1:[c:3](-[Cl;D1;H0:2]):[c:4]:[#7;a:5]:[c:6]:[c:7]:1-[Cl;D1;H0:8] | 53 | [{"value": 53.0, "product": "ClC=1C=NC=C(C1C)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | 3,5-Dichloropyridine (2.04 g, 13.5 mmol) in THF (5 ml) was added dropwise to a solution of LDA [prepared from diisopropylamine (1.9 ml, 13.5 mmol) and n-butyllithium (1.6M, 8.4 ml, 13.5 mmol)] in THF (25 ml) at -70° C. After stirring at this temperature for 5 min, iodomethane (0.85 ml, 13.5 mmol) was added and the reac... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccncc1 | c1ccncc1 | c1ccncc1 | HI | ClCCl.C1CCOC1 | null | 0.083333 | CI.Clc1cncc(Cl)c1>ClCCl.C1CCOC1>Cc1c(Cl)cncc1Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4c51ec94fbde4e1a8f48e64a30ce3af0 | CCCCCC.CCOC(C)=O.CCOC(C)=O.CO.Cc1ccncc1.[Li][CH2]CCC>>COc1ccc(C(O)Cc2ccncc2)cc1OC1CCCC1 | CCOC(=O)C.CCCCCC.CCOC(=O)C.CO.CC1=CC=NC=C1.C(CCC)[Li]>>C1(CCCC1)OC=1C=C(C=CC1OC)C(CC1=CC=NC=C1)O | CCC[CH2:5]C[CH3:20].CC(=O)O[CH2:16][CH3:17].[CH2:3]([CH3:4])[O:18][C:7]([CH3:6])=[O:8].[CH3:1][OH:2].[CH3:9][c:10]1[cH:11][cH:12][n:13][cH:14][cH:15]1.[Li][CH2:21][CH2:22][CH2:23][CH3:19]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([OH:8])[CH2:9][c:10]2[cH:11][cH:12][n:13][cH:14][cH:15]2)[cH:16][c:17]1[O:18][CH:19]1[CH... | CCCCCC.CCOC(C)=O.CCOC(C)=O.CO.Cc1ccncc1.[Li][CH2]CCC | COc1ccc(C(O)Cc2ccncc2)cc1OC1CCCC1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 4d5b9d11b173cddc7c9965df48907cd64074ac172a04e8355236d47d1d33a538 | eaed0ec2e18ddd7689918b523da6af01c4c12f36db516a28cad5374c79aa54fd | c1cc(CCc2ccncc2)cc(OC2CCCC2)c1 | C-C(=O)-O-[CH2;D2;+0:1]-[CH3;D1;+0:2].C-C-C-[CH2;D2;+0:3]-C-[CH3;D1;+0:4].[C;D1;H3:5]-[OH;D1;+0:6].[CH3;D1;+0:7]-[CH2;D2;+0:8]-[O;H0;D2;+0:9]-[C;H0;D3;+0:10](-[CH3;D1;+0:11])=[O;H0;D1;+0:12].[CH3;D1;+0:13]-[C:14]-[C:15]-[CH2;D2;+0:16]-[Li].[CH3;D1;+0:17]-[c:18]1:[c:19]:[c:20]:[#7;a:21]:[c:22]:[c:23]:1>>[C;D1;H3:5]-[O;H... | null | [] | null | null | null | null | From 4-methylpyridine (3.00 g, 32.1 mmol); n-butyllithium (32.1 mmol), and Intermediate 1 (6.82 g, 31.0 mmol). The crude product was subject to chromatography [SiO2 ; EtOAc-hexane, 3:2 (500 ml) to 4:1 (1000 ml) then EtOAc-methanol 9:1 (1500 ml)] to afford the title compound. (9.68 g) as fine white needles m.p. 97°-101°... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Methanol.Alkyl lithium | Ether.Ether.Secondary alcohol | null | c1ccccc1.C1CCCC1 | c1ccccc1.c1ccncc1.C1CCCC1 | HO-.Li | null | null | null | CCCCCC.CCOC(C)=O.CCOC(C)=O.CO.Cc1ccncc1.[Li][CH2]CCC>>COc1ccc(C(O)Cc2ccncc2)cc1OC1CCCC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-46541465def6464b8e0702bdac2c409a | COc1ccc(-c2ccccc2[P+](C)(c2ccccc2)c2ccccc2)cc1OC1CCCC1.O=Cc1ccncc1>>COc1ccc(/C=C\c2ccncc2)cc1OC1CCCC1 | [O-]CC.[Na+].N1=CC=C(C=C1)C=O.[Cl-].C1(CCCC1)OC=1C=C(C=CC1OC)C1=C(C=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C>>C1(CCCC1)OC=1C=C(C=CC1OC)\C=C/C1=CC=NC=C1 | C[P+](c1ccccc1)(c1ccccc1)c1cccc[c:7]1-[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:16]([O:17][CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22]2)[cH:15]1.O=[CH:8][c:9]1[cH:10][cH:11][n:12][cH:13][cH:14]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](/[CH:7]=[CH:8]\[c:9]2[cH:10][cH:11][n:12][cH:13][cH:14]2)[cH:15][c:16]1[O:17][CH:18]1[CH2:19][... | COc1ccc(-c2ccccc2[P+](C)(c2ccccc2)c2ccccc2)cc1OC1CCCC1.O=Cc1ccncc1 | COc1ccc(/C=C\c2ccncc2)cc1OC1CCCC1 | null | null | C(C)O | C-C Coupling | OtherReaction | cb5f277ac55a0e763ef643becc05f1522019cc4161daceb249ed2d634b78153b | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | C(=C\c1cccc(OC2CCCC2)c1)\c1ccncc1 | C-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].O=[CH;D2;+0:7]-[c:8]1:[c:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1>>[c:4]:[c:3]:[c;H0;D3;+0:2](/[CH;D2;+0:1]=[CH;D2;+0:7]\[c:8]1:[c:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1):[c:5]:[c:6] | 11.9 | [{"value": 11.9, "product": "C1(CCCC1)OC=1C=C(C=CC1OC)\\C=C/C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of sodium ethoxide [prepared from sodium (0.10 g, 4.50 mmol)] in ethanol (50 ml) was added over 5 min to a stirred mixture of 4-pyridine carboxaldehyde (0.44 g, 4.10 mmol) and (3-cyclopentyloxy-4-methoxyphenyl)-methyltriphenylphosphonium chloride (2.00 g, 4.08 g) in ethanol (30 ml). After 2 h, the reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1.c1ccncc1.C1CCCC1 | HO- | C(C)O | null | 2 | COc1ccc(-c2ccccc2[P+](C)(c2ccccc2)c2ccccc2)cc1OC1CCCC1.O=Cc1ccncc1>C(C)O>COc1ccc(/C=C\c2ccncc2)cc1OC1CCCC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-95ef5c03630f4827baa473fbaab9413f | C=CC#N.CCOC(=O)CN>>CCOC(=O)CNCCC#N | Cl.C(C)OC(CN)=O.[OH-].[K+].C(C=C)#N>>C(C)OC(CNCCC#N)=O | [CH2:8]=[CH:9][C:10]#[N:11].