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-02ee2261663048188cf6d85d2cc96e3f | ord-cc6c87b9be304b508b4408d695432fd7 | CC(C)(C)OC(=O)N1CC[N+](C)(CC2=C(C(=O)[O-])N3C(=O)[C@@H](NC(=O)C(=NOCC(=O)O)c4nsc(N)n4)[C@H]3SC2)CC1>>C[N+]1(CC2=C(C(=O)[O-])N3C(=O)[C@@H](NC(=O)C(=NOCC(=O)O)c4nsc(N)n4)[C@H]3SC2)CCNCC1 | C(=O)O.FC(C(=O)O)(F)F.Cl.NC1=NC(=NS1)C(C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C[N+]2(CCN(CC2)C(=O)OC(C)(C)C)C)C(=O)[O-])C1=O)=NOCC(=O)O>>NC1=NC(=NS1)C(C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C[N+]2(CCNCC2)C)C(=O)[O-])C1=O)=NOCC(=O)O | CC(C)(C)OC(=O)[N:34]1[CH2:33][CH2:32][N+:2]([CH3:1])([CH2:3][C:4]2=[C:5]([C:6](=[O:7])[O-:8])[N:9]3[C:10](=[O:11])[C@@H:12]([NH:13][C:14](=[O:15])[C:16](=[N:17][O:18][CH2:19][C:20](=[O:21])[OH:22])[c:23]4[n:24][s:25][c:26]([NH2:27])[n:28]4)[C@H:29]3[S:30][CH2:31]2)[CH2:36][CH2:35]1>>[CH3:1][N+:2]1([CH2:3][C:4]2=[C:5]([... | CC(C)(C)OC(=O)N1CC[N+](C)(CC2=C(C(=O)[O-])N3C(=O)[C@@H](NC(=O)C(=NOCC(=O)O)c4nsc(N)n4)[C@H]3SC2)CC1 | C[N+]1(CC2=C(C(=O)[O-])N3C(=O)[C@@H](NC(=O)C(=NOCC(=O)O)c4nsc(N)n4)[C@H]3SC2)CCNCC1 | null | null | C(C)(=O)OCC | Reduction | Boc amine deprotection | 948da1202b15332e9a720370b2898a983e40f7f79e8dc94eb151be23c601d994 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | N=C(C(=O)N[C@@H]1C(=O)N2C=C(C[NH+]3CCNCC3)CS[C@H]12)c1ncsn1 | 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 | [{"value": 33.0, "product": "NC1=NC(=NS1)C(C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C[N+]2(CCNCC2)C)C(=O)[O-])C1=O)=NOCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To a mixture of formic acid (10 ml) and trifluoroacetic acid (5 ml) was added 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-carboxymethoxyiminoacetamido]-3-(1-methyl-4-tert-butoxycarbonyl-1-piperazinio)methyl-3-cephem-4-carboxylate hydrochloride (syn isomer) (5.7 g) at 20° C. under stirring. The stirring was continued for 1.... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH+]CC[NH]1 | C1C[NH+]CCN1 | C1=CN2CC[C@H]2SC1.c1ncsn1.C1C[NH+]CCN1 | HO- | C(C)(=O)OCC | null | 1.5 | CC(C)(C)OC(=O)N1CC[N+](C)(CC2=C(C(=O)[O-])N3C(=O)[C@@H](NC(=O)C(=NOCC(=O)O)c4nsc(N)n4)[C@H]3SC2)CC1>C(C)(=O)OCC>C[N+]1(CC2=C(C(=O)[O-])N3C(=O)[C@@H](NC(=O)C(=NOCC(=O)O)c4nsc(N)n4)[C@H]3SC2)CCNCC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6f6c5d046c9e4fcab21226b8290da43a | CN1CCN(C(=O)OC(C)(C)C)CC1.CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(CCl)CS[C@H]12)c1nsc(N)n1>>CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCNCC3)CS[C@H]12)c1nsc(N)n1 | C(C)(=O)OCC.FC(C(=O)O)(F)F.NC1=NC(=NS1)C(C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)CCl)C(=O)O)C1=O)=NOC.CN1CCN(CC1)C(=O)OC(C)(C)C>>NC1=NC(=NS1)C(C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C[N+]2(CCNCC2)C)C(=O)[O-])C1=O)=NOC | CC(C)(C)OC(=O)[N:22]1[CH2:21][CH2:20][N:18]([CH3:19])[CH2:24][CH2:23]1.Cl[CH2:17][C:16]1=[C:12]([C:13](=[O:14])[OH:15])[N:11]2[C:9](=[O:10])[C@@H:8]([NH:7][C:5]([C:4](=[N:3][O:2][CH3:1])[c:28]3[n:29][s:30][c:31]([NH2:32])[n:33]3)=[O:6])[C@H:27]2[S:26][CH2:25]1>>[CH3:1][O:2][N:3]=[C:4]([C:5](=[O:6])[NH:7][C@@H:8]1[C:9](... | CN1CCN(C(=O)OC(C)(C)C)CC1.CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(CCl)CS[C@H]12)c1nsc(N)n1 | CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCNCC3)CS[C@H]12)c1nsc(N)n1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 37ec5efd319715498aa716286cb5dbe164886d3b85a5337c2ffefe62bda054e7 | 01357b708f58664aeab786c7735bff696889ae4504065f45cfe2fc04b7ed3069 | N=C(C(=O)N[C@@H]1C(=O)N2C=C(C[NH+]3CCNCC3)CS[C@H]12)c1ncsn1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[N;H0;D3;+0:4](-[C;D1;H3:5])-[C:6]-[C:7]-1.Cl-[CH2;D2;+0:8]-[C:9](=[C:10](-[C:11](=[O;D1;H0:12])-[OH;D1;+0:13])-[#7:14]-[C:15]=[O;D1;H0:16])-[C:17]-[#16:18]>>[#16:18]-[C:17]-[C:9](-[CH2;D2;+0:8]-[N+;H0;D4:4]1(-[C;D1;H3:5])-[C:3]-[C:2]-[NH;D2;+0:1]-[C:7]-[C:6]-1)=[C:10](-[... | null | [] | null | null | 30 | MINUTE | To a solution of 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylic acid trifluoroacetate (syn isomer) in N,N-dimethylformamide (150 ml) was added 1-methyl-4-tert-butoxycarbonylpiperazine (30 g). After being stirred at room temperature for 30 minutes, the mixture was add... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester.Carboxylic acid.Ether.Tertiary amine.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH+]CCN1 | C1=CN2CC[C@H]2SC1.C1C[NH+]CCN1.c1ncsn1 | HCl | CN(C=O)C | null | 0.5 | CN1CCN(C(=O)OC(C)(C)C)CC1.CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(CCl)CS[C@H]12)c1nsc(N)n1>CN(C=O)C>CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCNCC3)CS[C@H]12)c1nsc(N)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-fb89a90e5efb421fbb23e563617fd178 | CC(C)(C)OC(=O)CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCN(C(=O)OC(C)(C)C)CC3)CS[C@H]12)c1csc(NC=O)n1>>C[N+]1(CC2=C(C(=O)[O-])N3C(=O)[C@@H](NC(=O)C(=NOCC(=O)O)c4csc(N)n4)[C@H]3SC2)CCNCC1 | Cl.C(=O)NC=1SC=C(N1)C(C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C[N+]2(CCN(CC2)C(=O)OC(C)(C)C)C)C(=O)[O-])C1=O)=NOCC(=O)OC(C)(C)C.Cl.C(C)(=O)OCC>>NC=1SC=C(N1)C(C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C[N+]2(CCNCC2)C)C(=O)[O-])C1=O)=NOCC(=O)O | CC(C)(C)OC(=O)[N:34]1[CH2:33][CH2:32][N+:2]([CH3:1])([CH2:3][C:4]2=[C:5]([C:6](=[O:7])[O-:8])[N:9]3[C:10](=[O:11])[C@@H:12]([NH:13][C:14](=[O:15])[C:16](=[N:17][O:18][CH2:19][C:20](=[O:21])[O:22]C(C)(C)C)[c:23]4[cH:24][s:25][c:26]([NH:27]C=O)[n:28]4)[C@H:29]3[S:30][CH2:31]2)[CH2:36][CH2:35]1>>[CH3:1][N+:2]1([CH2:3][C:4... | CC(C)(C)OC(=O)CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCN(C(=O)OC(C)(C)C)CC3)CS[C@H]12)c1csc(NC=O)n1 | C[N+]1(CC2=C(C(=O)[O-])N3C(=O)[C@@H](NC(=O)C(=NOCC(=O)O)c4csc(N)n4)[C@H]3SC2)CCNCC1 | null | null | CO | Reduction | OtherReaction | bf9f37cb6352d975706fe0f05561dfa28add5a55ca2b6e731ff11a924eae65d8 | 0f151cf844bf1bb06ac48600a770444e4c8cc62144896aac3c26c07a465f07d0 | N=C(C(=O)N[C@@H]1C(=O)N2C=C(C[NH+]3CCNCC3)CS[C@H]12)c1cscn1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7;+:4]-[C:5]-[C:6]-1.C-C(-C)(-C)-[O;H0;D2;+0:7]-[C:8](-[C:9])=[O;D1;H0:10].O=C-[NH;D2;+0:11]-[c:12]1:[#16;a:13]:[c:14]:[c:15]:[#7;a:16]:1>>[#7;+:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1.[C:9]-[C:8](=[O;D1;H0:10])-[OH;D1;+0:7].[NH2;D1;+0:11]-[c:12]1:[#16;a:13]:[c:14]:[... | 26.7 | [{"value": 26.7, "product": "NC=1SC=C(N1)C(C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C[N+]2(CCNCC2)C)C(=O)[O-])C1=O)=NOCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4.5 | HOUR | To a suspension of 7β-[2-(2-formamidothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-(1-methyl-4-tert-butoxycarbonyl-1-piperazinio)methyl-3-cephem-4-carboxylate hydrochloride (syn isomer) (4.02 g) in methanol (12 ml) was added conc. hydrochloric acid (4.4 ml) at 10° C. The resulting solution was warmed to r... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Secondary amide.Boc.Boc | Carboxylic acid.Primary amine.Secondary amine | C1C[NH+]CC[NH]1 | C1C[NH+]CCN1 | C1=CN2CC[C@H]2SC1.c1cscn1.C1C[NH+]CCN1 | HO- | CO | null | 4.5 | CC(C)(C)OC(=O)CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCN(C(=O)OC(C)(C)C)CC3)CS[C@H]12)c1csc(NC=O)n1>CO>C[N+]1(CC2=C(C(=O)[O-])N3C(=O)[C@@H](NC(=O)C(=NOCC(=O)O)c4csc(N)n4)[C@H]3SC2)CCNCC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-55ffa67baea94d4f88c43cf174843b6b | CN1CCN(C(=O)c2ccc(O)c(O)c2)CC1.CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(CCl)CS[C@H]12)c1csc(NC=O)n1>>CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCN(C(=O)c4ccc(O)c(O)c4)CC3)CS[C@H]12)c1csc(NC=O)n1 | C(C)(=O)OCC.C(=O)NC=1SC=C(N1)C(C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)CCl)C(=O)O)C1=O)=NOC.CN1CCN(CC1)C(C1=CC(=C(C=C1)O)O)=O>>C(=O)NC=1SC=C(N1)C(C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C[N+]2(CCN(CC2)C(C2=CC(=C(C=C2)O)O)=O)C)C(=O)[O-])C1=O)=NOC | [N:18]1([CH3:19])[CH2:20][CH2:21][N:22]([C:23](=[O:24])[c:25]2[cH:26][cH:27][c:28]([OH:29])[c:30]([OH:31])[cH:32]2)[CH2:33][CH2:34]1.Cl[CH2:17][C:16]1=[C:12]([C:13](=[O:14])[OH:15])[N:11]2[C:9](=[O:10])[C@@H:8]([NH:7][C:5]([C:4](=[N:3][O:2][CH3:1])[c:38]3[cH:39][s:40][c:41]([NH:42][CH:43]=[O:44])[n:45]3)=[O:6])[C@H:37]... | CN1CCN(C(=O)c2ccc(O)c(O)c2)CC1.CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(CCl)CS[C@H]12)c1csc(NC=O)n1 | CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCN(C(=O)c4ccc(O)c(O)c4)CC3)CS[C@H]12)c1csc(NC=O)n1 | null | null | CN(C=O)C | Functional Group Interconversion | OtherReaction | 511bf7d10783e9de01f4ae658b25b30801ba121b9d0efc2589106127c89aaa03 | c8557186a9769d56d4131cf98797065b79da099d927f5093fc211d3e2ca1f543 | N=C(C(=O)N[C@@H]1C(=O)N2C=C(C[NH+]3CCN(C(=O)c4ccccc4)CC3)CS[C@H]12)c1cscn1 | Cl-[CH2;D2;+0:1]-[C:2](=[C:3](-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6])-[#7:7]-[C:8]=[O;D1;H0:9])-[C:10]-[#16:11].[C;D1;H3:12]-[N;H0;D3;+0:13]1-[C:14]-[C:15]-[#7:16]-[C:17]-[C:18]-1>>[#16:11]-[C:10]-[C:2](-[CH2;D2;+0:1]-[N+;H0;D4:13]1(-[C;D1;H3:12])-[C:14]-[C:15]-[#7:16]-[C:17]-[C:18]-1)=[C:3](-[C:4](-[O-;H0;D1:6])=[O;D1;H0:5... | 115.9 | [{"value": 115.9, "product": "C(=O)NC=1SC=C(N1)C(C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C[N+]2(CCN(CC2)C(C2=CC(=C(C=C2)O)O)=O)C)C(=O)[O-])C1=O)=NOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 3.5 | HOUR | To a solution of 7β-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylic acid (syn isomer) (920 mg) in N,N-dimethylformamide (5 ml) was added 1-methyl-4-(3,4-dihydroxybenzoyl)piperazine (945 mg) at 0° C. and the mixture was stirred at 0° C. for 3.5 hours. The mixture was added drop... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid.Tertiary amine | null | C1C[NH]CC[NH]1 | C1C[NH+]CC[NH]1 | C1=CN2CC[C@H]2SC1.C1C[NH+]CC[NH]1.c1ccccc1.c1cscn1 | HCl | CN(C=O)C | 0 | 3.5 | CN1CCN(C(=O)c2ccc(O)c(O)c2)CC1.CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(CCl)CS[C@H]12)c1csc(NC=O)n1>CN(C=O)C>CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCN(C(=O)c4ccc(O)c(O)c4)CC3)CS[C@H]12)c1csc(NC=O)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1f2f42fc73044a5984d82eb3c72b03d5 | C=CCON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(CCl)CS[C@H]12)c1nsc(N)n1.CN1CCN(C(=O)c2cc(O)c(O)cn2)CC1>>C=CCON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCN(C(=O)c4cc(O)c(O)cn4)CC3)CS[C@H]12)c1nsc(N)n1 | C(C)(=O)OCC.C(C)C(C(=O)[O-])CCCC.[Na+].CN1CCN(CC1)C(=O)C1=NC=C(C(=C1)O)O.FC(C(=O)O)(F)F.NC1=NC(=NS1)C(C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)CCl)C(=O)O)C1=O)=NOCC=C>>NC1=NC(=NS1)C(C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C[N+]2(CCN(CC2)C(=O)C2=NC=C(C(=C2)O)O)C)C(=O)[O-])C1=O)=NOCC=C | Cl[CH2:19][C:18]1=[C:14]([C:15](=[O:16])[OH:17])[N:13]2[C:11](=[O:12])[C@@H:10]([NH:9][C:7]([C:6](=[N:5][O:4][CH2:3][CH:2]=[CH2:1])[c:40]3[n:41][s:42][c:43]([NH2:44])[n:45]3)=[O:8])[C@H:39]2[S:38][CH2:37]1.[N:20]1([CH3:21])[CH2:22][CH2:23][N:24]([C:25](=[O:26])[c:27]2[cH:28][c:29]([OH:30])[c:31]([OH:32])[cH:33][n:34]2)... | C=CCON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(CCl)CS[C@H]12)c1nsc(N)n1.CN1CCN(C(=O)c2cc(O)c(O)cn2)CC1 | C=CCON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCN(C(=O)c4cc(O)c(O)cn4)CC3)CS[C@H]12)c1nsc(N)n1 | null | null | CS(=O)C | Functional Group Interconversion | OtherReaction | 511bf7d10783e9de01f4ae658b25b30801ba121b9d0efc2589106127c89aaa03 | c8557186a9769d56d4131cf98797065b79da099d927f5093fc211d3e2ca1f543 | N=C(C(=O)N[C@@H]1C(=O)N2C=C(C[NH+]3CCN(C(=O)c4ccccn4)CC3)CS[C@H]12)c1ncsn1 | Cl-[CH2;D2;+0:1]-[C:2](=[C:3](-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6])-[#7:7]-[C:8]=[O;D1;H0:9])-[C:10]-[#16:11].[C;D1;H3:12]-[N;H0;D3;+0:13]1-[C:14]-[C:15]-[#7:16]-[C:17]-[C:18]-1>>[#16:11]-[C:10]-[C:2](-[CH2;D2;+0:1]-[N+;H0;D4:13]1(-[C;D1;H3:12])-[C:14]-[C:15]-[#7:16]-[C:17]-[C:18]-1)=[C:3](-[C:4](-[O-;H0;D1:6])=[O;D1;H0:5... | 34.2 | [{"value": 34.2, "product": "NC1=NC(=NS1)C(C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C[N+]2(CCN(CC2)C(=O)C2=NC=C(C(=C2)O)O)C)C(=O)[O-])C1=O)=NOCC=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a suspension of 1-methyl-4-(4,5-dihydroxy-2-pyridylcarbonyl)piperazine (800 mg) in dimethyl sulfoxide (8 ml) was added sodium 2-ethylhexanoate (840 mg). The solution was added dropwise a solution of 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-allyloxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate trifluoroacetate... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid.Tertiary amine | null | C1C[NH]CC[NH]1 | C1C[NH+]CC[NH]1 | C1=CN2CC[C@H]2SC1.C1C[NH+]CC[NH]1.c1ccncc1.c1ncsn1 | HCl | CS(=O)C | null | 4 | C=CCON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(CCl)CS[C@H]12)c1nsc(N)n1.CN1CCN(C(=O)c2cc(O)c(O)cn2)CC1>CS(=O)C>C=CCON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCN(C(=O)c4cc(O)c(O)cn4)CC3)CS[C@H]12)c1nsc(N)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-badf125e1b9643a4b3de78dd9442d0c1 | CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCN(C(=O)c4ccc(O)c(O)c4)CC3)CS[C@H]12)c1csc(NC=O)n1>>CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCN(C(=O)c4ccc(O)c(O)c4)CC3)CS[C@H]12)c1csc(N)n1 | C([O-])(O)=O.[Na+].Cl.C(=O)NC=1SC=C(N1)C(C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C[N+]2(CCN(CC2)C(C2=CC(=C(C=C2)O)O)=O)C)C(=O)[O-])C1=O)=NOC>>NC=1SC=C(N1)C(C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C[N+]2(CCN(CC2)C(C2=CC(=C(C=C2)O)O)=O)C)C(=O)[O-])C1=O)=NOC | O=C[NH:42][c:41]1[s:40][cH:39][c:38]([C:4](=[N:3][O:2][CH3:1])[C:5](=[O:6])[NH:7][C@@H:8]2[C:9](=[O:10])[N:11]3[C:12]([C:13](=[O:14])[O-:15])=[C:16]([CH2:17][N+:18]4([CH3:19])[CH2:20][CH2:21][N:22]([C:23](=[O:24])[c:25]5[cH:26][cH:27][c:28]([OH:29])[c:30]([OH:31])[cH:32]5)[CH2:33][CH2:34]4)[CH2:35][S:36][C@H:37]23)[n:4... | CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCN(C(=O)c4ccc(O)c(O)c4)CC3)CS[C@H]12)c1csc(NC=O)n1 | CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCN(C(=O)c4ccc(O)c(O)c4)CC3)CS[C@H]12)c1csc(N)n1 | null | null | CO | Reduction | Reduction of primary amides to amines | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | N=C(C(=O)N[C@@H]1C(=O)N2C=C(C[NH+]3CCN(C(=O)c4ccccc4)CC3)CS[C@H]12)c1cscn1 | O=C-[NH;D2;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[c:5]:[#7;a:6]:1>>[NH2;D1;+0:1]-[c:2]1:[#16;a:3]:[c:4]:[c:5]:[#7;a:6]:1 | 37.7 | [{"value": 37.7, "product": "NC=1SC=C(N1)C(C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C[N+]2(CCN(CC2)C(C2=CC(=C(C=C2)O)O)=O)C)C(=O)[O-])C1=O)=NOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a suspension of 7β-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-[1-methyl-4-(3,4-dihydroxybenzoyl)-1-piperazinio]methyl-3-cephem-4-carboxylate (syn isomer) (1.52 g) in methanol (9 ml) was added concentrated hydrochloric acid (1.92 ml). After being stirred at room temperature for 4 hours, the solution was ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | C1=CN2CC[C@H]2SC1.C1C[NH+]CC[NH]1.c1ccccc1.c1cscn1 | Other | CO | null | 4 | CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCN(C(=O)c4ccc(O)c(O)c4)CC3)CS[C@H]12)c1csc(NC=O)n1>CO>CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCN(C(=O)c4ccc(O)c(O)c4)CC3)CS[C@H]12)c1csc(N)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d576ec8dc5e942d7a4fd333adedd0dc3 | CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCNCC3)CS[C@H]12)c1nsc(N)n1.O=C(O)c1cc(O)c(O)cn1>>CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCN(C(=O)c4cc(O)c(O)cn4)CC3)CS[C@H]12)c1nsc(N)n1 | C(C)(C)OC(C)C.NC1=NC(=NS1)C(C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C[N+]2(CCNCC2)C)C(=O)[O-])C1=O)=NOC.C[Si](NC(C)=O)(C)C.OC1=CC(=NC=C1O)C(=O)O.ON1N=NC2=C1C=CC=C2.C1(CCCCC1)N=C=NC1CCCCC1>>NC1=NC(=NS1)C(C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C[N+]2(CCN(CC2)C(=O)C2=NC=C(C(=C2)O)O)C)C(=O)[O-])C1=O)=NOC | [CH3:1][O:2][N:3]=[C:4]([C:5](=[O:6])[NH:7][C@@H:8]1[C:9](=[O:10])[N:11]2[C:12]([C:13](=[O:14])[O-:15])=[C:16]([CH2:17][N+:18]3([CH3:19])[CH2:20][CH2:21][NH:22][CH2:33][CH2:34]3)[CH2:35][S:36][C@H:37]12)[c:38]1[n:39][s:40][c:41]([NH2:42])[n:43]1.O[C:23](=[O:24])[c:25]1[cH:26][c:27]([OH:28])[c:29]([OH:30])[cH:31][n:32]1... | CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCNCC3)CS[C@H]12)c1nsc(N)n1.O=C(O)c1cc(O)c(O)cn1 | CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCN(C(=O)c4cc(O)c(O)cn4)CC3)CS[C@H]12)c1nsc(N)n1 | null | null | CS(=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | e47d96c9361a012293d76c3f121f4ccd40981f3fc68d72319df036f78dd5f08e | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | N=C(C(=O)N[C@@H]1C(=O)N2C=C(C[NH+]3CCN(C(=O)c4ccccn4)CC3)CS[C@H]12)c1ncsn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[#7;+:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7;+:7]-[C:12]-[C:11]-1)-[c:3](:[c:4]):[#7;a:5]:[c:6] | 3.9 | [{"value": 3.9, "product": "NC1=NC(=NS1)C(C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C[N+]2(CCN(CC2)C(=O)C2=NC=C(C(=C2)O)O)C)C(=O)[O-])C1=O)=NOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 4,5-dihydroxy-2-pyridinecarboxylic acid (3.1 g) and 1-hydroxybenzotriazole (4.0 g) in dimethyl sulfoxide (30 ml) was added N,N'-dicyclohexylcarbodiimide (6.2 g). After being stirred at room temperature for 1 hour, the reaction mixture was added to a solution of 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-m... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1C[NH+]CCN1 | C1C[NH+]CC[NH]1 | C1=CN2CC[C@H]2SC1.C1C[NH+]CC[NH]1.c1ccncc1.c1ncsn1 | HO- | CS(=O)C | null | 1 | CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCNCC3)CS[C@H]12)c1nsc(N)n1.O=C(O)c1cc(O)c(O)cn1>CS(=O)C>CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCN(C(=O)c4cc(O)c(O)cn4)CC3)CS[C@H]12)c1nsc(N)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b271669b85e646cfaf401d72445f4700 | CC(=O)Oc1cnc(C(=O)Cl)cc1OC(C)=O.CCON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCNCC3)CS[C@H]12)c1nsc(N)n1>>CCON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCN(C(=O)c4cc(O)c(O)cn4)CC3)CS[C@H]12)c1nsc(N)n1 | NC1=NC(=NS1)C(C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C[N+]2(CCNCC2)C)C(=O)[O-])C1=O)=NOCC.Cl.C(C)(=O)OC1=CC(=NC=C1OC(C)=O)C(=O)Cl.C([O-])(O)=O.[Na+]>>NC1=NC(=NS1)C(C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C[N+]2(CCN(CC2)C(=O)C2=NC=C(C(=C2)O)O)C)C(=O)[O-])C1=O)=NOCC | CC(=O)[O:29][c:28]1[cH:27][c:26]([C:24](Cl)=[O:25])[n:33][cH:32][c:30]1[O:31]C(C)=O.[CH3:1][CH2:2][O:3][N:4]=[C:5]([C:6](=[O:7])[NH:8][C@@H:9]1[C:10](=[O:11])[N:12]2[C:13]([C:14](=[O:15])[O-:16])=[C:17]([CH2:18][N+:19]3([CH3:20])[CH2:21][CH2:22][NH:23][CH2:34][CH2:35]3)[CH2:36][S:37][C@H:38]12)[c:39]1[n:40][s:41][c:42]... | CC(=O)Oc1cnc(C(=O)Cl)cc1OC(C)=O.CCON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCNCC3)CS[C@H]12)c1nsc(N)n1 | CCON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCN(C(=O)c4cc(O)c(O)cn4)CC3)CS[C@H]12)c1nsc(N)n1 | null | null | O.CC(=O)C | Acylation | OtherReaction | cf01b5df9088496bd10db3298095e41d9d3cab861a1a6451d13c45e1f1ab45db | 5214b83f6e2bb1b62d2ef28640d266abbdeda6fd4959fafbaca87c3fd32f11d7 | N=C(C(=O)N[C@@H]1C(=O)N2C=C(C[NH+]3CCN(C(=O)c4ccccn4)CC3)CS[C@H]12)c1ncsn1 | C-C(=O)-[O;H0;D2;+0:1]-[c:2]1:[c:3]:[c:4](-[C;H0;D3;+0:5](-Cl)=[O;D1;H0:6]):[#7;a:7]:[c:8]:[c:9]:1-[O;H0;D2;+0:10]-C(-C)=O.[#7;+:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[O;D1;H0:6]=[C;H0;D3;+0:5](-[N;H0;D3;+0:14]1-[C:13]-[C:12]-[#7;+:11]-[C:16]-[C:15]-1)-[c:4]1:[#7;a:7]:[c:8]:[c:9](-[OH;D1;+0:10]):[c:2](-[OH;... | 47.9 | [{"value": 47.9, "product": "NC1=NC(=NS1)C(C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C[N+]2(CCN(CC2)C(=O)C2=NC=C(C(=C2)O)O)C)C(=O)[O-])C1=O)=NOCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido]-3-(1-methyl-1-piperazinio)methyl-3-cephem-4-carboxylate (syn isomer) (255 mg) in a mixture of water (5 ml) and acetone (5 ml) was added 4,5-diacetoxy-2-pyridinecarbonyl chloride hydrochloride (309 mg), with maintaining the pH of the solution... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester.Ester.Secondary amine | Tertiary amide.Aromatic alcohol.Aromatic alcohol | C1C[NH+]CCN1 | C1C[NH+]CC[NH]1 | C1=CN2CC[C@H]2SC1.C1C[NH+]CC[NH]1.c1ccncc1.c1ncsn1 | HCl | O.CC(=O)C | null | 0.5 | CC(=O)Oc1cnc(C(=O)Cl)cc1OC(C)=O.CCON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCNCC3)CS[C@H]12)c1nsc(N)n1>O.CC(=O)C>CCON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCN(C(=O)c4cc(O)c(O)cn4)CC3)CS[C@H]12)c1nsc(N)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-470255b2b67b486898084bd101cb65db | Cl>>Cl | Cl.NC1=NC(=NS1)C(C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C[N+](CC=2NC=C(C(C2)=O)O)(C)C)C(=O)[O-])C1=O)=NOC(C)(C)C(=O)O>>Cl.NC1=NC(=NS1)C(C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C[N+](CC=2NC=C(C(C2)=O)O)(C)C)C(=O)[O-])C1=O)=NOC(C)(C)C(=O)O | [ClH:44]>>[ClH:44] | Cl | Cl | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | To 1N hydrochloric acid was added 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-[N,N-dimethyl-N-((5-hydroxy-4-oxo-1,4-dihydropyridin-2-yl)methyl}ammonio]methyl-3-cephem-4-carboxylate (syn isomer) (2.2 g). The mixture was stirred under ice-cooling for 3 hours. The resulting precipit... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | null | null | null | Cl>>Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-fc2653c706e943b8b80ddf6fb2c55f7f | O=[N+]([O-])c1ccc(Cl)cc1.Sc1nsc(S)n1.[OH-]>>O=[N+]([O-])c1ccc(Sc2nsc(Sc3ccc([N+](=O)[O-])cc3)n2)cc1 | ClC1=CC=C(C=C1)[N+](=O)[O-].[OH-].[Na+].SC1=NSC(=N1)S>>[N+](=O)([O-])C1=CC=C(C=C1)SC1=NSC(=N1)SC1=CC=C(C=C1)[N+](=O)[O-] | Cl[c:7]1[cH:6][cH:5][c:17]([N+:18](=[O:19])[O-:20])[cH:4][cH:24]1.[n:2]1[c:9]([SH:8])[n:10][s:11][c:12]1[SH:13].[OH-:1]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([S:8][c:9]2[n:10][s:11][c:12]([S:13][c:14]3[cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21][cH:22]3)[n:23]2)[cH:24][cH:25]1 | O=[N+]([O-])c1ccc(Cl)cc1.Sc1nsc(S)n1.[OH-] | O=[N+]([O-])c1ccc(Sc2nsc(Sc3ccc([N+](=O)[O-])cc3)n2)cc1 | null | null | CN(C)C=O.O | Aromatic Heterocycle Formation | OtherReaction | d6d1f72775c5d476329e874d98c360578641590005804cc329a91ba10ffc2b66 | 9ce8cecd24ca72e38fa1e8ac5a04feb7aa7ca915023db7e29a89863779f9a99d | c1ccc(Sc2nsc(Sc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[c;H0;D3;+0:4](-[#7;+:5](-[O;-;D1;H0:6])=[O;D1;H0:7]):[cH;D2;+0:8]:[cH;D2;+0:9]:1.[OH-;D0:10].[SH;D1;+0:11]-[c;H0;D3;+0:12]1:[#16;a:13]:[#7;a:14]:[c;H0;D3;+0:15](-[SH;D1;+0:16]):[n;H0;D2;+0:17]:1>>[O;-;D1;H0:6]-[#7;+:5](=[O;D1;H0:7])-[c;H0;D3;+0:4]1:[c:18]:[c:19]:[c:20](-[S;H0;D2;+... | 92 | [{"value": 92.0, "product": "[N+](=O)([O-])C1=CC=C(C=C1)SC1=NSC(=N1)SC1=CC=C(C=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.7, "product": "[N+](=O)([O-])C1=CC=C(C=C1)SC1=NSC(=N1)SC1=CC=C(C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | 3 g of NaOH were dissolved in 5 ml of water in a 250 ml three-necked flask, 3.8 g (25 mmol) of 3,5-dimer-capto-1,2,4-thiadiazole (preparation analogous to U.S. No. 3,899,502 or Z. Anorgan. Allgem. Chemie volume 486 (1982), pages 111-115) were added and the mixture was heated to 100° C. 79 g (50 mmol) of 1-chloro-4-nitr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Nitro group.Aromatic thiol.Aromatic thiol | Nitro group.Nitro group.Monosulfide.Monosulfide | c1ccccc1.c1ncsn1 | c1ccccc1.c1ncsn1.c1ccccc1 | c1ccccc1.c1ncsn1.c1ccccc1 | null | CN(C)C=O.O | 100 | null | O=[N+]([O-])c1ccc(Cl)cc1.Sc1nsc(S)n1.[OH-]>CN(C)C=O.O>O=[N+]([O-])c1ccc(Sc2nsc(Sc3ccc([N+](=O)[O-])cc3)n2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0d6c5b16d69b4534bf86c0fb3c59c329 | BrCCCCBr.O=S(=O)(O)O.Oc1cccc(O)c1.[OH-]>>Oc1cccc(OCCCCOc2cccc(O)c2)c1 | [OH-].[K+].C1(O)=CC(O)=CC=C1.S(O)(O)(=O)=O.BrCCCCBr>>OC=1C=C(OCCCCOC2=CC(=CC=C2)O)C=CC1 | Br[CH2:8][CH2:9][CH2:2][CH2:20]Br.O=S(=O)(O)[OH:7].[OH:12][c:13]1[cH:14][cH:15][cH:16][c:17]([OH:18])[cH:19]1.[OH-:1]>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][c:13]2[cH:14][cH:15][cH:16][c:17]([OH:18])[cH:19]2)[cH:20]1 | BrCCCCBr.O=S(=O)(O)O.Oc1cccc(O)c1.[OH-] | Oc1cccc(OCCCCOc2cccc(O)c2)c1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | e6ffb2faee7dd6e7b0626caef33854c44061fa0c4984b3a90eb791d165d728d5 | fdaa1813c7944a55b8970d6214b8c93d9eab4178705d897cc8ff86d898cadbe3 | c1ccc(OCCCCOc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-Br.O-S(=O)(=O)-[OH;D1;+0:5].[OH-;D0:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[OH;D1;+0:6]-[c;H0;D3;+0:2]1:[c:11]:[c:12]:[c:13]:[c:14](-[O;H0;D2;+0:5]-[CH2;D2;+0:4]-[CH2;D2;+0:3]-[C:15]-[C:16]-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]):[cH;D2;+0:1]:1 | null | [] | null | null | 8 | HOUR | A five neck five liter round bottom flask equipped with a mechanical stirrer, two condensers, and a dropping funnel is purged with nitrogen then charged under a nitrogen blanket with 1.5 kg (13.6 moles) resorcinol, 120 grams deionized water, and 138.75 grams (0.64 moles) 1,4-dibromobutane. The reaction slurry is slowly... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Aromatic alcohol | Ether.Ether.Aromatic alcohol | null | c1ccccc1 | c1ccccc1.c1ccccc1 | null | O | null | 8 | BrCCCCBr.O=S(=O)(O)O.Oc1cccc(O)c1.[OH-]>O>Oc1cccc(OCCCCOc2cccc(O)c2)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-04e07f48769d45fb9b3405fdf6365184 | BrCCCCBr.Oc1ccc(O)cc1.[OH-].[OH-]>>Oc1ccc(OCCCCOc2ccc(O)cc2)cc1 | [OH-].[K+].C1(O)=CC=C(O)C=C1.BrCCCCBr.[OH-].[K+].[OH-].[K+]>>OC1=CC=C(OCCCCOC2=CC=C(C=C2)O)C=C1 | Br[CH2:4][CH2:3][CH2:8][CH2:5]Br.[OH:1][c:2]1[cH:13][cH:14][c:15]([OH:16])[cH:17][cH:20]1.[OH-:11].[OH-:6]>>[OH:1][c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]2[cH:13][cH:14][c:15]([OH:16])[cH:17][cH:18]2)[cH:19][cH:20]1 | BrCCCCBr.Oc1ccc(O)cc1.[OH-].[OH-] | Oc1ccc(OCCCCOc2ccc(O)cc2)cc1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | a433113afb572656691553e0b9980eaa9212a47e371735e50c7ed3fa0d356e8f | fdaa1813c7944a55b8970d6214b8c93d9eab4178705d897cc8ff86d898cadbe3 | c1ccc(OCCCCOc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-Br.[O;D1;H1:5]-[c:6]1:[c:7]:[cH;D2;+0:8]:[c;H0;D3;+0:9](-[O;D1;H1:10]):[cH;D2;+0:11]:[cH;D2;+0:12]:1.[OH-;D0:13].[OH-;D0:14]>>[O;D1;H1:5]-[c:6]1:[c:7]:[cH;D2;+0:8]:[c:15](-[O;H0;D2;+0:13]-[C:16]-[C:17]-[CH2;D2;+0:3]-[C:18]-[O;H0;D2;+0:14]-[c;H0;D3;+0:4]2:[c:19]... | 46 | [{"value": 46.0, "product": "OC1=CC=C(OCCCCOC2=CC=C(C=C2)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A five neck five liter round bottom flask equipped with a mechanical stirrer, two condensers, and a dropping funnel is purged with nitrogen then charged under a nitrogen blanket with 1.25 kg (11.36 moles) hydroquinone, 350 grams deionized water, and 231.25 grams (1.07 moles) 1,4-dibromobutane. The reaction mass becomes... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Aromatic alcohol | Ether.Ether.Aromatic alcohol | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | Br- | O | null | 8 | BrCCCCBr.Oc1ccc(O)cc1.[OH-].[OH-]>O>Oc1ccc(OCCCCOc2ccc(O)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b21f5d35f68c4e3ead3485ab0ba70fbb | BrCCCCCCCCBr.Oc1ccc(O)cc1.[OH-].[OH-]>>Oc1ccc(OCCCCCCCCOc2ccc(O)cc2)cc1 | C1(O)=CC=C(O)C=C1.[OH-].[K+].[OH-].[K+].[OH-].[K+].BrCCCCCCCCBr>>OC1=CC=C(OCCCCCCCCOC2=CC=C(C=C2)O)C=C1 | Br[CH2:5][CH2:23][CH2:24][CH2:7][CH2:11][CH2:12][CH2:13][CH2:14]Br.[OH:1][c:2]1[cH:3][cH:4][c:19]([OH:20])[cH:21][cH:22]1.[OH-:6].[OH-:15]>>[OH:1][c:2]1[cH:3][cH:4][c:5]([O: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]([OH:20])[cH:21][cH:22]2)[cH:23][cH:24]1 | BrCCCCCCCCBr.Oc1ccc(O)cc1.[OH-].[OH-] | Oc1ccc(OCCCCCCCCOc2ccc(O)cc2)cc1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | fe468b15bad24fc50ee155d266d9162241ea7aa8d8d56f38a6e9639e490d1b62 | 08134ccf30e746cd0aac5a54b51fcfee17628d21c85642ad552f88fc52be57f9 | c1ccc(OCCCCCCCCOc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-Br.[O;D1;H1:9]-[c;H0;D3;+0:10]1:[c:11]:[cH;D2;+0:12]:[c;H0;D3;+0:13](-[O;D1;H1:14]):[c:15]:[cH;D2;+0:16]:1.[OH-;D0:17].[OH-;D0:18]>>[O;D1;H1:9]-[c;H0;D3;+0:10]1:[c:11]:[cH;D2;+0:12]:[c;H0;D3;+0:8](-[O;H0;D2;+0:17]-[CH2;D2... | 99 | [{"value": 99.0, "product": "OC1=CC=C(OCCCCCCCCOC2=CC=C(C=C2)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 90 | MINUTE | A five neck five liter round bottom flask equipped with a mechanical stirrer, two condensers, and a dropping funnel is purged with nitrogen then charged under a nitrogen blanket with 1.1 kg (10.0 moles) hydroquinone, 350 grams deionized water, and 272.0 grams (1.0 moles) 1,8-dibromooctane. The reaction mass becomes a s... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Aromatic alcohol.Aromatic alcohol | Ether.Ether.Aromatic alcohol.Aromatic alcohol | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | Br- | O | null | 1.5 | BrCCCCCCCCBr.Oc1ccc(O)cc1.[OH-].[OH-]>O>Oc1ccc(OCCCCCCCCOc2ccc(O)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d7ebeb5510864bf5a76d01a064162923 | BrCCCCCCCCBr.Oc1cccc(O)c1.[OH-].[OH-]>>Oc1cccc(OCCCCCCCCOc2cccc(O)c2)c1 | C1(O)=CC(O)=CC=C1.[OH-].[K+].[OH-].[K+].[OH-].[K+].BrCCCCCCCCBr>>OC=1C=C(OCCCCCCCCOC2=CC(=CC=C2)O)C=CC1 | Br[CH2:2][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]Br.[OH:16][c:17]1[cH:18][cH:19][cH:20][c:21]([OH:22])[cH:23]1.[OH-:1].[OH-:7]>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][c:17]2[cH:18][cH:19][cH:20][c:21]([OH:22])[cH:23]2)[cH:24]1 | BrCCCCCCCCBr.Oc1cccc(O)c1.[OH-].[OH-] | Oc1cccc(OCCCCCCCCOc2cccc(O)c2)c1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | e6ffb2faee7dd6e7b0626caef33854c44061fa0c4984b3a90eb791d165d728d5 | fdaa1813c7944a55b8970d6214b8c93d9eab4178705d897cc8ff86d898cadbe3 | c1ccc(OCCCCCCCCOc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].Br-[CH2;D2;+0:5]-[C:6]-[C:7].[OH-;D0:8].[OH-;D0:9].[OH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:4]-[C:3]-[CH2;D2;+0:2]-[C:14]-[O;H0;D2;+0:9]-[c:15]1:[c:16]:[c;H0;D3;+0:1](-[OH;D1;+0:8]):[c:17]:[c:18]:[c:19]:1.[C:7]-[C:6]-[CH2;D2;+0:5]-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13] | 27 | [{"value": 27.0, "product": "OC=1C=C(OCCCCCCCCOC2=CC(=CC=C2)O)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 10 | CELSIUS | null | null | A five neck five liter round bottom flask equipped with a mechanical stirrer, two condensers, and a dropping funnel is purged with nitrogen then charged under a nitrogen blanket with 1.6 kg (14.5 moles) resorcinol, 160 grams deionized water, and 296.7 grams (1.091 moles) 1,8-dibromooctane. The easily stirable reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Aromatic alcohol | Ether.Ether.Aromatic alcohol | null | c1ccccc1 | c1ccccc1.c1ccccc1 | Br- | O | 10 | null | BrCCCCCCCCBr.Oc1cccc(O)c1.[OH-].[OH-]>O>Oc1cccc(OCCCCCCCCOc2cccc(O)c2)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6a57ab6cf73c4e56abcc682a99f57c0a | CCCCCCCCCCCCC1(Cc2cc(O)ccc2O)COCCOCC(C)(C)COCCOC1>>CCCCCCCCCCCCC1(CC2=CC(=O)C=CC2=O)COCCOCC(C)(C)COCCOC1 | C(CCCCCCCCCCC)C1(COCCOCC(COCCOC1)(C)C)CC1=C(C=CC(=C1)O)O>>C(CCCCCCCCCCC)C1(COCCOCC(COCCOC1)(C)C)CC1=CC(C=CC1=O)=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][C:13]1([CH2:14][c:15]2[cH:16][c:17]([OH:18])[cH:19][cH:20][c:21]2[OH:22])[CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][C:29]([CH3:30])([CH3:31])[CH2:32][O:33][CH2:34][CH2:35][O:36][CH2:37]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]... | CCCCCCCCCCCCC1(Cc2cc(O)ccc2O)COCCOCC(C)(C)COCCOC1 | CCCCCCCCCCCCC1(CC2=CC(=O)C=CC2=O)COCCOCC(C)(C)COCCOC1 | null | [O-2].[O-2].[Mn+4] | ClCCl | Oxidation | OtherReaction | 8e080e257c835909f04b22de1d62278b6e13d1c2ea092be950200c29bbf9740a | a6c6a9201eef9656e2a53a6d102761f5982be5a6ba4b17f7fdbbc6d73ced01df | O=C1C=CC(=O)C(CC2COCCOCCCOCCOC2)=C1 | [C:1]-[C:2]-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[OH;D1;+0:6]):[cH;D2;+0:7]:[cH;D2;+0:8]:[c;H0;D3;+0:9]:1-[OH;D1;+0:10]>>[C:1]-[C:2]-[C;H0;D3;+0:3]1=[CH;D2;+0:4]-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-[CH;D2;+0:7]=[CH;D2;+0:8]-[C;H0;D3;+0:9]-1=[O;H0;D1;+0:10] | null | [] | null | null | 1 | HOUR | A solution of 67.6 g (129.3 mmol) of Compound 6 in 600 mL of dichloromethane was mixed with 50.6 g (581.9 mmol) of activated manganese dioxide. The heterogeneous mixture was stirred at room temperature for 1 hour. The insolubles were removed by filtration through Celite diatomaceous earth and the solvent removed. The o... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Aromatic alcohol | Ketone.Ketone | c1ccccc1 | C1=CCC=CC1 | C1=CCC=CC1.C1COCCOCCCOCCOC1 | null | [O-2].[O-2].[Mn+4].ClCCl | null | 1 | CCCCCCCCCCCCC1(Cc2cc(O)ccc2O)COCCOCC(C)(C)COCCOC1>[O-2].[O-2].[Mn+4].ClCCl>CCCCCCCCCCCCC1(CC2=CC(=O)C=CC2=O)COCCOCC(C)(C)COCCOC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6d9cce36bc1640beacc29f308680a163 | CCCCCCCCCCCCC1(Cc2ccccc2O)COCCOCC(C)(C)COCCOC1.CS(=O)(=O)c1cc([N+](=O)[O-])ccc1[N+]#N>>CCCCCCCCCCCCC1(Cc2cc(N=Nc3ccc([N+](=O)[O-])cc3S(C)(=O)=O)ccc2O)COCCOCC(C)(C)COCCOC1 | C(CCCCCCCCCCC)C1(COCCOCC(COCCOC1)(C)C)CC1=C(C=CC=C1)O.F[P-](F)(F)(F)(F)F.CS(=O)(=O)C1=C(C=CC(=C1)[N+](=O)[O-])[N+]#N>>C(CCCCCCCCCCC)C1(COCCOCC(COCCOC1)(C)C)CC1=C(C=CC(=C1)N=NC1=C(C=C(C=C1)[N+](=O)[O-])S(=O)(=O)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][C:13]1([CH2:14][c:15]2[cH:16][cH:17][cH:33][cH:34][c:35]2[OH:36])[CH2:37][O:38][CH2:39][CH2:40][O:41][CH2:42][C:43]([CH3:44])([CH3:45])[CH2:46][O:47][CH2:48][CH2:49][O:50][CH2:51]1.[N:18]#[N+:19][c:20]1[cH:21][cH:22][c:23]([N+:24](=... | CCCCCCCCCCCCC1(Cc2ccccc2O)COCCOCC(C)(C)COCCOC1.CS(=O)(=O)c1cc([N+](=O)[O-])ccc1[N+]#N | CCCCCCCCCCCCC1(Cc2cc(N=Nc3ccc([N+](=O)[O-])cc3S(C)(=O)=O)ccc2O)COCCOCC(C)(C)COCCOC1 | null | null | C(C)(=O)O.O.O1CCCC1 | Functional Group Addition | OtherReaction | 1806c1538219ad87d28be4617a67fcd9909e935b7ee0e5872f99c23fe8ccecff | 2c6cd95d4efa78d9d3de76e13585ebc8f102df9229b31c028b4deed5aad0dd25 | c1ccc(N=Nc2cccc(CC3COCCOCCCOCCOC3)c2)cc1 | [N;H0;D1;+0:1]#[N+;H0;D2:2]-[c:3](:[c:4]):[c:5].[c:6]:[c:7]:[cH;D2;+0:8]:[c:9]:[c:10]>>[c:6]:[c:7]:[c;H0;D3;+0:8](-[N;H0;D2;+0:1]=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]):[c:9]:[c:10] | 4.9 | [{"value": 4.7, "product": "C(CCCCCCCCCCC)C1(COCCOCC(COCCOC1)(C)C)CC1=C(C=CC(=C1)N=NC1=C(C=C(C=C1)[N+](=O)[O-])S(=O)(=O)C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 4.9, "product": "C(CCCCCCCCCCC)C1(COCCOCC(COCCOC1)(C)C)CC1=C(C=CC(=C1)N=NC1=C(C=C(C=C1)[N+](=O)[O-])S(=O)(=O)C)O", "details": "CALCULAT... | null | null | 16 | HOUR | To a solution of 3.1 g (6.1 mmol) of Compound 15 in 50 cc acetic acid at 5° C. was added a solution of 3.0 g (8.0 mmol) of 2-methylsulfonyl-4-nitrophenyldiazonium hexafluorophosphate in 25 cc water and 75 cc tetrahydrofuran. The suspension was stirred at room temperature for 16 hours. The product was extracted into eth... | 10.6084/m9.figshare.5104873.v1 | null | null | Diazene | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.C1COCCOCCCOCCOC1 | null | C(C)(=O)O.O.O1CCCC1 | null | 16 | CCCCCCCCCCCCC1(Cc2ccccc2O)COCCOCC(C)(C)COCCOC1.CS(=O)(=O)c1cc([N+](=O)[O-])ccc1[N+]#N>C(C)(=O)O.O.O1CCCC1>CCCCCCCCCCCCC1(Cc2cc(N=Nc3ccc([N+](=O)[O-])cc3S(C)(=O)=O)ccc2O)COCCOCC(C)(C)COCCOC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9589a48d34f74be29e906b317fd0389c | Nc1ccc(-c2ccc(N)cc2)cc1.Nc1ccc(N)cc1>>Nc1ccc(N(c2ccc(N)cc2)c2ccc(-c3ccc(N(c4ccc(N)cc4)c4ccc(N)cc4)cc3)cc2)cc1 | C1=CC(=CC=C1N)N.C1(=CC=C(N)C=C1)C1=CC=C(N)C=C1>>NC1=CC=C(C=C1)N(C1=CC=C(C2=CC=C(N(C3=CC=C(C=C3)N)C3=CC=C(C=C3)N)C=C2)C=C1)C1=CC=C(C=C1)N | [c:7]1(-[c:18]2[cH:17][cH:39][c:26]([NH2:27])[cH:14][cH:38]2)[cH:8][cH:9][c:10]([NH2:11])[cH:12][cH:13]1.[NH2:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[cH:41][cH:42]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([N:6]([c:7]2[cH:8][cH:9][c:10]([NH2:11])[cH:12][cH:13]2)[c:14]2[cH:15][cH:16][c:17](-[c:18]3[cH:19][cH:20][c:21]([N:22]([c:23]4[... | Nc1ccc(-c2ccc(N)cc2)cc1.Nc1ccc(N)cc1 | Nc1ccc(N(c2ccc(N)cc2)c2ccc(-c3ccc(N(c4ccc(N)cc4)c4ccc(N)cc4)cc3)cc2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 7b59445b9dbd16b3d7e64ce4888acd423405a9e02cdcf33e3f8f3be9cf8ad8fd | 708aaf9b9308e90194297486ea8438895b5838a6d199d1df1fd3c78018c1732f | c1ccc(N(c2ccccc2)c2ccc(-c3ccc(N(c4ccccc4)c4ccccc4)cc3)cc2)cc1 | [N;D1;H2:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[cH;D2;+0:11]:[cH;D2;+0:12]:1.[NH2;D1;+0:13]-[c:14](:[c:15]):[c:16]>>[N;D1;H2:1]-[c;H0;D3;+0:2](:[c:17]:[c:18]):[c:19]:[c:20].[c:8]:[c:7]:[c;H0;D3;+0:6](-[N;H0;D3;+0:13](-[c:14](:[c:15]):[c:16])-[c;H0;D3;+0:... | null | [] | null | null | null | null | The same reaction as in Synthesis example 1 was carried out except for changing p-phenylenediamine used in Synthesis example 1 to benzidine to obtain 12 parts of orange tetrakis (p-aminophenyl)benzidine.
Conditions: See reaction.notes.procedure_details.