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][NH2:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][NH:7][CH2:8][CH2:9][C:10]#[N:11] | C=CC#N.CCOC(=O)CN | CCOC(=O)CNCCC#N | null | null | O | Heteroatom Alkylation and Arylation | aza-Michael addition primary | b45dd075b7e75caee6dc0a68cb402266c75e0848f7502f06a5dbd8a34863aae2 | 2e45960e6468a140db4162555f247a2535630c23e1aa16e082b84ce22691ebbf | null | [CH2;D1;+0:1]=[CH;D2;+0:2]-[C:3]#[N;D1;H0:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]-[NH2;D1;+0:10]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]-[NH;D2;+0:10]-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[C:3]#[N;D1;H0:4] | 48 | [{"value": 48.0, "product": "C(C)OC(CNCCC#N)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 139.6g (1 mole) of glycine ethyl ester hydrochloride was dissolved in 80 ml of distilled water and to this solution was added 230 ml of an aqueous solution of 67.3 g (1.2 mole eq.) of potassium hydroxide. Then, 106.2 g (2 mole eq.) of acrylonitrile was added to the reaction solution while heating and stirring at 50° to... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Vinyl | Secondary amine | null | null | null | null | O | null | null | C=CC#N.CCOC(=O)CN>O>CCOC(=O)CNCCC#N |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9e63e16f353541c69b169a8401ad9d31 | CC(C)(C)ON=C1CNCC1CN.O=C(O)c1cn(C2CC2)c2c(F)c(F)c(F)cc2c1=O>>CC(C)(C)ON=C1CN(c2c(F)cc3c(=O)c(C(=O)O)cn(C4CC4)c3c2F)CC1CN | C1(CC1)N1C=C(C(C2=CC(=C(C(=C12)F)F)F)=O)C(=O)O.Cl.Cl.NCC1CNCC1=NOC(C)(C)C>>NCC1CN(CC1=NOC(C)(C)C)C1=C(C=C2C(C(=CN(C2=C1F)C1CC1)C(=O)O)=O)F | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][N:6]=[C:7]1[CH2:8][NH:9][CH2:29][CH:30]1[CH2:31][NH2:32].F[c:10]1[c:11]([F:12])[cH:13][c:14]2[c:15](=[O:16])[c:17]([C:18](=[O:19])[OH:20])[cH:21][n:22]([CH:23]3[CH2:24][CH2:25]3)[c:26]2[c:27]1[F:28]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][N:6]=[C:7]1[CH2:8][N:9]([c:10]2[c:11]([F:12])[cH... | CC(C)(C)ON=C1CNCC1CN.O=C(O)c1cn(C2CC2)c2c(F)c(F)c(F)cc2c1=O | CC(C)(C)ON=C1CN(c2c(F)cc3c(=O)c(C(=O)O)cn(C4CC4)c3c2F)CC1CN | null | null | null | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 89f800d0b5c6eace023ec0f16ed65844f5dd409e156b3b4845e1db5de9a38872 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | N=C1CCN(c2ccc3c(=O)ccn(C4CC4)c3c2)C1 | F-[c;H0;D3;+0:1]1:[c:2](-[F;D1;H0:3]):[c:4]:[c:5]:[c:6](:[#7;a:7](-[C:8]):[c:9]):[c:10]:1-[F;D1;H0:11].[#7:12]=[C:13]1-[C:14]-[C:15]-[NH;D2;+0:16]-[C:17]-1>>[#7:12]=[C:13]1-[C:14]-[C:15]-[N;H0;D3;+0:16](-[c;H0;D3;+0:1]2:[c:2](-[F;D1;H0:3]):[c:4]:[c:5]:[c:6](:[#7;a:7](-[C:8]):[c:9]):[c:10]:2-[F;D1;H0:11])-[C:17]-1 | 67.3 | [{"value": 67.0, "product": "NCC1CN(CC1=NOC(C)(C)C)C1=C(C=C2C(C(=CN(C2=C1F)C1CC1)C(=O)O)=O)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.3, "product": "NCC1CN(CC1=NOC(C)(C)C)C1=C(C=C2C(C(=CN(C2=C1F)C1CC1)C(=O)O)=O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 141 mg (0.5 mmole) of 1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid and 143 mg (0.55 mmole) of 3-aminomethyl-4-t-butyloxyiminopyrrolidine dihydrochloride were refluxed for 2.5 hours under heating according to the same manner as Example 89 and cooled down to room temperature. Then, the resul... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccc2ncccc2c1 | C1CC[NH]C1.c1ccc2ncccc2c1 | C1CC[NH]C1.c1ccc2ncccc2c1.C1CC1 | HF | null | null | null | CC(C)(C)ON=C1CNCC1CN.O=C(O)c1cn(C2CC2)c2c(F)c(F)c(F)cc2c1=O>>CC(C)(C)ON=C1CN(c2c(F)cc3c(=O)c(C(=O)O)cn(C4CC4)c3c2F)CC1CN |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1eee3fd255824bfab45a5acac194afe1 | CC(C)(C)ON=C1CNCC1CN.O=C(O)c1cn(-c2ccc(F)cc2F)c2nc(F)c(F)cc2c1=O>>CC(C)(C)ON=C1CN(c2nc3c(cc2F)c(=O)c(C(=O)O)cn3-c2ccc(F)cc2F)CC1CN | FC=1C=C2C(C(=CN(C2=NC1F)C1=C(C=C(C=C1)F)F)C(=O)O)=O.Cl.Cl.NCC1CNCC1=NOC(C)(C)C.N12CCCCCC2=NCCC1>>NCC1CN(CC1=NOC(C)(C)C)C1=C(C=C2C(C(=CN(C2=N1)C1=C(C=C(C=C1)F)F)C(=O)O)=O)F | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][N:6]=[C:7]1[CH2:8][NH:9][CH2:33][CH:34]1[CH2:35][NH2:36].F[c:10]1[n:11][c:12]2[c:13]([cH:14][c:15]1[F:16])[c:17](=[O:18])[c:19]([C:20](=[O:21])[OH:22])[cH:23][n:24]2-[c:25]1[cH:26][cH:27][c:28]([F:29])[cH:30][c:31]1[F:32]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][N:6]=[C:7]1[CH2:8][N:9]([... | CC(C)(C)ON=C1CNCC1CN.O=C(O)c1cn(-c2ccc(F)cc2F)c2nc(F)c(F)cc2c1=O | CC(C)(C)ON=C1CN(c2nc3c(cc2F)c(=O)c(C(=O)O)cn3-c2ccc(F)cc2F)CC1CN | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 8e57f376730c9014acd2fa503b42327b9db31ded66ca38cadcf6d11720f7e268 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | N=C1CCN(c2ccc3c(=O)ccn(-c4ccccc4)c3n2)C1 | F-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]):[c:5](-[F;D1;H0:6]):[c:7].[#7:8]=[C:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-1>>[#7:8]=[C:9]1-[C:10]-[C:11]-[N;H0;D3;+0:12](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]):[c:5](-[F;D1;H0:6]):[c:7])-[C:13]-1 | 81 | [{"value": 81.0, "product": "NCC1CN(CC1=NOC(C)(C)C)C1=C(C=C2C(C(=CN(C2=N1)C1=C(C=C(C=C1)F)F)C(=O)O)=O)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.6, "product": "NCC1CN(CC1=NOC(C)(C)C)C1=C(C=C2C(C(=CN(C2=N1)C1=C(C=C(C=C1)F)F)C(=O)O)=O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | 168 mg (0.5 mmole) of 6,7-difluoro-1-(2,4-difluorophenyl)-4-oxo-1,4-dihydro-naphthyridine-3-carboxylic acid and 143 mg (0.55 mmole) of 3-aminomethyl-4-t-butyloxyiminopyrrolidine dihydrochloride were suspended in 3 ml of dry acetonitrile. Then, 230 mg (1.5 mmole) of 1,8-diazabicyclo[5.4.0]undec-7-ene was added thereto, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1cnc2ncccc2c1 | C1CC[NH]C1.c1cnc2ncccc2c1 | C1CC[NH]C1.c1cnc2ncccc2c1.c1ccccc1 | HF | C(C)#N | null | 0.25 | CC(C)(C)ON=C1CNCC1CN.O=C(O)c1cn(-c2ccc(F)cc2F)c2nc(F)c(F)cc2c1=O>C(C)#N>CC(C)(C)ON=C1CN(c2nc3c(cc2F)c(=O)c(C(=O)O)cn3-c2ccc(F)cc2F)CC1CN |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ab5a462bd8504edf8a49db2e10bfe37a | CC(=O)OC1C=CC(=O)N2CC(OC(C)=O)C(OC(C)=O)C12>>CC(=O)O[C@H]1[C@H]2[C@H](OC(C)=O)CCC(O)N2C[C@H]1OC(C)=O | CC(=O)OC1CN2C(C1OC(=O)C)C(C=CC2=O)OC(=O)C.[H][H]>>CC(=O)O[C@@H]1CCC(N2[C@H]1[C@@H]([C@@H](C2)OC(=O)C)OC(=O)C)O | [CH3:1][C:2](=[O:3])[O:4][CH:5]1[CH:6]2[CH:7]([O:8][C:9]([CH3:10])=[O:11])[CH:12]=[CH:13][C:14](=[O:15])[N:16]2[CH2:17][CH:18]1[O:19][C:20]([CH3:21])=[O:22]>>[CH3:1][C:2](=[O:3])[O:4][C@H:5]1[C@H:6]2[C@H:7]([O:8][C:9]([CH3:10])=[O:11])[CH2:12][CH2:13][CH:14]([OH:15])[N:16]2[CH2:17][C@H:18]1[O:19][C:20]([CH3:21])=[O:22] | CC(=O)OC1C=CC(=O)N2CC(OC(C)=O)C(OC(C)=O)C12 | CC(=O)O[C@H]1[C@H]2[C@H](OC(C)=O)CCC(O)N2C[C@H]1OC(C)=O | null | null | C(C)O | Reduction | OtherReaction | fd7d2ac66486e4134b1977aca077072436e99a7c66f4ea7b4894a8b071b7b77a | a482d04f40c78ee77b2bb7ee1ddd81c55502fc86accd776e8e7cf5fc57b56aa1 | C1CCN2CCC[C@H]2C1 | [C:1]-[#7:2]1-[C:3](-[C:4])-[CH;D3;+0:5](-[#8:6]-[C:7](-[C;D1;H3:8])=[O;D1;H0:9])-[CH;D2;+0:10]=[CH;D2;+0:11]-[C;H0;D3;+0:12]-1=[O;H0;D1;+0:13]>>[C:1]-[#7:2]1-[C:3](-[C:4])-[C@H;D3;+0:5](-[#8:6]-[C:7](-[C;D1;H3:8])=[O;D1;H0:9])-[CH2;D2;+0:10]-[CH2;D2;+0:11]-[CH;D3;+0:12]-1-[OH;D1;+0:13] | null | [] | null | null | 8 | HOUR | (1S,2R,8R,8aR)-1,2,8-triacetoxy-1,2,3,5,8,8a-hexahydro-5-oxyindolizine, 13, 22 g (0.070 mole), was hydrogenated at atmospheric pressure of hydrogen in 400 mL ethanol containing 3 g 10% Pd on carbon. The reaction was allowed to proceed overnight. The catalyst was filtered, and the filtrate was evaporated to dryness. The... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Secondary alcohol | C1=CCN2CCCC2C1 | C1CCN2CCC[C@H]2C1 | C1CCN2CCC[C@H]2C1 | null | C(C)O | null | 8 | CC(=O)OC1C=CC(=O)N2CC(OC(C)=O)C(OC(C)=O)C12>C(C)O>CC(=O)O[C@H]1[C@H]2[C@H](OC(C)=O)CCC(O)N2C[C@H]1OC(C)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e7bfc3a61b0e49e0b569fa6da8eab9c5 | CCOP(=O)(CC(=O)N[C@]1(OCc2ccccc2)O[C@H](C)[C@@H](OC(C)=O)C[C@@H]1OC(C)=O)OCC>>CCOP(=O)(CC(=O)NC1(O)O[C@H](C)[C@@H](OC(C)=O)C[C@@H]1OC(C)=O)OCC | C(C)(=O)O[C@@H]1[C@@](OCC2=CC=CC=C2)(O[C@@H]([C@H](C1)OC(C)=O)C)NC(CP(=O)(OCC)OCC)=O.C(C)O>>C(C)(=O)O[C@@H]1C(O)(O[C@@H]([C@H](C1)OC(C)=O)C)NC(CP(=O)(OCC)OCC)=O | c1ccc(C[O:11][C@@:10]2([NH:9][C:7]([CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:26][CH2:27][CH3:28])=[O:8])[O:12][C@H:13]([CH3:14])[C@@H:15]([O:16][C:17]([CH3:18])=[O:19])[CH2:20][C@@H:21]2[O:22][C:23]([CH3:24])=[O:25])cc1>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][C:7](=[O:8])[NH:9][C:10]1([OH:11])[O:12][C@H:13]([CH3:14... | CCOP(=O)(CC(=O)N[C@]1(OCc2ccccc2)O[C@H](C)[C@@H](OC(C)=O)C[C@@H]1OC(C)=O)OCC | CCOP(=O)(CC(=O)NC1(O)O[C@H](C)[C@@H](OC(C)=O)C[C@@H]1OC(C)=O)OCC | null | [Pd] | C(=O)O | Deprotection | Hydroxyl benzyl deprotection | 3519c572d4cdc6e4492ddc62371f633ac7f142ee47bb7da6e4a9f9b5cd5ff2d0 | 3e1943ba4c0a89acd871c6a988bf0e8edc398f81f37331b79618b2411f80cd6d | C1CCOCC1 | [C:1]-[#8:2]-[C@;H0;D4;+0:3](-[#7:4]-[C:5](-[C:6])=[O;D1;H0:7])(-[O;H0;D2;+0:8]-C-c1:c:c:c:c:c:1)-[C:9](-[#8:10]-[C:11](-[C;D1;H3:12])=[O;D1;H0:13])-[C:14]>>[C:1]-[#8:2]-[C;H0;D4;+0:3](-[OH;D1;+0:8])(-[#7:4]-[C:5](-[C:6])=[O;D1;H0:7])-[C:9](-[#8:10]-[C:11](-[C;D1;H3:12])=[O;D1;H0:13])-[C:14] | null | [] | null | null | null | null | Crude benzyl 2,4-di-O-acetyl-3,6-dideoxydiethylphosphonoacetamido-alpha-D-mannopyranoside, 21, ethanol (10 ml), 2 88% formic acid and 0.1 g Pd black were heated at reflux overnight under argon with stirring. The reaction mixture was filtered and evaporated to dryness, and the residue was chromatographed on SiO2 (40 g; ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Tertiary alcohol | c1ccccc1 | null | C1CCOCC1 | Other | [Pd].C(=O)O | null | null | CCOP(=O)(CC(=O)N[C@]1(OCc2ccccc2)O[C@H](C)[C@@H](OC(C)=O)C[C@@H]1OC(C)=O)OCC>[Pd].C(=O)O>CCOP(=O)(CC(=O)NC1(O)O[C@H](C)[C@@H](OC(C)=O)C[C@@H]1OC(C)=O)OCC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1c6e0a0c6762481f8f0b8e21fe0e5b9e | COC(=O)CCC[N+](=O)[O-].O=Cc1ccccc1.[NH4+]>>O=C1CC[C@@H]([N+](=O)[O-])[C@H](c2ccccc2)N1 | [N+](=O)([O-])CCCC(=O)OC.C(C1=CC=CC=C1)=O.C(C)(=O)[O-].[NH4+]>>[N+](=O)([O-])[C@H]1[C@@H](NC(CC1)=O)C1=CC=CC=C1 | CO[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][N+:6](=[O:7])[O-:8].O=[CH:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[NH4+:16]>>[O:1]=[C:2]1[CH2:3][CH2:4][C@@H:5]([N+:6](=[O:7])[O-:8])[C@H:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[NH:16]1 | COC(=O)CCC[N+](=O)[O-].O=Cc1ccccc1.