Workup: The same reaction; as in Synthesis example 1 | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Primary amine.Tertiary amine.Tertiary amine | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | null | null | null | Nc1ccc(-c2ccc(N)cc2)cc1.Nc1ccc(N)cc1>>Nc1ccc(N(c2ccc(N)cc2)c2ccc(-c3ccc(N(c4ccc(N)cc4)c4ccc(N)cc4)cc3)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f09896308b314dc9afd1bacf46b0ac34 | CCOC(=O)Cl.NCCC1(O)CCc2ccccc2C12CCCC2>>CCOC(=O)NCCC1(O)CCc2ccccc2C12CCCC2 | ClC(=O)OCC.NCCC1(C2(C3=CC=CC=C3CC1)CCCC2)O.C(C)N(CC)CC>>OC1(C2(C3=CC=CC=C3CC1)CCCC2)CCNC(OCC)=O | Cl[C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH2:6][CH2:7][CH2:8][C:9]1([OH:10])[CH2:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[C:19]12[CH2:20][CH2:21][CH2:22][CH2:23]2>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[NH:6][CH2:7][CH2:8][C:9]1([OH:10])[CH2:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[C:19]12[CH2:20][CH2:21... | CCOC(=O)Cl.NCCC1(O)CCc2ccccc2C12CCCC2 | CCOC(=O)NCCC1(O)CCc2ccccc2C12CCCC2 | null | null | C(Cl)Cl | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | c1ccc2c(c1)CCCC21CCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]-[C:5] | 98 | [{"value": 98.0, "product": "OC1(C2(C3=CC=CC=C3CC1)CCCC2)CCNC(OCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.9, "product": "OC1(C2(C3=CC=CC=C3CC1)CCCC2)CCNC(OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of the product from Example 9 (1.05 g, 4.28 mmol) and triethylamine (0.44 g, 4.35 mmol) in 10 mL of CH2Cl2 was cooled to 0° C. and ethyl chloroformate (0.47 g, 4.33 mmol) in 5 mL CH2Cl2 was added dropwise. The reaction was warmed to room temperature and washed with water. The aqueous phase was extracted with... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccc2c(c1)CCCC21CCCC1 | HCl | C(Cl)Cl | null | null | CCOC(=O)Cl.NCCC1(O)CCc2ccccc2C12CCCC2>C(Cl)Cl>CCOC(=O)NCCC1(O)CCc2ccccc2C12CCCC2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-01efe08bb86845ba8cb6c06c77c689fa | NCCC1(O)CCc2ccccc2C12CCCC2.O=C(Cl)OCC(Cl)(Cl)Cl>>O=C(NCCC1(O)CCc2ccccc2C12CCCC2)OCC(Cl)(Cl)Cl | ClC(COC(=O)Cl)(Cl)Cl.NCCC1(C2(C3=CC=CC=C3CC1)CCCC2)O.C(C)N(CC)CC>>OC1(C2(C3=CC=CC=C3CC1)CCCC2)CCNC(OCC(Cl)(Cl)Cl)=O | [NH2:3][CH2:4][CH2:5][C:6]1([OH:7])[CH2:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[C:16]12[CH2:17][CH2:18][CH2:19][CH2:20]2.Cl[C:2](=[O:1])[O:21][CH2:22][C:23]([Cl:24])([Cl:25])[Cl:26]>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][C:6]1([OH:7])[CH2:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[C:16]12[CH2:17][CH2:18... | NCCC1(O)CCc2ccccc2C12CCCC2.O=C(Cl)OCC(Cl)(Cl)Cl | O=C(NCCC1(O)CCc2ccccc2C12CCCC2)OCC(Cl)(Cl)Cl | null | null | C(Cl)Cl | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | c1ccc2c(c1)CCCC21CCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]-[C:5] | 78.1 | [{"value": 78.0, "product": "OC1(C2(C3=CC=CC=C3CC1)CCCC2)CCNC(OCC(Cl)(Cl)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.1, "product": "OC1(C2(C3=CC=CC=C3CC1)CCCC2)CCNC(OCC(Cl)(Cl)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | A solution of the product from Example 9 (0.88 g, 3.59 mmol) and triethylamine (0.40 g, 3.78 mmol) in 10 mL of CH2Cl2 was cooled to 0° C. and treated dropwise with 2,2,2-trichloroethylchloroformate (0.80 g, 3.78 mmol) in 2 mL CH2Cl2. The resulting solution was stirred at 0° C. for 30 minutes and warmed to room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccc2c(c1)CCCC21CCCC1 | HCl | C(Cl)Cl | 0 | 0.5 | NCCC1(O)CCc2ccccc2C12CCCC2.O=C(Cl)OCC(Cl)(Cl)Cl>C(Cl)Cl>O=C(NCCC1(O)CCc2ccccc2C12CCCC2)OCC(Cl)(Cl)Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-02b7b388594a45e995525bf702f7126b | Clc1ccc2c(Cl)ccnc2c1.Oc1ccc(F)cc1>>Fc1ccc(Oc2ccnc3cc(Cl)ccc23)cc1 | ClC1=CC=NC2=CC(=CC=C12)Cl.FC1=CC=C(C=C1)O>>FC1=CC=C(OC2=CC=NC3=CC(=CC=C23)Cl)C=C1 | Cl[c:7]1[cH:8][cH:9][n:10][c:11]2[cH:12][c:13]([Cl:14])[cH:15][cH:16][c:17]12.[F:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[cH:18][cH:19]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][n:10][c:11]3[cH:12][c:13]([Cl:14])[cH:15][cH:16][c:17]23)[cH:18][cH:19]1 | Clc1ccc2c(Cl)ccnc2c1.Oc1ccc(F)cc1 | Fc1ccc(Oc2ccnc3cc(Cl)ccc23)cc1 | null | null | C=1(C(=CC=CC1)C)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 499018af6792b58a137ac4495e0c20acdc548a3418ba695c815cb38084ffd839 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccnc3ccccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:6]:[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:7]:1:[c:8] | 615.9 | [{"value": 86.0, "product": "FC1=CC=C(OC2=CC=NC3=CC(=CC=C23)Cl)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 615.9, "product": "FC1=CC=C(OC2=CC=NC3=CC(=CC=C23)Cl)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a 50 mL flask equipped with a condenser, drying tube and thermometer, was added 1.98 g (0.01 moles) of 4,7-dichloroquinoline, 1.07 g (0.0015 moles) of polyDMAP™and 20 mL of xylene. The mixture was stirred to reswell the polymer and 1.57 g (0.0014 moles) of 4-fluorophenol were added. The reaction mixure was heated to... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1 | HCl | C=1(C(=CC=CC1)C)C | null | null | Clc1ccc2c(Cl)ccnc2c1.Oc1ccc(F)cc1>C=1(C(=CC=CC1)C)C>Fc1ccc(Oc2ccnc3cc(Cl)ccc23)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-083e912021ea4636b30489d9253b9684 | Clc1ccc2c(Cl)ccnc2c1.Oc1ccc(F)cc1>>Fc1ccc(Oc2ccnc3cc(Cl)ccc23)cc1 | ClC1=CC=NC2=CC(=CC=C12)Cl.FC1=CC=C(C=C1)O.N1(CCCC1)C1=CC=NC=C1>>FC1=CC=C(OC2=CC=NC3=CC(=CC=C23)Cl)C=C1 | Cl[c:7]1[cH:8][cH:9][n:10][c:11]2[cH:12][c:13]([Cl:14])[cH:15][cH:16][c:17]12.[F:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[cH:18][cH:19]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][n:10][c:11]3[cH:12][c:13]([Cl:14])[cH:15][cH:16][c:17]23)[cH:18][cH:19]1 | Clc1ccc2c(Cl)ccnc2c1.Oc1ccc(F)cc1 | Fc1ccc(Oc2ccnc3cc(Cl)ccc23)cc1 | null | null | C=1(C(=CC=CC1)C)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 499018af6792b58a137ac4495e0c20acdc548a3418ba695c815cb38084ffd839 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccnc3ccccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:6]:[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:7]:1:[c:8] | 649.9 | [{"value": 91.0, "product": "FC1=CC=C(OC2=CC=NC3=CC(=CC=C23)Cl)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 649.9, "product": "FC1=CC=C(OC2=CC=NC3=CC(=CC=C23)Cl)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a 50 mL flask equipped with a condenser, drying tube and thermometer, was added 1.98 g (0.01 moles) of 4,7-dichloroquinoline, 1.57 g (0.0014 moles) of 4-fluorophenol, 0.22 g (0.0015 moles) of 4-pyrrolidinopyridine and 20 mL of xylene. The reaction mixture was heated to reflux and reaction progress was monitored by T... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1 | HCl | C=1(C(=CC=CC1)C)C | null | 18 | Clc1ccc2c(Cl)ccnc2c1.Oc1ccc(F)cc1>C=1(C(=CC=CC1)C)C>Fc1ccc(Oc2ccnc3cc(Cl)ccc23)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e1035b9ffe964abea5e21dc8c9fb7b3c | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.O=C(COc1ccccc1)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(OS(=O)(=O)F)CS[C@H]12>>C=CC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)C(NC(=O)COc3ccccc3)[C@H]2SC1 | C(=C)[Sn](CCCC)(CCCC)CCCC.O(C1=CC=CC=C1)CC(=O)NC1[C@@H]2N(C(=C(CS2)OS(=O)(=O)F)C(=O)OC(C2=CC=CC=C2)C2=CC=CC=C2)C1=O>>O(C1=CC=CC=C1)CC(=O)NC1[C@@H]2N(C(=C(CS2)C=C)C(=O)OC(C2=CC=CC=C2)C2=CC=CC=C2)C1=O | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH:2]=[CH2:1].O=S(=O)(F)O[C:3]1=[C:4]([C:5](=[O:6])[O:7][CH:8]([c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[N:21]2[C:22](=[O:23])[CH:24]([NH:25][C:26](=[O:27])[CH2:28][O:29][c:30]3[cH:31][cH:32][cH:33][cH:34][cH:35]3)[C@H:36]2[S:37][CH2:38]1>>[... | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.O=C(COc1ccccc1)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(OS(=O)(=O)F)CS[C@H]12 | C=CC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)C(NC(=O)COc3ccccc3)[C@H]2SC1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | C(C)(=O)OCC.CN1C(CCC1)=O | C-C Coupling | OtherReaction | 67eba8952d4464cae7e07121b203292d2b8bccb1e2dcaa174b0cb724fd226a44 | 8229f2e290a81d798706abc950f1fa9d9c98a7ca1d13c9b7fa6b9f580d9aa5a6 | O=C(COc1ccccc1)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=CCS[C@H]12 | C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[CH;D2;+0:1]=[C;D1;H2:2].F-S(=O)(=O)-O-[C;H0;D3;+0:3]1=[C:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8])-[#7:9](-[C:10]=[O;D1;H0:11])-[C:12]-[#16:13]-[C:14]-1>>[C:8]-[#8:7]-[C:5](=[O;D1;H0:6])-[C:4]1=[C;H0;D3;+0:3](-[CH;D2;+0:1]=[C;D1;H2:2])-[C:14]-[#16:13]-[C:12]-[#7:9]-1-[C:10]=[O;... | 88.8 | [{"value": 85.0, "product": "O(C1=CC=CC=C1)CC(=O)NC1[C@@H]2N(C(=C(CS2)C=C)C(=O)OC(C2=CC=CC=C2)C2=CC=CC=C2)C1=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.8, "product": "O(C1=CC=CC=C1)CC(=O)NC1[C@@H]2N(C(=C(CS2)C=C)C(=O)OC(C2=CC=CC=C2)C2=CC=CC=C2)C1=O", "details": "CALCULATEDPERCENTYIELD", "is_desir... | null | null | 3 | MINUTE | A solution of palladium (II) acetate (3.6 mg, 0.016 mmol, 0.1 eq.) in 1-methyl-2-pyrrolidinone (2 mL) was treated with vinyl tri-n-butylstannane (58.4 mL, 0.2 mmol, 1.2 eq.) under an inert atmosphere and allowed to stir for 3 minutes. The resulting dark suspension was then treated with diphenylmethyl 7-phenoxyacetamido... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Vinyl.Tin | Enamine.Vinyl | C1=CN2CC[C@H]2SC1 | C1=CN2CC[C@H]2SC1 | c1ccccc1.c1ccccc1.C1=CN2CC[C@H]2SC1.c1ccccc1 | HF.Sn | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(C)(=O)OCC.CN1C(CCC1)=O | null | 0.05 | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.O=C(COc1ccccc1)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(OS(=O)(=O)F)CS[C@H]12>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(C)(=O)OCC.CN1C(CCC1)=O>C=CC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)C(NC(=O)COc3ccccc3)[C@H]2SC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c2b21fff05b941f38cbaf9f020481d88 | C/C=[CH]\[Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.O=C(COc1ccccc1)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(OS(=O)(=O)F)CS[C@H]12>>C/C=C\C1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)C(NC(=O)COc3ccccc3)[C@H]2SC1 | C(=C/C)/[Sn](CCCC)(CCCC)CCCC.O(C1=CC=CC=C1)CC(=O)NC1[C@@H]2N(C(=C(CS2)OS(=O)(=O)F)C(=O)OC(C2=CC=CC=C2)C2=CC=CC=C2)C1=O>>O(C1=CC=CC=C1)CC(=O)NC1[C@@H]2N(C(=C(CS2)\C=C/C)C(=O)OC(C2=CC=CC=C2)C2=CC=CC=C2)C1=O | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)/[CH:3]=[CH:2]\[CH3:1].O=S(=O)(F)O[C:4]1=[C:5]([C:6](=[O:7])[O:8][CH:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[N:22]2[C:23](=[O:24])[CH:25]([NH:26][C:27](=[O:28])[CH2:29][O:30][c:31]3[cH:32][cH:33][cH:34][cH:35][cH:36]3)[C@H:37]2[S:38][CH... | C/C=[CH]\[Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.O=C(COc1ccccc1)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(OS(=O)(=O)F)CS[C@H]12 | C/C=C\C1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)C(NC(=O)COc3ccccc3)[C@H]2SC1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | ClCCl | C-C Coupling | OtherReaction | 160aa54afc0e5af3c669cf3c80740ad875eeafe71c85a27744301f82bbccbd15 | a475964b87d2ef4c5698b1980466b9da951c3c0b64f664002f9d6da383a35778 | O=C(COc1ccccc1)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=CCS[C@H]12 | C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)/[CH;D2;+0:1]=[C:2]\[C;D1;H3:3].F-S(=O)(=O)-O-[C;H0;D3;+0:4]1=[C:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9])-[#7:10](-[C:11]=[O;D1;H0:12])-[C:13]-[#16:14]-[C:15]-1>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[C:5]1=[C;H0;D3;+0:4](/[CH;D2;+0:1]=[C:2]\[C;D1;H3:3])-[C:15]-[#16:14]-[C:13]-[#7:10... | 92.9 | [{"value": 89.0, "product": "O(C1=CC=CC=C1)CC(=O)NC1[C@@H]2N(C(=C(CS2)\\C=C/C)C(=O)OC(C2=CC=CC=C2)C2=CC=CC=C2)C1=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.9, "product": "O(C1=CC=CC=C1)CC(=O)NC1[C@@H]2N(C(=C(CS2)\\C=C/C)C(=O)OC(C2=CC=CC=C2)C2=CC=CC=C2)C1=O", "details": "CALCULATEDPERCENTYIELD", "... | null | null | 3 | MINUTE | A solution of palladium (II) acetate (3.6 mg, 0.016 mmole, 0.1 eq.) in dichloromethane (2 mL) was treated with Z-1-propenyl tri-n-butylstannane (66.2 mg, 0.2 mmole, 1.2 eq.) under an inert atmosphere and allowed to stir for 3 minutes. The resulting dark suspension was then treated with diphenylmethyl 7-phenoxyacetamido... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Tin | Enamine | C1=CN2CC[C@H]2SC1 | C1=CN2CC[C@H]2SC1 | c1ccccc1.c1ccccc1.C1=CN2CC[C@H]2SC1.c1ccccc1 | HF.Sn | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].ClCCl | null | 0.05 | C/C=[CH]\[Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.O=C(COc1ccccc1)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(OS(=O)(=O)F)CS[C@H]12>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].ClCCl>C/C=C\C1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)C(NC(=O)COc3ccccc3)[C@H]2SC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8261f787d18e44569a78042ee44a9160 | O=C(COc1ccccc1)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(O)CS[C@H]12.O=S(=O)(Cl)c1ccc(Br)cc1>>O=C(COc1ccccc1)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(OS(=O)(=O)c3ccc(Br)cc3)CS[C@H]12 | O(C1=CC=CC=C1)CC(=O)NC1[C@@H]2N(C(=C(CS2)O)C(=O)OC(C2=CC=CC=C2)C2=CC=CC=C2)C1=O.[H-].[Na+].BrC1=CC=C(C=C1)S(=O)(=O)Cl>>O(C1=CC=CC=C1)CC(=O)NC1[C@@H]2N(C(=C(CS2)OS(=O)(=O)C2=CC=C(C=C2)Br)C(=O)OC(C2=CC=CC=C2)C2=CC=CC=C2)C1=O | [O:1]=[C:2]([CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[NH:11][CH:12]1[C:13](=[O:14])[N:15]2[C:16]([C:17](=[O:18])[O:19][CH:20]([c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[c:27]3[cH:28][cH:29][cH:30][cH:31][cH:32]3)=[C:33]([OH:34])[CH2:45][S:46][C@H:47]12.Cl[S:35](=[O:36])(=[O:37])[c:38]1[cH:39][cH:40][c:41]([... | O=C(COc1ccccc1)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(O)CS[C@H]12.O=S(=O)(Cl)c1ccc(Br)cc1 | O=C(COc1ccccc1)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(OS(=O)(=O)c3ccc(Br)cc3)CS[C@H]12 | null | null | C(C)#N.[H][H] | Acylation | Formation of Sulfonic Esters | 5da4d330816d41221dac5ccfcb17cc7283f159f991810d3234e183c971c877c4 | a7be31b2844dda058c7c3aa56854ad4c914dd8646dc5e2d431f609f9ab031b83 | O=C(COc1ccccc1)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(OS(=O)(=O)c3ccccc3)CS[C@H]12 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[#16:7]-[C:8]-[C:9](-[OH;D1;+0:10])=[C:11](-[C:12](-[#8:13])=[O;D1;H0:14])-[#7:15]-[C:16]=[O;D1;H0:17]>>[#16:7]-[C:8]-[C:9](-[O;H0;D2;+0:10]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6])=[C:11](-[C:12](-[#8:13])=[O;D1;H0:14])-[#7:15]-[C... | 54.1 | [{"value": 54.0, "product": "O(C1=CC=CC=C1)CC(=O)NC1[C@@H]2N(C(=C(CS2)OS(=O)(=O)C2=CC=C(C=C2)Br)C(=O)OC(C2=CC=CC=C2)C2=CC=CC=C2)C1=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.1, "product": "O(C1=CC=CC=C1)CC(=O)NC1[C@@H]2N(C(=C(CS2)OS(=O)(=O)C2=CC=C(C=C2)Br)C(=O)OC(C2=CC=CC=C2)C2=CC=CC=C2)C1=O", "d... | 0 | CELSIUS | 5 | MINUTE | The title compound was prepared via a modification of the synthesis described in U.S. Pat. No. 3,985,737. A solution of 0.51 g (0.001 mole) of diphenylmethyl 7-phenoxyacetamido-3 -hydroxy-3-cephem- 4-carboxylate in 5 mL of acetonitrile was cooled to 0° C. under a nitrogen atmosphere. Then 0.030 g (0.001 mole) of sodium... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Sulfonyl halide | Sulfonate | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.C1=CN2CC[C@H]2SC1 | HCl | C(C)#N.[H][H] | 0 | 0.083333 | O=C(COc1ccccc1)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(O)CS[C@H]12.O=S(=O)(Cl)c1ccc(Br)cc1>C(C)#N.[H][H]>O=C(COc1ccccc1)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(OS(=O)(=O)c3ccc(Br)cc3)CS[C@H]12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d423bb0af2d64620abf46421b8a2f7ef | C/C=[CH]\[Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.O=C(COc1ccccc1)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(OS(=O)(=O)c3ccc(Br)cc3)CS[C@H]12>>C/C=C\C1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)C(NC(=O)COc3ccccc3)[C@H]2SC1 | O(C1=CC=CC=C1)CC(=O)NC1[C@@H]2N(C(=C(CS2)OS(=O)(=O)C2=CC=C(C=C2)Br)C(=O)OC(C2=CC=CC=C2)C2=CC=CC=C2)C1=O.C(=C/C)/[Sn](CCCC)(CCCC)CCCC.BrC1=CC=C(C=C1)S(=O)(=O)Cl>>O(C1=CC=CC=C1)CC(=O)NC1[C@@H]2N(C(=C(CS2)\C=C/C)C(=O)OC(C2=CC=CC=C2)C2=CC=CC=C2)C1=O | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)/[CH:3]=[CH:2]\[CH3:1].O=S(=O)(O[C:4]1=[C:5]([C:6](=[O:7])[O:8][CH:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[N:22]2[C:23](=[O:24])[CH:25]([NH:26][C:27](=[O:28])[CH2:29][O:30][c:31]3[cH:32][cH:33][cH:34][cH:35][cH:36]3)[C@H:37]2[S:38][CH2:... | C/C=[CH]\[Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.O=C(COc1ccccc1)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(OS(=O)(=O)c3ccc(Br)cc3)CS[C@H]12 | C/C=C\C1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)C(NC(=O)COc3ccccc3)[C@H]2SC1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | CN1C(CCC1)=O | C-C Coupling | OtherReaction | 37e41cffba8ac668bde391f540caf5d9c270d0ab2160981a195f860115c0841b | 8383f8d0bbaf97131fcc20a8fb4f619058433745d77ec5ce8e207bc38c340c6d | O=C(COc1ccccc1)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=CCS[C@H]12 | Br-c1:c:c:c(-S(=O)(=O)-O-[C;H0;D3;+0:1]2=[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[#7:7](-[C:8]=[O;D1;H0:9])-[C:10]-[#16:11]-[C:12]-2):c:c:1.C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)/[CH;D2;+0:13]=[C:14]\[C;D1;H3:15]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C:2]1=[C;H0;D3;+0:1](/[CH;D2;+0:13]=[C:14]\[C;D1;H3:15])-[C:12]-[... | null | [] | null | null | 20 | HOUR | To a mixture of 0.184 g (0.00025 mole) of the product of Procedure 6, 0.103 g (0.0003215 mole) of Z-1-propenyl-tri-n-butylstannane and 0.0064 g (0.000025 mole) of 4-bromobenzenesulfonyl chloride in 2.5 mL of 1-methyl-2-pyrrolidinone, under a nitrogen atmosphere, at room temperature was added 0.006 g (0.000025 mole) of ... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aromatic halide.Sulfonate.Tin | Enamine | C1=CN2CC[C@H]2SC1.c1ccccc1 | C1=CN2CC[C@H]2SC1 | c1ccccc1.c1ccccc1.C1=CN2CC[C@H]2SC1.c1ccccc1 | HBr.Sn | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CN1C(CCC1)=O | null | 20 | C/C=[CH]\[Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.O=C(COc1ccccc1)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(OS(=O)(=O)c3ccc(Br)cc3)CS[C@H]12>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CN1C(CCC1)=O>C/C=C\C1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)C(NC(=O)COc3ccccc3)[C@H]2SC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a5d5033460474ef09b7089853a326df4 | CC(=O)c1ccco1.COc1ccc(C=O)c(OC)c1.[OH-]>>COc1ccc(C(CC(=O)c2ccco2)CC(=O)c2ccco2)c(OC)c1 | COC1=C(C=O)C=CC(=C1)OC.[OH-].[K+].Cl.C(C)(=O)C=1OC=CC1>>O1C(=CC=C1)C(CC(CC(=O)C=1OC=CC1)C1=C(C=C(C=C1)OC)OC)=O | [CH3:16][C:17](=[O:18])[c:19]1[cH:20][cH:21][cH:22][o:23]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:11]([CH:9]=[O:10])[c:24]([O:25][CH3:26])[cH:27]1.[OH-:15]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][o:15]2)[CH2:16][C:17](=[O:18])[c:19]2[cH:20][cH:21][cH:22][o:23]2)[c:24]([O:... | CC(=O)c1ccco1.COc1ccc(C=O)c(OC)c1.[OH-] | COc1ccc(C(CC(=O)c2ccco2)CC(=O)c2ccco2)c(OC)c1 | null | null | CO.O | Aromatic Heterocycle Formation | OtherReaction | a82a1b2f946051e542c74241fe5372a5417c3f7324ebfef97b00a6fc52877822 | e1646497bb69536648e831497c90c3e74ad459ff066ba96f00e217e3294c42ff | O=C(CC(CC(=O)c1ccco1)c1ccccc1)c1ccco1 | [#8;a:1]:[c:2]-[C:3](-[CH3;D1;+0:4])=[O;D1;H0:5].[C;D1;H3:6]-[#8:7]-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[c:11]:[cH;D2;+0:12]:[c;H0;D3;+0:13]:1-[CH;D2;+0:14]=[O;D1;H0:15].[OH-;D0:16]>>[#8;a:1]:[c:2]-[C:3](=[O;D1;H0:5])-[CH2;D2;+0:4]-[C:17](-[C:18]-[C;H0;D3;+0:14](=[O;D1;H0:15])-[c;H0;D3;+0:13]1:[c:19]:[c:20]:[c:21]:[o;H0;D2;+0... | null | [] | 55 | CELSIUS | 8 | HOUR | Following the general methods outlined by Weller and Luellen (see above), to a solution of 16.6 g (0.1 mole) of 2,4-dimethoxybenzaldehyde 1 and 20 ml (0.2 mole) of 2-acetylfuran 2 in 100 ml of methanol was added 5.5 g of potassium hydroxide previously dissolved in a small amount of methanol. The resulting mixture was h... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone.Ether | Ketone.Ketone.Ether | c1ccccc1 | c1ccccc1.c1ccoc1 | c1ccccc1.c1ccoc1.c1ccoc1 | null | CO.O | 55 | 8 | CC(=O)c1ccco1.COc1ccc(C=O)c(OC)c1.[OH-]>CO.O>COc1ccc(C(CC(=O)c2ccco2)CC(=O)c2ccco2)c(OC)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-16c771509f2a408d9191b64cdb8e3d2d | CO.COc1cc(OCc2ccccc2)ccc1-c1cc(C(=O)O)nc(C(=O)O)c1>>COC(=O)c1cc(-c2ccc(OCc3ccccc3)cc2OC)cc(C(=O)OC)n1 | COC1=C(C=CC(=C1)OCC1=CC=CC=C1)C1=CC(=NC(=C1)C(=O)O)C(=O)O.CO.C(C(=O)Cl)(=O)Cl.Cl>>COC(=O)C1=NC(=CC(=C1)C1=C(C=C(C=C1)OCC1=CC=CC=C1)OC)C(=O)OC | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([O:12][CH2:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[cH:20][c:21]2[O:22][CH3:23])[cH:24][c:25]([C:26](=[O:27])[OH:28])[n:30]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([O:12][CH2:13][c:14]3[cH:15][cH:16][cH:17][c... | CO.COc1cc(OCc2ccccc2)ccc1-c1cc(C(=O)O)nc(C(=O)O)c1 | COC(=O)c1cc(-c2ccc(OCc3ccccc3)cc2OC)cc(C(=O)OC)n1 | null | CN(C)C=O | C(Cl)Cl.O | Protection | OtherReaction | 822daae55a346743d1340292c63f5c3519896c50ea9bc191c797511ef8ade007 | 1610f4d027acc3a508af39670faf7c6ca77bca08137335192290f34a61822d56 | c1ccc(COc2ccc(-c3ccncc3)cc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6]-[C:7](=[O;D1;H0:8])-[OH;D1;+0:9].[C;D1;H3:10]-[OH;D1;+0:11]>>[C;D1;H3:10]-[O;H0;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6]-[C:7](=[O;D1;H0:8])-[O;H0;D2;+0:9]-[C;D1;H3:12] | 65 | [{"value": 65.0, "product": "COC(=O)C1=NC(=CC(=C1)C1=C(C=C(C=C1)OCC1=CC=CC=C1)OC)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a suspension of 10 g (0.026 mole) of the diacid 22 in 100 ml of CH2Cl2 and 7 drops of DMF was added, at 0° C., in a dropwise fashion 12 ml (0.138 mole) of oxalyl chloride. After addition the mixture was allowed to come to room temperature with vigorous evolution of HCl gas and stirred for 2 hours. The resulting homo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Methanol | Ester.Ester | null | null | c1ccncc1.c1ccccc1.c1ccccc1 | null | CN(C)C=O.C(Cl)Cl.O | null | 2 | CO.COc1cc(OCc2ccccc2)ccc1-c1cc(C(=O)O)nc(C(=O)O)c1>CN(C)C=O.C(Cl)Cl.O>COC(=O)c1cc(-c2ccc(OCc3ccccc3)cc2OC)cc(C(=O)OC)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9b2830ab861241c3a58e06b4d4dabb73 | COC(=O)c1cc(-c2ccc(OCc3ccccc3)cc2OC)cc(C(=O)OC)n1>>COC(=O)c1cc(-c2ccc(O)cc2OC)cc(C(=O)OC)n1 | COC(=O)C1=NC(=CC(=C1)C1=C(C=C(C=C1)OCC1=CC=CC=C1)OC)C(=O)OC>>COC(=O)C1=NC(=CC(=C1)C1=C(C=C(C=C1)O)OC)C(=O)OC | c1ccc(C[O:12][c:11]2[cH:10][cH:9][c:8](-[c:7]3[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[n:23][c:18]([C:19](=[O:20])[O:21][CH3:22])[cH:17]3)[c:14]([O:15][CH3:16])[cH:13]2)cc1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([OH:12])[cH:13][c:14]2[O:15][CH3:16])[cH:17][c:18]([C:19](=[O:20])[O:21][CH3:2... | COC(=O)c1cc(-c2ccc(OCc3ccccc3)cc2OC)cc(C(=O)OC)n1 | COC(=O)c1cc(-c2ccc(O)cc2OC)cc(C(=O)OC)n1 | null | [Pd] | C(C)O | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(-c2ccncc2)cc1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | 89 | [{"value": 89.0, "product": "COC(=O)C1=NC(=CC(=C1)C1=C(C=C(C=C1)O)OC)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 8.9, "product": "COC(=O)C1=NC(=CC(=C1)C1=C(C=C(C=C1)O)OC)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 7 g (0.174 mole) of the diester 23 in 200 ml of ethanol was added 1.0 g of 10% Pd/C. The container for the resulting suspension was evacuated and filled with H2 (repeated three times) and kept under a positive atomosphere by means of a hydrogen-filled rubber bladder for 60 hours with very rapid stirrin... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccncc1.c1ccccc1 | Other | [Pd].C(C)O | null | null | COC(=O)c1cc(-c2ccc(OCc3ccccc3)cc2OC)cc(C(=O)OC)n1>[Pd].C(C)O>COC(=O)c1cc(-c2ccc(O)cc2OC)cc(C(=O)OC)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-728658d230cb49b7815fa4f092792817 | BrCc1cc(CBr)cc(CBr)c1.O=[N+]=O>>O=[N+]([O-])c1c(CBr)cc(CBr)cc1CBr | BrCC1=CC(=CC(=C1)CBr)CBr.F[B-](F)(F)F.O=[N+]=O.O>>BrCC1=C(C(=CC(=C1)CBr)CBr)[N+](=O)[O-] | [cH:4]1[c:5]([CH2:6][Br:7])[cH:8][c:9]([CH2:10][Br:11])[cH:12][c:13]1[CH2:14][Br:15].[O:1]=[N+:2]=[O:3]>>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([CH2:6][Br:7])[cH:8][c:9]([CH2:10][Br:11])[cH:12][c:13]1[CH2:14][Br:15] | BrCc1cc(CBr)cc(CBr)c1.O=[N+]=O | O=[N+]([O-])c1c(CBr)cc(CBr)cc1CBr | null | null | CC#N | Functional Group Addition | OtherReaction | 276ec2dfce0d9a25107ff9a7c7247f5a9b9ec7b55d27b2ac5d8644ca24f61ef2 | 5c75a9bf759be9717d985245c85c84dbfff904ea5287869736b84fdaa57f1e27 | c1ccccc1 | [C:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5](-[C:6]):[c:7].