[NH4+] | O=C1CC[C@@H]([N+](=O)[O-])[C@H](c2ccccc2)N1 | null | null | C(C)O | Acylation | OtherReaction | 9402e7d2d4a11355b869c0e5053e69e7a49790dcc5ec49c913047b2193486448 | 62e08fd83e95abe9caffb690356f76bd7ee08d6cde6d54358808c23fd2777059 | O=C1CCC[C@H](c2ccccc2)N1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[CH2;D2;+0:5]-[#7;+:6](-[O;-;D1;H0:7])=[O;D1;H0:8].O=[CH;D2;+0:9]-[c:10](:[c:11]):[c:12].[NH4+;D0:13]>>[O;-;D1;H0:7]-[#7;+:6](=[O;D1;H0:8])-[C@@H;D3;+0:5]1-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:13]-[C@H;D3;+0:9]-1-[c:10](:[c:11]):[c:12] | 85 | [{"value": 85.0, "product": "[N+](=O)([O-])[C@H]1[C@@H](NC(CC1)=O)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.7, "product": "[N+](=O)([O-])[C@H]1[C@@H](NC(CC1)=O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Methyl 4-nitrobutyrate (1) (240 g, 1.63 mol), benzaldehyde (189 g, 1.78 mol), ammonium acetate (164 g, 2.12 mol) and ethanol (1680 ml) were placed in a 3-liter 3-necked flask equipped with a mechanical stirrer, under an atmosphere of nitrogen. The mixture was heated under reflux for four hours to yield an orange soluti... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester.Nitro group | Nitro group.Secondary amide | null | C1CCNCC1 | C1CCNCC1.c1ccccc1 | HO- | C(C)O | null | null | COC(=O)CCC[N+](=O)[O-].O=Cc1ccccc1.[NH4+]>C(C)O>O=C1CC[C@@H]([N+](=O)[O-])[C@H](c2ccccc2)N1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-00e070c838c440f296400559ff44fce7 | O=C1CC[C@@H]([N+](=O)[O-])[C@H](c2ccccc2)N1>>O=C1CCC(=O)C(c2ccccc2)N1 | CSC.[N+](=O)([O-])[C@H]1[C@@H](NC(CC1)=O)C1=CC=CC=C1.ClCCl.CC(C)([O-])C.[K+]>>O=C1NC(C(CC1)=O)C1=CC=CC=C1 | [O-][N+]([C@@H:5]1[CH2:4][CH2:3][C:2](=[O:1])[NH:14][C@H:7]1[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)=[O:6]>>[O:1]=[C:2]1[CH2:3][CH2:4][C:5](=[O:6])[CH:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[NH:14]1 | O=C1CC[C@@H]([N+](=O)[O-])[C@H](c2ccccc2)N1 | O=C1CCC(=O)C(c2ccccc2)N1 | null | null | CO | Functional Group Interconversion | Nef reaction (nitro to ketone) | 58f95b2144f0a380427d8f8bfa00aef5a7a50ae0b82878d96b22dc91477827d9 | 1df445eca91b47d301fc1478044e1cd6fb16a038e33213021748ecbc6ef69082 | O=C1CCC(=O)C(c2ccccc2)N1 | [O-]-[N+](=[O;H0;D1;+0:1])-[C@@H;D3;+0:2]1-[C:3]-[C:4]-[C:5](=[O;D1;H0:6])-[#7:7]-[C@H;D3;+0:8]-1-[c:9](:[c:10]):[c:11]>>[O;D1;H0:6]=[C:5]1-[#7:7]-[CH;D3;+0:8](-[c:9](:[c:10]):[c:11])-[C;H0;D3;+0:2](=[O;H0;D1;+0:1])-[C:3]-[C:4]-1 | 78.4 | [{"value": 78.0, "product": "O=C1NC(C(CC1)=O)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.4, "product": "O=C1NC(C(CC1)=O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | trans-3 -Nitro-6-oxo-2-phenylpiperidine (80 g, 0.364 mol) was suspended in methanol:dichloromethane (Example 1a, 1:1, 500 ml) under nitrogen. The suspension was cooled to 0° C. and potassium t-butoxide (44.8 g, 0.4 mol) was added in portions over 30 mins. The cooling bath was then removed and the solution stirred for a... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Ketone | C1CCNCC1 | C1CCNCC1 | C1CCNCC1.c1ccccc1 | HO- | CO | 0 | 0.25 | O=C1CC[C@@H]([N+](=O)[O-])[C@H](c2ccccc2)N1>CO>O=C1CCC(=O)C(c2ccccc2)N1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5f52b1beaf2f4650a80696f1a265442e | O=C1CC[C@@H]([N+](=O)[O-])[C@H](c2ccccc2)N1>>O=C1CCC(=O)C(c2ccccc2)N1 | [N+](=O)([O-])[C@H]1[C@@H](NC(CC1)=O)C1=CC=CC=C1.C[O-].[Na+].C(C)(=O)[O-].[NH4+].Cl>>O=C1NC(C(CC1)=O)C1=CC=CC=C1 | [O-][N+]([C@@H:5]1[CH2:4][CH2:3][C:2](=[O:1])[NH:14][C@H:7]1[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)=[O:6]>>[O:1]=[C:2]1[CH2:3][CH2:4][C:5](=[O:6])[CH:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[NH:14]1 | O=C1CC[C@@H]([N+](=O)[O-])[C@H](c2ccccc2)N1 | O=C1CCC(=O)C(c2ccccc2)N1 | null | [Cl-].[Cl-].[Cl-].[Ti+3] | O.CO | Functional Group Interconversion | Nef reaction (nitro to ketone) | 58f95b2144f0a380427d8f8bfa00aef5a7a50ae0b82878d96b22dc91477827d9 | 1df445eca91b47d301fc1478044e1cd6fb16a038e33213021748ecbc6ef69082 | O=C1CCC(=O)C(c2ccccc2)N1 | [O-]-[N+](=[O;H0;D1;+0:1])-[C@@H;D3;+0:2]1-[C:3]-[C:4]-[C:5](=[O;D1;H0:6])-[#7:7]-[C@H;D3;+0:8]-1-[c:9](:[c:10]):[c:11]>>[O;D1;H0:6]=[C:5]1-[#7:7]-[CH;D3;+0:8](-[c:9](:[c:10]):[c:11])-[C;H0;D3;+0:2](=[O;H0;D1;+0:1])-[C:3]-[C:4]-1 | 75 | [{"value": 75.0, "product": "O=C1NC(C(CC1)=O)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | To a 5L flask containing ammonium acetate (450g) which had been thoroughly purged with nitrogen was added a freshly prepared solution of titanium trichloride (300 g, 1.95 mol) in deoxygenated water (2.1L) with ice-bath cooling. To the resulting green solution was added a solution of trans-3-nitro-6-oxo-2-phenylpiperidi... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Ketone | C1CCNCC1 | C1CCNCC1 | C1CCNCC1.c1ccccc1 | HO- | [Cl-].[Cl-].[Cl-].[Ti+3].O.CO | 0 | 1 | O=C1CC[C@@H]([N+](=O)[O-])[C@H](c2ccccc2)N1>[Cl-].[Cl-].[Cl-].[Ti+3].O.CO>O=C1CCC(=O)C(c2ccccc2)N1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a53056ad25d944aab213571494808620 | BrP(Br)Br.CC(O)c1cc(C(F)(F)F)cc(C(F)(F)F)c1>>CC(Br)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | FC(C=1C=C(C=C(C1)C(F)(F)F)C(C)O)(F)F.P(Br)(Br)Br>>FC(C=1C=C(C=C(C1)C(F)(F)F)C(C)Br)(F)F | BrP(Br)[Br:3].O[CH:2]([CH3:1])[c:4]1[cH:5][c:6]([C:7]([F:8])([F:9])[F:10])[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17]1>>[CH3:1][CH:2]([Br:3])[c:4]1[cH:5][c:6]([C:7]([F:8])([F:9])[F:10])[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17]1 | BrP(Br)Br.CC(O)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | CC(Br)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | null | null | O | Functional Group Interconversion | OtherReaction | ed0947fcf0a870fa4568d74e29e264525d0acf781c20c116470537e8cf1d911a | 495868b18ac37eabad313a8861412e57f019fb3569a2b2e50afa3ee29413ec02 | c1ccccc1 | Br-P(-Br)-[Br;H0;D1;+0:1].O-[CH;D3;+0:2](-[C;D1;H3:3])-[c:4](:[c:5]):[c:6]>>[Br;H0;D1;+0:1]-[CH;D3;+0:2](-[C;D1;H3:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 30 | MINUTE | To 1-(3,5-bis(trifiuoromethyl)phenyl)-1-hydroxyethane (10 g) was added phosphorous tribromide (3.7 ml) to give a clear solution. After 30 minutes the solution was added to water (300 ml) and the solution stirred for a further 30 minutes. Petroleum ether bp=60°-80° C. was added and the organic solution washed with water... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Secondary halide | null | null | c1ccccc1 | HBr | O | null | 0.5 | BrP(Br)Br.CC(O)c1cc(C(F)(F)F)cc(C(F)(F)F)c1>O>CC(Br)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6c6600010a194ad1a86936c8f6fa6879 | CC(C)(C)OC(=O)Cl.CC(C)(C)OC(=O)OC(C)(C)C>>CC(C)(C)OC(=O)OC(=O)OC(C)(C)C | Cl[C].CCOCC.C(C)(C)(C)OC(OC(C)(C)C)=O.C(C)(C)(C)OC(=O)Cl.N1=C(C=CC=C1C)C>>C(C)(C)(C)OC(=O)OC(=O)OC(C)(C)C | Cl[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].CC(C)(C)[O:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[O:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15] | CC(C)(C)OC(=O)Cl.CC(C)(C)OC(=O)OC(C)(C)C | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C | null | null | ClCCl.C(C)N(CC)CC.N1=CC=CC=C1 | Protection | OtherReaction | 0f666e2e9239bc3e2b469a8e6062825157731d14d98b0ae40fe57e890a7f8e37 | 3d5405115c494df9df63719b7f19d67772b344737e1bdbee4bdc791922d38baa | null | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].Cl-[C;H0;D3;+0:9](=[O;D1;H0:10])-[#8:11]-[C:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[C;D1;H3:15]>>[C;D1;H3:6]-[C:5](-[C;D1;H3:7])(-[C;D1;H3:8])-[#8:4]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:1]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[#8:11]-[C... | null | [] | null | null | null | null | The 3-(N-t-butyloxycarbonyl-1'-N-methylaminoethyl)pyrrolidines (60, 61, 62, 63) were prepared by reacting the amines (8-11) with a t-butyloxycarbonyl transfer agent such as di-t-butylcarbonate or t-butyloxycarbonyl chloride or the like in the presence of an acid scavenger such as a tertiary amine including pyridine, lu... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carbonic Ester.Ether.Boc.Boc | Anhydride | null | null | null | HCl | ClCCl.C(C)N(CC)CC.N1=CC=CC=C1 | null | null | CC(C)(C)OC(=O)Cl.CC(C)(C)OC(=O)OC(C)(C)C>ClCCl.C(C)N(CC)CC.N1=CC=CC=C1>CC(C)(C)OC(=O)OC(=O)OC(C)(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-27ebac39e364439fa985f8a3d3eef3c5 | CCOC(=O)Cc1ccc2ccccc2c1>>OCCNc1ccc2ccccc2c1 | C(C)(=O)O.[O-]CC.[Na+].C1=C(C=CC2=CC=CC=C12)CC(=O)OCC.N(=O)OCCCC>>C1=C(C=CC2=CC=CC=C12)NCCO | CCO[C:2](=[O:1])[CH2:3][c:5]1[cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[cH:14]1>>[OH:1][CH2:2][CH2:3][NH:4][c:5]1[cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[cH:14]1 | CCOC(=O)Cc1ccc2ccccc2c1 | OCCNc1ccc2ccccc2c1 | null | null | C(C)O | Miscellaneous | OtherReaction | baeafa7edc6df17a9d354abb8db9c29baad492dff3d8ef81d31d4184fc5c2c7e | bac4e04d71d5e57ebfb9a4ae4320481a6b98c6289a76c30e38737cd8f725e5e2 | c1ccc2ccccc2c1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH2;D2;+0:3]-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[CH2;D2;+0:3]-[#7:9]-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8] | null | [] | 23 | CELSIUS | 18 | HOUR | Ethyl 2-naphthylacetate (11.6 g) was dissolved in ethanol (100 mL) and treated with solid sodium ethoxide (3.5 g) and then dropwise with n-butyl nitrite (7.6 mL). The reaction was stirred at 23° C. for 18 h and treated with acetic acid (5 mL) and stirred for 1 h. The ethanol was removed under reduced pressure and the r... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol.Secondary amine | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | HO- | C(C)O | 23 | 18 | CCOC(=O)Cc1ccc2ccccc2c1>C(C)O>OCCNc1ccc2ccccc2c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e6135515d659427a98f0b27e43c85d8b | NC(=O)c1c(F)cccc1F.O=CC(=O)O>>O=C(NC(O)C(=O)O)c1c(F)cccc1F | FC1=C(C(=O)N)C(=CC=C1)F.O.C(C=O)(=O)O>>FC1=C(C(=O)NC(C(=O)O)O)C(=CC=C1)F | [O:1]=[C:2]([NH2:3])[c:9]1[c:10]([F:11])[cH:12][cH:13][cH:14][c:15]1[F:16].