[O;D1;H0:8]=[N+;H0;D2:9]=[O;H0;D1;+0:10]>>[C:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[N+;H0;D3:9](-[O-;H0;D1:10])=[O;D1;H0:8]):[c:5](-[C:6]):[c:7] | 86.4 | [{"value": 86.0, "product": "BrCC1=C(C(=CC(=C1)CBr)CBr)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.4, "product": "BrCC1=C(C(=CC(=C1)CBr)CBr)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a solution of 5 g (0.014 mole) of the tribromide 8 in 100 ml of CH3CN was added, at room temperature and under argon atmosphere, in a dropwise fashion 3.72 g (0.028 mole) of nitronium tetrafluoroborate in 200 ml of CH3CN. The solution was then stirred for 20 minutes longer, poured into water and the mixture extracte... | 10.6084/m9.figshare.5104873.v1 | null | Nitroso.Nitroso | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | CC#N | null | 0.333333 | BrCc1cc(CBr)cc(CBr)c1.O=[N+]=O>CC#N>O=[N+]([O-])c1c(CBr)cc(CBr)cc1CBr |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1c4af60950e34e5ba3caea2d9484da0b | COC(=O)c1cc(-c2cc(S(=O)(=O)Cl)c(OC)cc2OC)cc(C(=O)OC)n1>>COc1ccc(-c2cc(C(=O)O)nc(C(=O)O)c2)c(OC)c1 | CCN(CC)CC.BrCC1=CC(=CC(=C1)CBr)CBr.C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NCCO.BrCC1=CC(=CC(=C1)CBr)CBr.COC(=O)C1=NC(=CC(=C1)C1=C(C=C(C(=C1)S(=O)(=O)Cl)OC)OC)C(=O)OC>>COC1=C(C=CC(=C1)OC)C1=CC(=NC(=C1)C(=O)O)C(=O)O | C[O:12][C:10]([c:9]1[cH:8][c:7](-[c:6]2[cH:5][c:4](S(=O)(=O)Cl)[c:3]([O:2][CH3:1])[cH:22][c:19]2[O:20][CH3:21])[cH:18][c:14]([C:15](=[O:16])[O:17]C)[n:13]1)=[O:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([C:10](=[O:11])[OH:12])[n:13][c:14]([C:15](=[O:16])[OH:17])[cH:18]2)[c:19]([O:20][CH3:21])[cH:22]1 | COC(=O)c1cc(-c2cc(S(=O)(=O)Cl)c(OC)cc2OC)cc(C(=O)OC)n1 | COc1ccc(-c2cc(C(=O)O)nc(C(=O)O)c2)c(OC)c1 | null | null | C(Cl)Cl.O.CO.C(Cl)(Cl)Cl | Reduction | OtherReaction | 0d9bf8bfe7d0a18fada4bcbec94d4f089e8dee8ad16619ee01b3b7f91e8e0183 | 269b2949df4a35609cf974ee1cfd8107cfa459bdc781a6835ee994df4d13402b | c1ccc(-c2ccncc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#7;a:5]:[c:6]-[C:7](=[O;D1;H0:8])-[O;H0;D2;+0:9]-C.Cl-S(=O)(=O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13](-[#8:14]):[c:15]>>[#8:14]-[c:13](:[c:15]):[cH;D2;+0:10]:[c:11]:[c:12].[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4]:[#7;a:5]:[c:6]-[C:7](=[O;D1;H0:8])-[OH;D1;+0:9] | null | [] | null | null | 30 | MINUTE | To a suspension of 0.5 g (0.0008 mole) of the amine-hydrochloride 8 in 20 ml of CH2Cl2 was added all at once 1.4 ml (0.01 mole) of Et3N. The mixture was then cooled to 5°-10° C. and 1.4 g (0.0032 mole) of the sulfonyl chloride 39 in 20 ml of CH2Cl2 was slowly added in a dropwise fashion. The reaction was then allowed t... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Sulfonyl halide | Carboxylic acid.Carboxylic acid | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccncc1 | HCl | C(Cl)Cl.O.CO.C(Cl)(Cl)Cl | null | 0.5 | COC(=O)c1cc(-c2cc(S(=O)(=O)Cl)c(OC)cc2OC)cc(C(=O)OC)n1>C(Cl)Cl.O.CO.C(Cl)(Cl)Cl>COc1ccc(-c2cc(C(=O)O)nc(C(=O)O)c2)c(OC)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-cbb94c59df7b4764bd7a91e9ed9e8888 | CCCC[C@@H](Br)C(=O)O.COCOC1CCN(C(=O)[C@@H](O)Cc2ccccc2)CC1>>CCCC[C@H](OCC[C@]1(C(=O)N2CCC(OCOC)CC2)C=CC=CC1)C(=O)O | COCOC1CCN(CC1)C(=O)[C@H](CC1=CC=CC=C1)O.[H-].[Na+].C1CCOC1.C1CCOC1.C1CCOC1.Br[C@@H](C(=O)O)CCCC.C1CCOC1>>COCOC1CCN(CC1)C(=O)[C@@]1(CC=CC=C1)CCO[C@H](C(=O)O)CCCC | Br[C@H:5]([CH2:4][CH2:3][CH2:2][CH3:1])[C:27](=[O:28])[OH:29].[OH:6][C@@H:9]([CH2:8][c:7]1[cH:22][cH:23][cH:24][cH:25][cH:26]1)[C:10](=[O:11])[N:12]1[CH2:13][CH2:14][CH:15]([O:16][CH2:17][O:18][CH3:19])[CH2:20][CH2:21]1>>[CH3:1][CH2:2][CH2:3][CH2:4][C@H:5]([O:6][CH2:7][CH2:8][C@:9]1([C:10](=[O:11])[N:12]2[CH2:13][CH2:1... | CCCC[C@@H](Br)C(=O)O.COCOC1CCN(C(=O)[C@@H](O)Cc2ccccc2)CC1 | CCCC[C@H](OCC[C@]1(C(=O)N2CCC(OCOC)CC2)C=CC=CC1)C(=O)O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | f9986e1066abeec14926410b5ca286b88f8c775731227b44ed34901ada297548 | 9b5f806834b6f9c74cdf1cbb6fa2220ed02cfe05046870520204e39c58bb7b7b | O=C(C1C=CC=CC1)N1CCCCC1 | Br-[C@H;D3;+0:1](-[C:2]-[C:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].[C:7]-[#7:8](-[C:9](=[O;D1;H0:10])-[C@@H;D3;+0:11](-[OH;D1;+0:12])-[C:13]-[c;H0;D3;+0:14]1:[cH;D2;+0:15]:[cH;D2;+0:16]:[cH;D2;+0:17]:[cH;D2;+0:18]:[cH;D2;+0:19]:1)-[C:20]>>[C:7]-[#7:8](-[C:9](=[O;D1;H0:10])-[C@;H0;D4;+0:11]1(-[C:13]-[CH2;D2;+0:14]-[O;H0;D2;... | 60 | [{"value": 60.0, "product": "COCOC1CCN(CC1)C(=O)[C@@]1(CC=CC=C1)CCO[C@H](C(=O)O)CCCC", "details": "PERCENTYIELD", "is_desired": false}] | 45 | CELSIUS | 1 | HOUR | 1(S)-(4-(Methoxymethoxy)piperidin-1-yl-carbonyl)-2-phenylethanol (European Patent Application No. EP364804, published Apr. 25, 1991) (43.13 g, 147.2 mmol) in 200 mL dry THF was added dropwise to the suspension of sodium hydride (60% dispersion in oil, 12.36 g, 309.1 mmol) in 136 mL dry THF and 22.7 mL DMF at 45° C. oil... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary alcohol | Ether.Conjugated diene | c1ccccc1 | C1=CCCC=C1 | C1CC[NH]CC1.C1=CCCC=C1 | Br- | CN(C)C=O | 45 | 1 | CCCC[C@@H](Br)C(=O)O.COCOC1CCN(C(=O)[C@@H](O)Cc2ccccc2)CC1>CN(C)C=O>CCCC[C@H](OCC[C@]1(C(=O)N2CCC(OCOC)CC2)C=CC=CC1)C(=O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9ef05d718e3f423da6bae4217b5ff8bd | NCCCN.O=C(OCc1ccccc1)ON1C(=O)CCC1=O>>NCCCNC(=O)OCc1ccccc1 | NCCCN.C(C1=CC=CC=C1)OC(=O)ON1C(CCC1=O)=O>>C(C1=CC=CC=C1)OC(=O)NCCCN | [NH2:1][CH2:2][CH2:3][CH2:4][NH2:5].O=C1CCC(=O)N1O[C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | NCCCN.O=C(OCc1ccccc1)ON1C(=O)CCC1=O | NCCCNC(=O)OCc1ccccc1 | null | null | C(Cl)(Cl)Cl | Protection | OtherReaction | 90f1cd2cfb4916c247fdb0b8c4bcd653fe37fb375d251f3afd49969111cee737 | f7ec1d72774a3155b06d1cf24e018b58f69117ddf4d9559df84efc3ecef0f4d7 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4] | 80 | [{"value": 80.0, "product": "C(C1=CC=CC=C1)OC(=O)NCCCN", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.0, "product": "C(C1=CC=CC=C1)OC(=O)NCCCN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 8 | HOUR | 1,3-Diaminopropane (35.5 g, 0.48 mol) was dissolved in 300 mL CHCl3, and the solution was cooled to 0° C. A solution of N-(benzyloxycarbonyloxy)succinimide (4.5 g, 0.018 mol) in 150 mL CHCl3 was added dropwise over 6 h, with the internal temperature maintained below 10° C. After addition was complete, the reaction solu... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Tertiary amide.Tertiary amide.Primary amine | Carbamic ester | C1CCNC1 | null | c1ccccc1 | HO- | C(Cl)(Cl)Cl | 0 | 8 | NCCCN.O=C(OCc1ccccc1)ON1C(=O)CCC1=O>C(Cl)(Cl)Cl>NCCCNC(=O)OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-622c30d078094a8eb9dec49e03627d22 | CCC(C)(CO)NC(=O)OCc1ccccc1.[N-]=[N+]=[N-]>>CCC(C)(CN=[N+]=[N-])NC(=O)OCc1ccccc1 | N=[N+]=[N-].[O-]S(=O)(=O)[O-].[Mg+2].N(=NC(=O)OC(C)C)C(=O)OC(C)C.[N-]=[N+]=[N-].C(C1=CC=CC=C1)OC(=O)NC(CO)(CC)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>N(=[N+]=[N-])CC(CC)(C)NC(=O)OCC1=CC=CC=C1 | O[CH2:5][C:3]([CH2:2][CH3:1])([CH3:4])[NH:9][C:10](=[O:11])[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[N-:6]=[N+:7]=[N-:8]>>[CH3:1][CH2:2][C:3]([CH3:4])([CH2:5][N:6]=[N+:7]=[N-:8])[NH:9][C:10](=[O:11])[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | CCC(C)(CO)NC(=O)OCc1ccccc1.[N-]=[N+]=[N-] | CCC(C)(CN=[N+]=[N-])NC(=O)OCc1ccccc1 | null | null | CCOC(=O)C.CCCCCC.C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | b6ef7629d0f9b9d1438b20ee6805124558e67d10777a15184211800dd3e8b973 | a446353c66aa2c48beeb0e3765234578855c107c1200bfc64cebc8b68d490616 | c1ccccc1 | O-[CH2;D2;+0:1]-[C:2](-[C:3])(-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7].[N-;H0;D1:8]=[#7;+:9]=[N;-;D1;H0:10]>>[C:3]-[C:2](-[C;D1;H3:4])(-[#7:5]-[C:6]=[O;D1;H0:7])-[CH2;D2;+0:1]-[N;H0;D2;+0:8]=[#7;+:9]=[N;-;D1;H0:10] | null | [] | 0 | CELSIUS | 1 | HOUR | 2-(Benyloxycarbonylamino)-2-methyl-1-butanol (1.358 g, 5.722 mmol) and triphenylphosphine (1.800 g, 6.86 mmol) were dissolved in 10 mL CH2Cl2, and the resulting solution was cooled to 0° C. A solution of hydrazoic acid (prepared from sodium azide (1.30 g, 20.0 mmol), 0.533 mL concentrated sulfuric acid and 1.3 mL water... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Azide | null | null | c1ccccc1 | HO- | CCOC(=O)C.CCCCCC.C(Cl)Cl | 0 | 1 | CCC(C)(CO)NC(=O)OCc1ccccc1.[N-]=[N+]=[N-]>CCOC(=O)C.CCCCCC.C(Cl)Cl>CCC(C)(CN=[N+]=[N-])NC(=O)OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-86be50e43ce8445287687f9a0c4a1bac | CC(C)=C1C[C@H](O)[C@H](CC2CCCCC2)NC1=O>>CC(C)[C@@H]1C[C@H](O)[C@H](C2CCCCC2)NC1=O | C1(CCCCC1)C[C@H]1[C@H](CC(C(N1)=O)=C(C)C)O>>C1(CCCCC1)[C@H]1[C@H](C[C@H](C(N1)=O)C(C)C)O | C1([CH2:9][C@H:8]2[C@@H:6]([OH:7])[CH2:5][C:4](=[C:2]([CH3:1])[CH3:3])[C:16](=[O:17])[NH:15]2)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1>>[CH3:1][CH:2]([CH3:3])[C@@H:4]1[CH2:5][C@H:6]([OH:7])[C@H:8]([CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[NH:15][C:16]1=[O:17] | CC(C)=C1C[C@H](O)[C@H](CC2CCCCC2)NC1=O | CC(C)[C@@H]1C[C@H](O)[C@H](C2CCCCC2)NC1=O | null | [Pd] | C(C)(=O)OCC | Miscellaneous | OtherReaction | 991a348c41662c029ddb376b9f1a188f98cd62eb88df9b000ea2621c824cd773 | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1CCC[C@H](C2CCCCC2)N1 | [C;D1;H3:1]-[C;H0;D3;+0:2](-[C;D1;H3:3])=[C;H0;D3;+0:4]1-[C:5]-[C:6]-[C:7](-[CH2;D2;+0:8]-C2-[CH2;D2;+0:9]-[C:10]-[C:11]-[C:12]-[CH2;D2;+0:13]-2)-[#7:14]-[C:15]-1=[O;D1;H0:16]>>[C;D1;H3:1]-[CH;D3;+0:2](-[C;D1;H3:3])-[C@@H;D3;+0:4]1-[C:5]-[C:6]-[C:7](-[CH;D3;+0:8]2-[CH2;D2;+0:9]-[C:10]-[C:11]-[C:12]-[CH2;D2;+0:13]-2)-[#... | null | [] | null | null | null | null | A solution of the product of Example 80e (24.7 g, 98.4 mmol) in 500 ml of ethyl acetate was treated with 2.5 g of dry Pd/C and hydrogenated at 4 atm for 4h at ambient temperature. The reaction mixture was filtered and concentrated to a white foamy solid which was taken on without further purification. mp 97°-99° C.; [α... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1CCNCC1.C1CCCCC1 | C1CCNCC1.C1CCCCC1 | C1CCNCC1.C1CCCCC1 | Other | [Pd].C(C)(=O)OCC | null | null | CC(C)=C1C[C@H](O)[C@H](CC2CCCCC2)NC1=O>[Pd].C(C)(=O)OCC>CC(C)[C@@H]1C[C@H](O)[C@H](C2CCCCC2)NC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6c6d592bcf1a42debe7854b152d5967a | CCC[CH2][Mg][Br].O=Cc1ccco1>>CCCCC(O)c1ccco1 | C(C1=CC=CO1)=O.C(CCC)[Mg]Br.[NH4+].[Cl-]>>O1C(=CC=C1)C(CCCC)O | [Br][Mg][CH2:4][CH2:3][CH2:2][CH3:1].[CH:5](=[O:6])[c:7]1[cH:8][cH:9][cH:10][o:11]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([OH:6])[c:7]1[cH:8][cH:9][cH:10][o:11]1 | CCC[CH2][Mg][Br].O=Cc1ccco1 | CCCCC(O)c1ccco1 | null | null | C1CCOC1 | C-C Coupling | Grignard from aldehyde to alcohol | fec51c6fbcca146daa523566f7e8d93ddaee19549cd7ca45d0ef939f0a2ea2fd | 38fa131ecaada942f85a297b49034b58ccef3f2e8ba6de5e28a59b5f4292ff1f | c1ccoc1 | [Br]-[Mg]-[CH2;D2;+0:1]-[C:2]-[C:3].[O;H0;D1;+0:4]=[CH;D2;+0:5]-[c:6](:[c:7]):[#8;a:8]:[c:9]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[CH;D3;+0:5](-[OH;D1;+0:4])-[c:6](:[c:7]):[#8;a:8]:[c:9] | null | [] | null | null | null | null | Freshly distilled furfural (233.5 g, 2.43 mol) was dissolved in 200 mL freshly distilled THF and added dropwise to a solution of butylmagnesium bromide (2.0 M in THF, 1460 mL, 2.92 mol) at 0° C. under dry nitrogen. After the addition was complete, the mixture was allowed to warm to room temperature overnight. The react... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Aldehyde | Secondary alcohol | null | null | c1ccoc1 | Br-.Mg | C1CCOC1 | null | null | CCC[CH2][Mg][Br].O=Cc1ccco1>C1CCOC1>CCCCC(O)c1ccco1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c3362f70087947e9a7caa72bda54863b | CCCCC(=O)c1ccco1>>CCCC[C@H](O)c1ccco1 | B#B.C(CCCC)(=O)C=1OC=CC1.O1B=NC=C1.Cl>>O1C(=CC=C1)[C@H](CCCC)O | [CH3:1][CH2:2][CH2:3][CH2:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][cH:10][o:11]1>>[CH3:1][CH2:2][CH2:3][CH2:4][C@H:5]([OH:6])[c:7]1[cH:8][cH:9][cH:10][o:11]1 | CCCCC(=O)c1ccco1 | CCCC[C@H](O)c1ccco1 | null | null | C1CCOC1.CO.CCOCC | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccoc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5](:[c:6]):[#8;a:7]:[c:8]>>[C:1]-[C:2]-[C@H;D3;+0:3](-[OH;D1;+0:4])-[c:5](:[c:6]):[#8;a:7]:[c:8] | 70 | [{"value": 70.0, "product": "O1C(=CC=C1)[C@H](CCCC)O", "details": "PERCENTYIELD", "is_desired": false}] | 10 | CELSIUS | null | null | 10.4 mmol (10.4 mL) of diborane (1 M solution in THF) was added dropwise in a period of 10 m at room temperature to a solution of 2-valeryl furan (2.62 g, 17.2 mmol) and 1.68 mmol (4.2 mL) of (3aR)-1,3,3-triphenyl pyrrolidino [1,2-c] [1,3,2] oxazaborole (see E. J. Corey et al. J. Am. Chem. Soc. 1987, 109, 7925-26, 0.4M... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccoc1 | null | C1CCOC1.CO.CCOCC | 10 | null | CCCCC(=O)c1ccco1>C1CCOC1.CO.CCOCC>CCCC[C@H](O)c1ccco1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c6c1fca572fe4e32bea0275f2d8b6a26 | CCCC[C@H](O)c1ccco1.O=C(O)CBr>>CCCCC(OCC(=O)O)c1ccco1 | [H-].[Na+].O1C(=CC=C1)[C@H](CCCC)O.BrCC(=O)O>>O1C(=CC=C1)C(OCC(=O)O)CCCC | [CH3:1][CH2:2][CH2:3][CH2:4][C@H:5]([OH:6])[c:11]1[cH:12][cH:13][cH:14][o:15]1.Br[CH2:7][C:8](=[O:9])[OH:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([O:6][CH2:7][C:8](=[O:9])[OH:10])[c:11]1[cH:12][cH:13][cH:14][o:15]1 | CCCC[C@H](O)c1ccco1.O=C(O)CBr | CCCCC(OCC(=O)O)c1ccco1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2e63de7b1f097c059f31781c5dec3b7812b761a1b3812b5238753f554cfa0846 | 9d3e82e8fa4f4bc62c1019e0bd869bdb0cf4748977f3c0b945b8ffdfc70126be | c1ccoc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;D1;H1:4].[C:5]-[C:6]-[C@H;D3;+0:7](-[OH;D1;+0:8])-[c:9](:[c:10]):[#8;a:11]:[c:12]>>[C:5]-[C:6]-[CH;D3;+0:7](-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;D1;H1:4])-[c:9](:[c:10]):[#8;a:11]:[c:12] | null | [] | 0 | CELSIUS | null | null | NaH (16.3 g, 680.9 mmol) and freshly distilled THF (170 mL) Were stirred at room temperature as (S)-1-(2-furyl)-1-pentanol ([α]25D -17.2°, 30.0 g, 46.0 mmol) in THF (170 mL) was added dropwise. After the addition was complete, the mixture was stirred for 15 m before cautiously heating to reflux for 1 h. The mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary alcohol | Ether | null | null | c1ccoc1 | HBr | C1CCOC1 | 0 | null | CCCC[C@H](O)c1ccco1.O=C(O)CBr>C1CCOC1>CCCCC(OCC(=O)O)c1ccco1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-98ddb6a92a0a4ff7b45cdbe2ae30430c | CCCCC(OCC(=O)O)c1ccco1>>CCCCC(OCC(=O)OC)c1ccco1 | [N+](=[N-])=C.O1C(=CC=C1)C(OCC(=O)O)CCCC.[OH-].[K+].CN(C(=N)N[N+](=O)[O-])N=O>>O1C(=CC=C1)C(OCC(=O)OC)CCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([O:6][CH2:7][C:8](=[O:9])[OH:10])[c:12]1[cH:13][cH:14][cH:15][o:16]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([O:6][CH2:7][C:8](=[O:9])[O:10][CH3:11])[c:12]1[cH:13][cH:14][cH:15][o:16]1 | CCCCC(OCC(=O)O)c1ccco1 | CCCCC(OCC(=O)OC)c1ccco1 | null | null | CCOCC | Miscellaneous | OtherReaction | 56520e0abb4535dce9a663824ca803b71c2c0dd72dfd246317d953596a987bd2 | 2ccc7a30191c2c171b49e8a0217bee87430687dd0f567141eca025a75b7e3136 | c1ccoc1 | [C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4]>>[C:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[C;D1;H3:5] | null | [] | null | null | null | null | Crude acid from example 84 (25 g, 118 mmol) was dissolved in ether and treated with excess diazomethane (generated by adding 1-methyl-3-nitro-1-nitrosoguanidine (MNNG) to a mixture of 40% KOH (aq) and ether at 0° C.). Excess diazomethane was quenched with acetic acid after 30 m. Vacuum distillation gave 18.8 g (70%): [... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1ccoc1 | Other | CCOCC | null | null | CCCCC(OCC(=O)O)c1ccco1>CCOCC>CCCCC(OCC(=O)OC)c1ccco1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ad9cc210d01d4d0d92c70ab465fa4799 | BrCc1ccccc1.CCCCC(OCC(=O)OC(c1ccccc1)c1ccccc1)c1ccco1>>CCCC[C@H](O[C@@H](Cc1ccccc1)C(=O)OC(c1ccccc1)c1ccccc1)c1ccco1 | C(C1=CC=CC=C1)Br.O1C(=CC=C1)C(OCC(=O)OC(C1=CC=CC=C1)C1=CC=CC=C1)CCCC.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>>C(C1=CC=CC=C1)[C@@H](C(=O)OC(C1=CC=CC=C1)C1=CC=CC=C1)O[C@@H](CCCC)C=1OC=CC1 | Br[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([O:6][CH2:7][C:15](=[O:16])[O:17][CH:18]([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1)[c:31]1[cH:32][cH:33][cH:34][o:35]1>>[CH3:1][CH2:2][CH2:3][CH2:4][C@H:5]([O:6][C@@H:7]([CH2:8][c:9]1[cH:... | BrCc1ccccc1.CCCCC(OCC(=O)OC(c1ccccc1)c1ccccc1)c1ccco1 | CCCC[C@H](O[C@@H](Cc1ccccc1)C(=O)OC(c1ccccc1)c1ccccc1)c1ccco1 | null | null | C1CCOC1.CN(C)P(=O)(N(C)C)N(C)C | C-C Coupling | OtherReaction | 796fea58c3dd096157de0ee3a241534b729bfe3e21ae3e32235c219d66dae5fc | 8ef4a7f3c2aa2c61ba42c1b7d8665a33daf968ae3eb9e2122661626a98ff3349 | O=C(OC(c1ccccc1)c1ccccc1)[C@H](Cc1ccccc1)OCc1ccco1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[#8:10]-[C:11]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C@@H;D3;+0:9](-[#8:10]-[C:11])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 0 | CELSIUS | null | null | Benzhydryl 4-(2-furyl)-3-oxaoctanoate (2.0 g, 5.28 mmol) was dissolved in 20 mL freshly distilled THF and cooled to -80°±5° C. under dry argon. Sodium bis(trimethylsilyl)-amide (1.0M in THF, 5.6 mL, 5.6 mmol) was slowly added keeping the temperature at -80°±5° C. After 15 m, freshly distilled and filtered (through basi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester.Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccoc1 | HBr | C1CCOC1.CN(C)P(=O)(N(C)C)N(C)C | 0 | null | BrCc1ccccc1.CCCCC(OCC(=O)OC(c1ccccc1)c1ccccc1)c1ccco1>C1CCOC1.CN(C)P(=O)(N(C)C)N(C)C>CCCC[C@H](O[C@@H](Cc1ccccc1)C(=O)OC(c1ccccc1)c1ccccc1)c1ccco1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-85107b868f4343088910de19a024cbd4 | BrCc1ccccc1.C1CCOC1.CCCCC(OCC(=O)OC(c1ccccc1)c1ccccc1)c1ccco1.C[Si](C)(C)[N-][Si](C)(C)C>>CCCCC(OCC(=O)OC(c1ccccc1)c1ccccc1)c1ccco1.CCCC[C@H](O[C@H](Cc1ccccc1)C(=O)OC(c1ccccc1)c1ccccc1)c1ccco1 | C1CCOC1.C(C1=CC=CC=C1)Br.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].O1C(=CC=C1)C(OCC(=O)OC(C1=CC=CC=C1)C1=CC=CC=C1)CCCC>>C(C1=CC=CC=C1)[C@H](C(=O)OC(C1=CC=CC=C1)C1=CC=CC=C1)O[C@@H](CCCC)C=1OC=CC1.O1C(=CC=C1)C(OCC(=O)OC(C1=CC=CC=C1)C1=CC=CC=C1)CCCC | Br[CH2:36][c:37]1[cH:38][cH:39][cH:40][cH:41][cH:42]1.[O:10]1[CH2:35][CH2:43][CH2:60][CH2:59]1.[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([O:6][CH2:7][C:8](=[O:9])[O:45][CH:46]([c:47]1[cH:48][cH:49][cH:50][cH:51][cH:52]1)[c:53]1[cH:54][cH:55][cH:56][cH:57][cH:58]1)[c:24]1[cH:25][cH:26][cH:62][o:63]1.[N-]([Si]([CH3:11])([CH3:12... | BrCc1ccccc1.C1CCOC1.CCCCC(OCC(=O)OC(c1ccccc1)c1ccccc1)c1ccco1.C[Si](C)(C)[N-][Si](C)(C)C | CCCCC(OCC(=O)OC(c1ccccc1)c1ccccc1)c1ccco1.CCCC[C@H](O[C@H](Cc1ccccc1)C(=O)OC(c1ccccc1)c1ccccc1)c1ccco1 | null | null | CN(C)P(=O)(N(C)C)N(C)C | Aromatic Heterocycle Formation | OtherReaction | 7c60e600fc7752f5f072b648ee44370457581b73a772d9bd30ab1c7fcea689de | 43f79a516217ddbf42d742f13759e3245ac5815b86c63e06b09cb7fc320df01d | O=C(COCc1ccco1)OC(c1ccccc1)c1ccccc1.O=C(OC(c1ccccc1)c1ccccc1)[C@@H](Cc1ccccc1)OCc1ccco1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH2;D2;+0:5]1-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[O;H0;D2;+0:9]-1.[CH3;D1;+0:10]-[Si](-[CH3;D1;+0:11])(-[CH3;D1;+0:12])-[N-]-[Si](-[CH3;D1;+0:13])(-[CH3;D1;+0:14])-[CH3;D1;+0:15].[C:16]-[C:17](-[#8:18]-[C:19]-[C;H0;D3;+0:20](=[O;D1;H0:21])-[O;H0;D2;+0:22]-[C:23](-[c:24])-[c:... | null | [] | null | null | null | null | Using the procedure in example 90 and (4S) benzhydryl 4-(2-furyl)-3-oxaoctanoate (5.0 g, 13.2 mmol), THF (50 mL), sodium bis(trimethylsilyl)amide (1.0M in THF, 14 mL, 14 mmol), and benzyl bromide (1.7 mL, 14 mmol) in 10 mL HMPA gave (2R,4S) benzhydryl 2-Benzyl-4-(2-furyl)-3-oxaoctanoate, 646.6 mg (10%) and 723 mg (12%)... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ether.Silyl protective group.Silyl protective group | Ester.Ester.Ether | C1CCOC1.c1ccoc1 | c1ccccc1.c1ccccc1.c1ccoc1.c1ccoc1 | c1ccccc1.c1ccccc1.c1ccoc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccoc1 | HBr | CN(C)P(=O)(N(C)C)N(C)C | null | null | BrCc1ccccc1.C1CCOC1.CCCCC(OCC(=O)OC(c1ccccc1)c1ccccc1)c1ccco1.C[Si](C)(C)[N-][Si](C)(C)C>CN(C)P(=O)(N(C)C)N(C)C>CCCCC(OCC(=O)OC(c1ccccc1)c1ccccc1)c1ccco1.CCCC[C@H](O[C@H](Cc1ccccc1)C(=O)OC(c1ccccc1)c1ccccc1)c1ccco1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c487bc368b6d4d0ab11ca0373808a940 | COC(=O)CC(=O)OC.Cc1ccccc1>>CC(=O)C=Cc1ccc(C)cc1 | C(CC(=O)OC)(=O)OC.C[O-].[Na+].C1(=CC=CC=C1)C>>CC1=CC=C(C=CC(C)=O)C=C1 | CO[C:2]([CH2:1][C:4](=O)OC)=[O:3].[cH:6]1[cH:7][cH:8][c:9]([CH3:10])[cH:11][cH:12]1>>[CH3:1][C:2](=[O:3])[CH:4]=[CH:5][c:6]1[cH:7][cH:8][c:9]([CH3:10])[cH:11][cH:12]1 | COC(=O)CC(=O)OC.Cc1ccccc1 | CC(=O)C=Cc1ccc(C)cc1 | null | null | null | C-C Coupling | OtherReaction | 8d85ac46602381ac081b39162f9d8eca42fcb98834561ecff1ad0ba1cfdd62ee | 53456c3e87e97f512921684f59b54573df1eee9d8c313db55cd612727f50bb31 | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=O)-O-C.[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[CH3;D1;+0:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D2;+0:4]=[C:10]-[c;H0;D3;+0:7](:[c:6]:[c:5]):[c:8]:[c:9] | null | [] | null | null | null | null | 132 g of dimethyl malonate are introduced into 1 liter of toluene and 180 g of 30% strength sodium methylate solution are added at room temperature. A crystal slurry results, to which 160 g of p-methylbenzalacetone are added dropwise, with vigorous stirring. In the course of 3 hours, the reaction mixture is heated, wit... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | null | null | COC(=O)CC(=O)OC.Cc1ccccc1>>CC(=O)C=Cc1ccc(C)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c5320739ecb94875895071e346290d87 | CC(=O)C=CC1CCCCC1.CCCC(=O)Cl.COC(=O)CC(=O)OC>>CCCC(=O)C1C(=O)CC(C2CCCCC2)CC1=O | [OH-].[Na+].C(CC(=O)OC)(=O)OC.C[O-].[Na+].C1(CCCCC1)C=CC(C)=O.C(CCC)(=O)Cl.Cl>>C(CCC)(=O)C1C(CC(CC1=O)C1CCCCC1)=O | [CH3:6][C:18]([CH:17]=[CH:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)=[O:19].Cl[C:4]([CH2:3][CH2:2][CH3:1])=[O:5].COC(=O)[CH2:9][C:7](OC)=[O:8]>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[CH:6]1[C:7](=[O:8])[CH2:9][CH:10]([CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)[CH2:17][C:18]1=[O:19] | CC(=O)C=CC1CCCCC1.CCCC(=O)Cl.COC(=O)CC(=O)OC | CCCC(=O)C1C(=O)CC(C2CCCCC2)CC1=O | null | null | C1(=CC=CC=C1)C.O | C-C Coupling | OtherReaction | e639475b924337c5181658d8a90a476ce491ff68027c341ba066aa3a55bb19e7 | 47470a729eeccda5bfeca983e4a619ea5fd51226dabbab763f38b7a3cc65932e | O=C1CC(=O)CC(C2CCCCC2)C1 | C-O-C(=O)-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-O-C.Cl-[C;H0;D3;+0:4](=[O;D1;H0:5])-[C:6]-[C:7].[C:8]-[C:9](-[CH;D2;+0:10]=[CH;D2;+0:11]-[C:12](-[CH3;D1;+0:13])=[O;D1;H0:14])-[C:15]>>[C:8]-[C:9](-[CH;D3;+0:10]1-[CH2;D2;+0:11]-[C:12](=[O;D1;H0:14])-[CH;D3;+0:13](-[C;H0;D3;+0:4](=[O;D1;H0:5])-[C:6]-[C:7])-[C;H0;D3;+... | 84.1 | [{"value": 84.0, "product": "C(CCC)(=O)C1C(CC(CC1=O)C1CCCCC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.1, "product": "C(CCC)(=O)C1C(CC(CC1=O)C1CCCCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 4 | HOUR | 132 g of dimethyl malonate, 180 g of 30% strength sodium methylate, 152 g of 1-cyclohexylbut-1-en-3-one and 106.5 g of butyryl chloride are reacted in 1 liter of toluene, in a manner similar to that described in Example 1. 5 g of 4-N,N-dimethylaminopyridine are added to the reaction mixture thus obtained and the batch ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ketone.Ester.Ester | Ketone.Ketone.Ketone | null | C1CCCCC1 | C1CCCCC1.C1CCCCC1 | HCl | C1(=CC=CC=C1)C.O | 100 | 4 | CC(=O)C=CC1CCCCC1.CCCC(=O)Cl.COC(=O)CC(=O)OC>C1(=CC=CC=C1)C.O>CCCC(=O)C1C(=O)CC(C2CCCCC2)CC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7b40b92986b142c0b4b761dffa4e4a2f | NNC(=O)c1ccc(O)cc1.Nc1ccccc1.O=C(Oc1ccccc1)c1ccc(O)cc1>>Oc1ccc(-c2nnc(-c3ccc(O)cc3)n2-c2ccccc2)cc1 | Cl.NC1=CC=CC=C1.OC1=CC=C(C(=O)NN)C=C1.C1(=CC=CC=C1)OC(C1=CC=C(C=C1)O)=O.C1(=CC=CC=C1)O>>OC1=CC=C(C=C1)C1=NN=C(N1C1=CC=CC=C1)C1=CC=C(C=C1)O | O=[C:9]([NH:8][NH2:7])[c:10]1[cH:11][cH:12][c:13]([OH:14])[cH:15][cH:16]1.[NH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1.O=[C:6](Oc1ccccc1)[c:5]1[cH:4][cH:3][c:2]([OH:1])[cH:25][cH:24]1>>[OH:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][n:8][c:9](-[c:10]3[cH:11][cH:12][c:13]([OH:14])[cH:15][cH:16]3)[n:17]2-[c:18]2[cH:19]... | NNC(=O)c1ccc(O)cc1.Nc1ccccc1.O=C(Oc1ccccc1)c1ccc(O)cc1 | Oc1ccc(-c2nnc(-c3ccc(O)cc3)n2-c2ccccc2)cc1 | null | null | null | Miscellaneous | OtherReaction | 3e9d0771548b24a3dc578df7b57aa1316c5a49b1e735951568a99ab9d6cf916b | e8af21e0f05f2b373585a67d65b8addb689f3c29b4af5933891ef079411717fe | c1ccc(-c2nnc(-c3ccccc3)n2-c2ccccc2)cc1 | O=[C;H0;D3;+0:1](-O-c1:c:c:c:c:c:1)-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].O=[C;H0;D3;+0:7](-[NH;D2;+0:8]-[NH2;D1;+0:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14].