[CH:4](=[O:5])[C:6](=[O:7])[OH:8]>>[O:1]=[C:2]([NH:3][CH:4]([OH:5])[C:6](=[O:7])[OH:8])[c:9]1[c:10]([F:11])[cH:12][cH:13][cH:14][c:15]1[F:16] | NC(=O)c1c(F)cccc1F.O=CC(=O)O | O=C(NC(O)C(=O)O)c1c(F)cccc1F | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 4a3b52c650544f6bcd441fa95d4d2ff87dd9c739061ff39332928c46df320b3d | b10a3ef220ace1bf1449d6e4f07e4fab45c01f4bc98efc71f34b015ef2e7ec16 | c1ccccc1 | [NH2;D1;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[O;D1;H0:5]=[C:6](-[O;D1;H1:7])-[CH;D2;+0:8]=[O;H0;D1;+0:9]>>[O;D1;H0:3]=[C:2](-[c:4])-[NH;D2;+0:1]-[CH;D3;+0:8](-[OH;D1;+0:9])-[C:6](=[O;D1;H0:5])-[O;D1;H1:7] | 52.5 | [{"value": 52.5, "product": "FC1=C(C(=O)NC(C(=O)O)O)C(=CC=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 50 g (0.318 mol) of 2,6-difluorobenzamide, 32 g (0.349 mol) of glyoxylic acid monohydrate and 200 mL of acetone was refluxed for 5 h. The reaction was cooled and solvents evaporated to give a white solid. It was triturated with cold acetone to afford 38.56 g of a white solid: mp 125°-127° C. 1H-NMR (DMSO-d... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amide | Secondary amide.Secondary alcohol | null | null | c1ccccc1 | null | CC(=O)C | null | null | NC(=O)c1c(F)cccc1F.O=CC(=O)O>CC(=O)C>O=C(NC(O)C(=O)O)c1c(F)cccc1F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5979ac0adc0b4a1b9ea3a8531e33ee0d | Brc1cccs1.O=C(NC(O)C(=O)O)c1c(F)cccc1F>>O=C(NC(C(=O)O)c1ccc(Br)s1)c1c(F)cccc1F | FC1=C(C(=O)NC(C(=O)O)O)C(=CC=C1)F.BrC=1SC=CC1>>BrC1=CC=C(S1)C(C(=O)O)NC(C1=C(C=CC=C1F)F)=O | [cH:8]1[cH:9][cH:10][c:11]([Br:12])[s:13]1.O[CH:4]([NH:3][C:2](=[O:1])[c:14]1[c:15]([F:16])[cH:17][cH:18][cH:19][c:20]1[F:21])[C:5](=[O:6])[OH:7]>>[O:1]=[C:2]([NH:3][CH:4]([C:5](=[O:6])[OH:7])[c:8]1[cH:9][cH:10][c:11]([Br:12])[s:13]1)[c:14]1[c:15]([F:16])[cH:17][cH:18][cH:19][c:20]1[F:21] | Brc1cccs1.O=C(NC(O)C(=O)O)c1c(F)cccc1F | O=C(NC(C(=O)O)c1ccc(Br)s1)c1c(F)cccc1F | null | null | CS(=O)(=O)O | C-C Coupling | OtherReaction | ad96d5c2435232f883a245478104e1a9fc7c62cf0caf6a785ca127030f4f3fa0 | 7ccf8a4ec454d6cc03ce1e3efafa301b3c51d9e9635279e99312f4bc816939b8 | O=C(NCc1cccs1)c1ccccc1 | O-[CH;D3;+0:1](-[#7:2]-[C:3](=[O;D1;H0:4])-[c:5])-[C:6](=[O;D1;H0:7])-[O;D1;H1:8].[#16;a:9]1:[c:10]:[c:11]:[c:12]:[cH;D2;+0:13]:1>>[O;D1;H0:4]=[C:3](-[c:5])-[#7:2]-[CH;D3;+0:1](-[C:6](=[O;D1;H0:7])-[O;D1;H1:8])-[c;H0;D3;+0:13]1:[#16;a:9]:[c:10]:[c:11]:[c:12]:1 | 52.3 | [{"value": 52.3, "product": "BrC1=CC=C(S1)C(C(=O)O)NC(C1=C(C=CC=C1F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4.76 g (20.6 mmol) of the product of Step A in 140 mL of methanesulfonic acid was immersed in an ice-water bath (temperature between 5°-10° C.). Then, 4.0 g (24.6 mmol) of 2-bromothiophene was added dropwise. It was stirred at the same temperature until a deep blue-black color formed. It was poured into i... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | c1ccsc1 | c1ccsc1 | c1ccsc1.c1ccccc1 | HO- | CS(=O)(=O)O | null | null | Brc1cccs1.O=C(NC(O)C(=O)O)c1c(F)cccc1F>CS(=O)(=O)O>O=C(NC(C(=O)O)c1ccc(Br)s1)c1c(F)cccc1F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5bd00e53bfe843f9897be04b64fe95ed | CO.O=C(NC(C(=O)O)c1ccc(Br)s1)c1c(F)cccc1F>>COC(=O)C(NC(=O)c1c(F)cccc1F)c1ccc(Br)s1 | BrC1=CC=C(S1)C(C(=O)O)NC(C1=C(C=CC=C1F)F)=O.CO.S(=O)(Cl)Cl>>BrC1=CC=C(S1)C(C(=O)OC)NC(C1=C(C=CC=C1F)F)=O | [CH3:1][OH:2].O[C:3](=[O:4])[CH:5]([NH:6][C:7](=[O:8])[c:9]1[c:10]([F:11])[cH:12][cH:13][cH:14][c:15]1[F:16])[c:17]1[cH:18][cH:19][c:20]([Br:21])[s:22]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([NH:6][C:7](=[O:8])[c:9]1[c:10]([F:11])[cH:12][cH:13][cH:14][c:15]1[F:16])[c:17]1[cH:18][cH:19][c:20]([Br:21])[s:22]1 | CO.O=C(NC(C(=O)O)c1ccc(Br)s1)c1c(F)cccc1F | COC(=O)C(NC(=O)c1c(F)cccc1F)c1ccc(Br)s1 | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | O=C(NCc1cccs1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[#7:4]-[C:5]=[O;D1;H0:6])-[c:7]:[#16;a:8].[C;D1;H3:9]-[OH;D1;+0:10]>>[#16;a:8]:[c:7]-[C:3](-[#7:4]-[C:5]=[O;D1;H0:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:10]-[C;D1;H3:9] | null | [] | null | null | null | null | An amount of 3.415 g (9 mmol) of the product of Step B was dissolved in 19 mL of methanol. It was cooled in an ice-bath and 1.13 mL of thionyl chloride was added dropwise. The mixture was heated at reflux for 30 min. It was cooled and the methanol removed under reduced pressure. A saturated solution of sodium bicarbona... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1.c1ccsc1 | HO- | null | null | null | CO.O=C(NC(C(=O)O)c1ccc(Br)s1)c1c(F)cccc1F>>COC(=O)C(NC(=O)c1c(F)cccc1F)c1ccc(Br)s1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f7ff2b7c98a8486da666ddbb8f451938 | Fc1cccc(F)c1C1=NC(c2ccc(Br)s2)CO1.OB(O)c1ccccc1>>Fc1cccc(F)c1C1=NC(c2ccc(-c3ccccc3)s2)CO1 | BrC1=CC=C(S1)C1N=C(OC1)C1=C(C=CC=C1F)F.C([O-])([O-])=O.[Na+].[Na+].C1(=CC=CC=C1)B(O)O>>FC1=C(C(=CC=C1)F)C=1OCC(N1)C=1SC(=CC1)C1=CC=CC=C1 | Br[c:15]1[cH:14][cH:13][c:12]([CH:11]2[N:10]=[C:9]([c:8]3[c:2]([F:1])[cH:3][cH:4][cH:5][c:6]3[F:7])[O:24][CH2:23]2)[s:22]1.OB(O)[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([F:7])[c:8]1[C:9]1=[N:10][CH:11]([c:12]2[cH:13][cH:14][c:15](-[c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[s:22]... | Fc1cccc(F)c1C1=NC(c2ccc(Br)s2)CO1.OB(O)c1ccccc1 | Fc1cccc(F)c1C1=NC(c2ccc(-c3ccccc3)s2)CO1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1(=CC=CC=C1)C.CO | C-C Coupling | Suzuki coupling with boronic acids | a9e750b5cb26673fc488a731642519fa5963d6a2e4d2eeb976470c7f17606def | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(C2=NC(c3ccc(-c4ccccc4)s3)CO2)cc1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1.O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1):[c:9]:[c:10] | 83 | [{"value": 83.0, "product": "FC1=C(C(=CC=C1)F)C=1OCC(N1)C=1SC(=CC1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 2 | HOUR | To a solution of 100 mg (0.3 mmol) of the product of Step D of Example 2 in 0.6 mL toluene was added successively 10.4 mg (0.009 mmol) of Pd (PPh3)4, 0.3 mL of 2.0 m sodium carbonate, and 44 mg (0.36 mmol) of phenylboronic acid in 0.15 mL of methanol. The mixture was stirred at 80° C. for 2 h. It was cooled and partiti... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccsc1.c1ccccc1 | c1ccsc1.c1ccccc1 | c1ccccc1.C1=NCCO1.c1ccsc1.c1ccccc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C.CO | 80 | 2 | Fc1cccc(F)c1C1=NC(c2ccc(Br)s2)CO1.OB(O)c1ccccc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C.CO>Fc1cccc(F)c1C1=NC(c2ccc(-c3ccccc3)s2)CO1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-29a7c6ca98d34ee2a5aada83fa10f22d | CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3ccc(=O)cc-3[nH]c2-1>>CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3cc(O)ccc3nc2-1 | C(Cl)(Cl)Cl.CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=C(C3=C2)NC5=CC(=O)C=CC5=C4)O.CO>>CC[C@@]1(C2=C(COC1=O)C(=O)N3CC=4C=C5C=C(C=CC5=NC4C3=C2)O)O | [CH3:1][CH2:2][C@@:3]1([OH:4])[C:5](=[O:6])[O:7][CH2:8][c:9]2[c:10]1[cH:11][c:12]1[n:13]([c:14]2=[O:15])[CH2:16][c:17]2[cH:18][c:19]3[cH:20][cH:21][c:23](=[O:22])[cH:24][c:25]-3[nH:26][c:27]2-1>>[CH3:1][CH2:2][C@@:3]1([OH:4])[C:5](=[O:6])[O:7][CH2:8][c:9]2[c:10]1[cH:11][c:12]1[n:13]([c:14]2=[O:15])[CH2:16][c:17]2[cH:18... | CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3ccc(=O)cc-3[nH]c2-1 | CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3cc(O)ccc3nc2-1 | null | null | FC(C(=O)O)(F)F | Miscellaneous | OtherReaction | b5548fadc146433e9acdf6d786c997613c4f7901c76ad3212d9b86d0ebc399e3 | 6dd67d2d062ecf3a4bfbb86c40e45739a873f777b0585faa974e3874e3a0b559 | O=C1Cc2cc3n(c(=O)c2CO1)Cc1cc2ccccc2nc1-3 | [#7;a:1]:[c:2]-[c:3]1:[c:4]:[c:5]:[c;H0;D3;+0:6]2:[c:7]:[cH;D2;+0:8]:[c;H0;D3;+0:9](=[O;H0;D1;+0:10]):[c:11]:[c;H0;D3;+0:12]-2:[nH;D2;+0:13]:1>>[#7;a:1]:[c:2]-[c:3]1:[c:4]:[c:5]:[c;H0;D3;+0:6]2:[c:7]:[c;H0;D3;+0:8](-[OH;D1;+0:10]):[cH;D2;+0:9]:[c:11]:[c;H0;D3;+0:12]:2:[n;H0;D2;+0:13]:1 | null | [] | null | null | null | null | Naturally available mixture of 10 and 11-hydroxy camptothecin (1.0 g) is dissolved in anhydrous trifluoroacetic acid (5 ml) and anhydrous methanol (10 ml) to form a homogeneous solution of the quaternized components of the mixture. The homogeneous solution is then absorbed over enough silica gel (60A; 60-230 mesh) to f... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic alcohol | C1Cc2cc3c4nc5ccccc5cc4Cn3cc2CO1 | C1Cc2cc3c4nc5ccccc5cc4Cn3cc2CO1 | C1Cc2cc3c4nc5ccccc5cc4Cn3cc2CO1 | null | FC(C(=O)O)(F)F | null | null | CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3ccc(=O)cc-3[nH]c2-1>FC(C(=O)O)(F)F>CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3cc(O)ccc3nc2-1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ce1330cec512459bbd1a23148a42b7c2 | CCC=O.CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3cc(O)ccc3nc2-1>>CCc1c2c(nc3ccc(O)cc13)-c1cc3c(c(=O)n1C2)COC(=O)[C@]3(O)CC | CC[C@@]1(C2=C(COC1=O)C(=O)N3CC=4C=C5C=C(C=CC5=NC4C3=C2)O)O.S(=O)(=O)([O-])OOS(=O)(=O)[O-].[K+].[K+].C(CC)=O.S(O)(O)(=O)=O.FC(C(=O)O)(F)F>>CCC1=C2C=C(C=CC2=NC3=C1CN4C3=CC5=C(C4=O)COC(=O)[C@@]5(CC)O)O | O=C[CH2:2][CH3:1].[cH:3]1[c:4]2[c:5]([n:6][c:7]3[cH:8][cH:9][c:10]([OH:11])[cH:12][c:13]13)-[c:14]1[cH:15][c:16]3[c:17]([c:18](=[O:19])[n:20]1[CH2:21]2)[CH2:22][O:23][C:24](=[O:25])[C@:26]3([OH:27])[CH2:28][CH3:29]>>[CH3:1][CH2:2][c:3]1[c:4]2[c:5]([n:6][c:7]3[cH:8][cH:9][c:10]([OH:11])[cH:12][c:13]13)-[c:14]1[cH:15][c:... | CCC=O.CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3cc(O)ccc3nc2-1 | CCc1c2c(nc3ccc(O)cc13)-c1cc3c(c(=O)n1C2)COC(=O)[C@]3(O)CC | null | O.O.O.O.O.O.O.S(=O)(=O)([O-])[O-].[Fe+2] | O | C-C Coupling | OtherReaction | e086937f9b1b4cd3230ad632fe7c477d59bf1145fa5cb9a64da42851bc68f6ea | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1Cc2cc3n(c(=O)c2CO1)Cc1cc2ccccc2nc1-3 | O=C-[CH2;D2;+0:1]-[C;D1;H3:2].[c:3]:[c:4]1:[cH;D2;+0:5]:[c:6]2:[c:7](:[#7;a:8]:[c:9]:1:[c:10])-[c:11]:[#7;a:12]-[C:13]-2>>[C;D1;H3:2]-[CH2;D2;+0:1]-[c;H0;D3;+0:5]1:[c:4](:[c:3]):[c:9](:[c:10]):[#7;a:8]:[c:7]2:[c:6]:1-[C:13]-[#7;a:12]:[c:11]-2 | null | [] | null | null | 15 | MINUTE | The 10-hydroxy camptothecin (800 mg; 2.2 mmol) is suspended in water (24 ml). Iron (II) sulfate heptahydrate (250 mg, 0.85 millimoles) is added to the suspension and then followed by the addition of propionaldehyde (3 ml). The reaction mixture is then cooled in an ice bath and concentrated sulfuric acid (1 ml) and trif... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | C1Cc2cc3c4nc5ccccc5cc4Cn3cc2CO1 | C1Cc2cc3c4nc5ccccc5cc4Cn3cc2CO1 | C1Cc2cc3c4nc5ccccc5cc4Cn3cc2CO1 | HO- | O.O.O.O.O.O.O.S(=O)(=O)([O-])[O-].[Fe+2].O | null | 0.25 | CCC=O.CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3cc(O)ccc3nc2-1>O.O.O.O.O.O.O.S(=O)(=O)([O-])[O-].[Fe+2].O>CCc1c2c(nc3ccc(O)cc13)-c1cc3c(c(=O)n1C2)COC(=O)[C@]3(O)CC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d58c7e03f08a4b1398a99627fe4be9d6 | CC(C)(C)OC(=O)[C@@H]1CSC(C2CCCCC2)N1C(=O)CNC(=O)Nc1cccc(CC(=O)OCc2ccccc2)c1>>CC(C)(C)OC(=O)[C@@H]1CSC(C2CCCCC2)N1C(=O)CNC(=O)Nc1cccc(CC(=O)O)c1 | CO.C(C)(C)(C)OC(=O)[C@H]1N(C(SC1)C1CCCCC1)C(CNC(NC=1C=C(C=CC1)CC(=O)OCC1=CC=CC=C1)=O)=O.C(=O)[O-].[NH4+]>>C(C)(C)(C)OC(=O)[C@H]1N(C(SC1)C1CCCCC1)C(CNC(NC=1C=C(C=CC1)CC(=O)O)=O)=O | c1ccc(C[O:34][C:32]([CH2:31][c:30]2[cH:29][cH:28][cH:27][c:26]([NH:25][C:23]([NH:22][CH2:21][C:19]([N:18]3[C@H:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][S:10][CH:11]3[CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]3)=[O:20])=[O:24])[cH:35]2)=[O:33])cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])... | CC(C)(C)OC(=O)[C@@H]1CSC(C2CCCCC2)N1C(=O)CNC(=O)Nc1cccc(CC(=O)OCc2ccccc2)c1 | CC(C)(C)OC(=O)[C@@H]1CSC(C2CCCCC2)N1C(=O)CNC(=O)Nc1cccc(CC(=O)O)c1 | null | [Pd] | [OH-].[Na+] | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(NCC(=O)N1CCSC1C1CCCCC1)Nc1ccccc1 | [C:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1>>[C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4] | 58.9 | [{"value": 58.9, "product": "C(C)(C)(C)OC(=O)[C@H]1N(C(SC1)C1CCCCC1)C(CNC(NC=1C=C(C=CC1)CC(=O)O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | null | null | 30 cm3 of methanol are added slowly under an inert atmosphere into a round-bottomed flask containing 2.0 g of benzyl (4R) -3-{3- [2- (4-tert-butoxycarbonyl-2-cyclohexyl-3-thiazolidinyl)-2-oxoethyl]-ureido}phenyl-acetate (isomer A), 1.7 g of ammonium formate and 2.0 g of palladium on charcoal (10% Pd). The reaction medi... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | C1CSC[NH]1.C1CCCCC1.c1ccccc1 | Other | [Pd].[OH-].[Na+] | 25 | null | CC(C)(C)OC(=O)[C@@H]1CSC(C2CCCCC2)N1C(=O)CNC(=O)Nc1cccc(CC(=O)OCc2ccccc2)c1>[Pd].[OH-].[Na+]>CC(C)(C)OC(=O)[C@@H]1CSC(C2CCCCC2)N1C(=O)CNC(=O)Nc1cccc(CC(=O)O)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1643f581587c4ecfa782be2eff73af28 | CC(C)(C)OC(=O)NCC(=O)N1C(Cc2ccccc2)SC[C@H]1C(=O)OC(C)(C)C.CC(C)(C)OC(=O)NCC(=O)O>>CC(C)(C)OC(=O)C(N)C(=O)N1C(Cc2ccccc2)SC[C@H]1C(=O)OC(C)(C)C | C1(CCCCC1)N=C=NC1CCCCC1.C(C)(C)(C)OC(=O)NCC(=O)N1C(SC[C@H]1C(=O)OC(C)(C)C)CC1=CC=CC=C1.C(C1=CC=CC=C1)C1SC[C@H](N1)C(=O)OC(C)(C)C.C(C)(C)(C)OC(=O)NCC(=O)O>>C(C)(C)(C)OC(=O)C(C(=O)N1C(SC[C@H]1C(=O)OC(C)(C)C)CC1=CC=CC=C1)N | O=C(O[C:2]([CH3:1])([CH3:3])[CH3:4])[NH:9][CH2:8][C:10](=[O:11])[N:12]1[CH:13]([CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[S:21][CH2:22][C@H:23]1[C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30].CC(C)(C)OC(=O)NC[C:6]([OH:5])=[O:7]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH:8]([NH2:9])[C:10](=[O... | CC(C)(C)OC(=O)NCC(=O)N1C(Cc2ccccc2)SC[C@H]1C(=O)OC(C)(C)C.CC(C)(C)OC(=O)NCC(=O)O | CC(C)(C)OC(=O)C(N)C(=O)N1C(Cc2ccccc2)SC[C@H]1C(=O)OC(C)(C)C | null | null | null | C-C Coupling | OtherReaction | 452c5a4ab0a68e596ed59dbcfcc8c9f944cf2a36a8b48984f7cf3afa8883abf6 | d4a1a313373c0e4ca1d53b8624833769c1dcf8d648c794bf6856bc1390fac38c | c1ccc(CC2NCCS2)cc1 | C-C(-C)(-C)-O-C(=O)-N-C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[OH;D1;+0:3].O=C(-O-[C;H0;D4;+0:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7])-[NH;D2;+0:8]-[CH2;D2;+0:9]-[C:10](=[O;D1;H0:11])-[#7:12](-[C:13]-[#16:14])-[C:15]-[C:16](-[#8:17])=[O;D1;H0:18]>>[#16:14]-[C:13]-[#7:12](-[C:10](=[O;D1;H0:11])-[CH;D3;+0:9](-[NH2;D1;+0:8])-[C... | null | [] | null | null | null | null | B tert-Butyl (4R)-3-(2-tert-butoxycarbonylaminoacetyl)-2-benzyl-4-thiazolidinecarboxylate (isomer A) may be prepared in a manner similar to that described in Example 1C, but starting with 25.7 g of tert-butyl (2RS,4R)-2-benzyl-4-thiazolidinecarboxylate, 13.9 g of 2-tert-butoxycarbonylaminoacetic acid and 16.3 g of N,N'... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Carboxylic acid.Ether.Ether.Boc.Boc | Ester.Primary amine | null | null | C1CSC[NH]1.c1ccccc1 | HO- | null | null | null | CC(C)(C)OC(=O)NCC(=O)N1C(Cc2ccccc2)SC[C@H]1C(=O)OC(C)(C)C.CC(C)(C)OC(=O)NCC(=O)O>>CC(C)(C)OC(=O)C(N)C(=O)N1C(Cc2ccccc2)SC[C@H]1C(=O)OC(C)(C)C |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.