[NH2;D1;+0:15]-[c;H0;D3;+0:16](:[c:17]:[c:18]):[c:19]:[c:20]>>[c:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:7]1:[n;H0;D2;+0:8]:[n;H0;D2;+0:9]:[c;H0;D3;+0:... | 50 | [{"value": 50.0, "product": "OC1=CC=C(C=C1)C1=NN=C(N1C1=CC=CC=C1)C1=CC=C(C=C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.9, "product": "OC1=CC=C(C=C1)C1=NN=C(N1C1=CC=CC=C1)C1=CC=C(C=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 220 | CELSIUS | 2 | HOUR | Into a 500 ml three neck round bottom flask equipped with a magnetic stirbar, nitrogen inlet, glass stopper, and distillation head was placed 4-hydroxybenzoic hydrazide (60.9 g, 0.4 mol) and phenyl-4-hydroxybenzoate (85.7 g, 0.4 mol). The mixture was heated to approximately 220° C. by use of a Wood's metal bath. The so... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Ester.Primary amine | null | c1ccccc1 | c1nc[nH]n1 | c1ccccc1.c1nc[nH]n1.c1ccccc1.c1ccccc1 | HO- | null | 220 | 2 | NNC(=O)c1ccc(O)cc1.Nc1ccccc1.O=C(Oc1ccccc1)c1ccc(O)cc1>>Oc1ccc(-c2nnc(-c3ccc(O)cc3)n2-c2ccccc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-067a37df0148453b970f7e876cfd2a25 | Nc1ccc(Oc2ccc(N)c(N)c2)cc1N.O=C(Oc1ccccc1)c1ccc(O)cc1>>Oc1ccc(-c2nc3ccc(Oc4ccc5nc(-c6ccc(O)cc6)[nH]c5c4)cc3[nH]2)cc1 | NC=1C=C(C=CC1N)OC1=CC(=C(C=C1)N)N.C1(=CC=CC=C1)OC(C1=CC=C(C=C1)O)=O.C1(=CC=CC=C1)S(=O)(=O)C1=CC=CC=C1.C1(=CC=CC=C1)C>>O(C1=CC2=C(N=C(N2)C2=CC=C(C=C2)O)C=C1)C1=CC2=C(N=C(N2)C2=CC=C(C=C2)O)C=C1 | [NH2:7][c:8]1[cH:9][cH:10][c:11]([O:12][c:13]2[cH:14][cH:15][c:16]([NH2:17])[c:27]([NH2:26])[cH:28]2)[cH:29][c:30]1[NH2:31].O=[C:18]([O:1][c:2]1[cH:3][cH:4][cH:5][cH:32][cH:33]1)[c:19]1[cH:20][cH:21][c:22]([OH:23])[cH:24][cH:25]1>>[OH:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][c:11]([O:12][c:13]4[cH:14][... | Nc1ccc(Oc2ccc(N)c(N)c2)cc1N.O=C(Oc1ccccc1)c1ccc(O)cc1 | Oc1ccc(-c2nc3ccc(Oc4ccc5nc(-c6ccc(O)cc6)[nH]c5c4)cc3[nH]2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b911e48fe0a935f11d86453f9883acd47f0fc29a62d1c675eb70c867aec92c56 | 34a7f1192421a044c579c0d3f24e7e4d6654369b06ecfa22ca5e8f8321b21675 | c1ccc(-c2nc3ccc(Oc4ccc5nc(-c6ccccc6)[nH]c5c4)cc3[nH]2)cc1 | O=[C;H0;D3;+0:1](-[O;H0;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]:1)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13].[NH2;D1;+0:14]-[c:15](:[c:16]):[c:17](-[NH2;D1;+0:18]):[c:19].[NH2;D1;+0:20]-[c:21](:[c:22]):[c:23](-[NH2;D1;+0:24]):[c:25]>>[OH;D1;+0:2]-[c:3]1:[c:4]:[c:5]:[c;H0;D3;+0:6](-[c:26]2:[n;H0;D2;+0:24... | 30 | [{"value": 30.0, "product": "O(C1=CC2=C(N=C(N2)C2=CC=C(C=C2)O)C=C1)C1=CC2=C(N=C(N2)C2=CC=C(C=C2)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | A mixture of bis(3,4-diaminophenyl)ether (22.00 g, 0.096 mol), phenyl-4-hydroxybenzoate (41.00 g, 0.194 mol), diphenylsulfone (110.17 g), and toluene (135 ml) was heated under a nitrogen atmosphere for 3.5 hours at 150° C. The toluene was removed and the temperature increased to 250° C. and maintained for 1.5 hours. A ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine.Primary amine.Primary amine.Primary amine | Aromatic alcohol | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccc2[nH]cnc2c1.c1ccc2[nH]cnc2c1 | c1ccccc1.c1ccc2[nH]cnc2c1.c1ccc2[nH]cnc2c1.c1ccccc1 | null | null | 150 | null | Nc1ccc(Oc2ccc(N)c(N)c2)cc1N.O=C(Oc1ccccc1)c1ccc(O)cc1>>Oc1ccc(-c2nc3ccc(Oc4ccc5nc(-c6ccc(O)cc6)[nH]c5c4)cc3[nH]2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-cb39671eefbe47ab97af0a8c7bd6ff15 | C[C@@H]1CNC[C@H]1NC(=O)OC(C)(C)C.O=C(Cl)c1ccccc1>>C[C@@H]1CN(C(=O)c2ccccc2)C[C@H]1NC(=O)OC(C)(C)C | C(C)N(CC)CC.C(C1=CC=CC=C1)(=O)Cl.C(C)(C)(C)OC(=O)N[C@@H]1CNC[C@H]1C>>C(C)(C)(C)OC(=O)N[C@@H]1CN(C[C@H]1C)C(C1=CC=CC=C1)=O | [CH3:1][C@@H:2]1[CH2:3][NH:4][CH2:13][C@H:14]1[NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22].Cl[C:5](=[O:6])[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][C@H:14]1[NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])... | C[C@@H]1CNC[C@H]1NC(=O)OC(C)(C)C.O=C(Cl)c1ccccc1 | C[C@@H]1CN(C(=O)c2ccccc2)C[C@H]1NC(=O)OC(C)(C)C | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | 5ce41b3db1ff79b8dd0325761a92ce74d9b898070d3b61ae6f52ef2fb0fe31ed | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1CCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]1-[C:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:6]-[C:7]-[C:8]-[C:9]-1)-[c:3](:[c:4]):[c:5] | 97 | [{"value": 97.0, "product": "C(C)(C)(C)OC(=O)N[C@@H]1CN(C[C@H]1C)C(C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In the presence of triethylamine, 59 g of benzoyl chloride was reacted at room temperature with 81.4 g of trans-3-tert-butoxycarbonylamino-4-methylpyrrolidine in methylene chloride, whereby 120 g of trans-3-tert-butoxycarbonylamino-4-methyl-1-benzoylpyrrolidine (a) was obtained. Hydrochloric acid was then reacted at ro... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1 | HCl | C(Cl)Cl | null | null | C[C@@H]1CNC[C@H]1NC(=O)OC(C)(C)C.O=C(Cl)c1ccccc1>C(Cl)Cl>C[C@@H]1CN(C(=O)c2ccccc2)C[C@H]1NC(=O)OC(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2a852a07ea464fa89bf55a6c10dc6d5c | O=C(OCc1ccccc1)c1c(F)cc(F)c(F)c1F.OCc1ccccc1>>O=C(O)c1c(OCc2ccccc2)cc(F)c(F)c1F | C(C1=CC=CC=C1)O.FC1=C(C(=O)OCC2=CC=CC=C2)C(=CC(=C1F)F)F.O.[H-].[Na+]>>C(C1=CC=CC=C1)OC1=CC(=C(C(=C1C(=O)O)F)F)F | F[c:5]1[c:4]([C:2](=[O:1])[O:3]Cc2ccccc2)[c:19]([F:20])[c:17]([F:18])[c:15]([F:16])[cH:14]1.[OH:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[O:1]=[C:2]([OH:3])[c:4]1[c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][c:15]([F:16])[c:17]([F:18])[c:19]1[F:20] | O=C(OCc1ccccc1)c1c(F)cc(F)c(F)c1F.OCc1ccccc1 | O=C(O)c1c(OCc2ccccc2)cc(F)c(F)c1F | null | null | C(C)(=O)O.CCCCCC.C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 9d48094a081436f4e8572ec04094de4d166599c746a684c9c817617474d08f02 | 8a16c79d9023d6e1eac34a7a6cb858d135b938d7ebe110172115bd21e9860078 | c1ccc(COc2ccccc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-C-c1:c:c:c:c:c:1):[c:8].[OH;D1;+0:9]-[C:10]-[c:11]>>[O;D1;H0:6]=[C:5](-[OH;D1;+0:7])-[c:4](:[c:8]):[c;H0;D3;+0:1](-[O;H0;D2;+0:9]-[C:10]-[c:11]):[c:2]:[c:3] | 31.6 | [{"value": 31.6, "product": "C(C1=CC=CC=C1)OC1=CC(=C(C(=C1C(=O)O)F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 6.5 g of benzyl alcohol was dissolved in 150 ml of benzene. While the resultant solution was cooled with water, 2.4 g of sodium hydride (60%) was added and reacted. To the reaction mixture was added 15 g of benzyl 2,3,4,6-tetrafluorobenzoate, and stirred at room temperature for 1 hour. 3.6 g of acetic acid was added, f... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Primary alcohol | Carboxylic acid.Ether | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | C(C)(=O)O.CCCCCC.C1=CC=CC=C1 | null | 1 | O=C(OCc1ccccc1)c1c(F)cc(F)c(F)c1F.OCc1ccccc1>C(C)(=O)O.CCCCCC.C1=CC=CC=C1>O=C(O)c1c(OCc2ccccc2)cc(F)c(F)c1F |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-39ba3d3ec92e459f80ce36b757f83647 | COC(=O)c1c(F)cc(F)c(F)c1F>>COC(=O)c1c(N)cc(F)c(F)c1F | FC1=C(C(=O)OC)C(=CC(=C1F)F)F.C(C1=CC=CC=C1)N>>NC1=CC(=C(C(=C1C(=O)OC)F)F)F | F[c:6]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[c:13]([F:14])[c:11]([F:12])[c:9]([F:10])[cH:8]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([NH2:7])[cH:8][c:9]([F:10])[c:11]([F:12])[c:13]1[F:14] | COC(=O)c1c(F)cc(F)c(F)c1F | COC(=O)c1c(N)cc(F)c(F)c1F | null | null | C1=CC=CC=C1 | Functional Group Interconversion | OtherReaction | 0b3f36c6e96a844ac8c671a85ab317446ee29bfa735a32d39184f4616cac3a55 | 560c85d40afb1a57d77cf3258abf3be5bba829f35224f8687bf9a1d4c1f94bd9 | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8]):[c:9]>>[C;D1;H3:8]-[#8:7]-[C:5](=[O;D1;H0:6])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[N;D1;H2:10]):[c:2]:[c:3] | null | [] | null | null | 1.5 | HOUR | 60 g of methyl 2,3,4,6-tetrafluorobenzoate and 70 g of benzylamine were reacted under reflux for 1 hour in 400 ml of benzene. After the reaction mixture was allowed to cool down, it was washed successively with water, 1% hydrochloric acid and 1% aq. sodium carbonate, each in the amount of 600 ml. The reaction mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | C1=CC=CC=C1 | null | 1.5 | COC(=O)c1c(F)cc(F)c(F)c1F>C1=CC=CC=C1>COC(=O)c1c(N)cc(F)c(F)c1F |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-bba1b398f5164b93b56a82edcd1f84ce | O=c1ccoc2ccc(OCCCNCC3COc4cc5c(cc4O3)OCO5)cc12>>c1cc2c(cc1OCCCNCC1COc3cc4c(cc3O1)OCO4)CCCO2 | Cl.O1COC2=CC3=C(OCC(O3)CNCCCOC=3C=C4C(C=COC4=CC3)=O)C=C21.Cl.CC(C)O>>O1CCCC2=CC(=CC=C12)OCCCNCC1OC2=C(OC1)C=C1C(=C2)OCO1 | O=[c:26]1[c:4]2[c:3]([cH:2][cH:1][c:6]([O:7][CH2:8][CH2:9][CH2:10][NH:11][CH2:12][CH:13]3[CH2:14][O:15][c:16]4[cH:17][c:18]5[c:19]([cH:20][c:21]4[O:22]3)[O:23][CH2:24][O:25]5)[cH:5]2)[o:29][cH:28][cH:27]1>>[cH:1]1[cH:2][c:3]2[c:4]([cH:5][c:6]1[O:7][CH2:8][CH2:9][CH2:10][NH:11][CH2:12][CH:13]1[CH2:14][O:15][c:16]3[cH:17... | O=c1ccoc2ccc(OCCCNCC3COc4cc5c(cc4O3)OCO5)cc12 | c1cc2c(cc1OCCCNCC1COc3cc4c(cc3O1)OCO4)CCCO2 | null | [Pd] | CO | Reduction | OtherReaction | 6dad345603399266046e008fba48d21c660e0fe0e51569b1d41eae3180aa60d3 | 7ece147c6909fe307632f67c21e1517a1747c8ff389dff4b19e644c711d1d84d | c1cc2c(cc1OCCCNCC1COc3cc4c(cc3O1)OCO4)CCCO2 | O=[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[cH;D2;+0:3]:[o;H0;D2;+0:4]:[c:5](:[c:6]):[c:7]:1:[c:8]>>[c:6]:[c:5]1:[c:7](:[c:8])-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[O;H0;D2;+0:4]-1 | 56.3 | [{"value": 56.3, "product": "O1CCCC2=CC(=CC=C12)OCCCNCC1OC2=C(OC1)C=C1C(=C2)OCO1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | 6-[3-[[(6,7-Dihydro-1,3-dioxolo[4,5-g][1,4]benzodioxin-6-yl)methyl]amino]propoxy]chromen-4-one hydrochloride (0.9 g, 2.0 mmole), prepared in Example 5 above, was dissolved in 50 ml of methanol and 4N HCl/IPA (12.5 ml, 50 mmole) and 10% Palladium on Carbon (0.2 g) were added. The mixture was hydrogenated on a Parr appar... | 10.6084/m9.figshare.5104873.v1 | null | null | Ether | c1ccc2occcc2c1 | c1ccc2c(c1)CCCO2 | c1c2c(cc3c1OCO3)OCCO2.c1ccc2c(c1)CCCO2 | Other | [Pd].CO | null | 24 | O=c1ccoc2ccc(OCCCNCC3COc4cc5c(cc4O3)OCO5)cc12>[Pd].CO>c1cc2c(cc1OCCCNCC1COc3cc4c(cc3O1)OCO4)CCCO2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5865d24af6cd479aaec4ce67db420a22 | COc1ccc2c(c1)OC(CN)CO2.O=c1ccoc2cc(OCCCBr)ccc12>>COc1ccc2c(c1)OC(CNCCCOc1ccc3c(=O)ccoc3c1)CO2 | Cl.COC=1C=CC2=C(OC(CO2)CN)C1.BrCCCOC1=CC=C2C(C=COC2=C1)=O.C(C)(C)N(CC)C(C)C>>COC=1C=CC2=C(OC(CO2)CNCCCOC2=CC=C3C(C=COC3=C2)=O)C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[O:9][CH:10]([CH2:11][NH2:12])[CH2:28][O:29]2.Br[CH2:13][CH2:14][CH2:15][O:16][c:17]1[cH:18][cH:19][c:20]2[c:21](=[O:22])[cH:23][cH:24][o:25][c:26]2[cH:27]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[O:9][CH:10]([CH2:11][NH:12][CH2:13][CH2:14][CH2:15][O:16][c:1... | COc1ccc2c(c1)OC(CN)CO2.O=c1ccoc2cc(OCCCBr)ccc12 | COc1ccc2c(c1)OC(CNCCCOc1ccc3c(=O)ccoc3c1)CO2 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | O=c1ccoc2cc(OCCCNCC3COc4ccccc4O3)ccc12 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#8:4]-[C:5]-[C:6]-[NH2;D1;+0:7]>>[#8:4]-[C:5]-[C:6]-[NH;D2;+0:7]-[CH2;D2;+0:1]-[C:2]-[C:3] | 4.4 | [{"value": 4.4, "product": "COC=1C=CC2=C(OC(CO2)CNCCCOC2=CC=C3C(C=COC3=C2)=O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | 2,3-Dihydro-7-methoxy-1,4-benzodioxin-2-methanamine hydrochloride (4.0 g, 17 mmole), 7-(3-bromopropoxy)chromen-4-one (4.9 g, 17 mmole) and diisopropylethylamine (15.1 ml, 87 mmole) were combined in 150 ml of DMF and heated at 80° C. for 24 hours under a nitrogen atmosphere. The solvent was then removed and replaced wit... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccc2c(c1)OCCO2.c1ccc2cccoc2c1 | HBr | CN(C)C=O | 80 | null | COc1ccc2c(c1)OC(CN)CO2.O=c1ccoc2cc(OCCCBr)ccc12>CN(C)C=O>COc1ccc2c(c1)OC(CNCCCOc1ccc3c(=O)ccoc3c1)CO2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b5f1118b8c30426bbd0a88c29f75d946 | NCC1COc2ccc(O)cc2O1.O=c1ccoc2cc(OCCCBr)ccc12>>O=c1ccoc2cc(OCCCNCC3COc4ccc(O)cc4O3)ccc12 | Cl.OC=1C=CC2=C(OC(CO2)CN)C1.BrCCCOC1=CC=C2C(C=COC2=C1)=O.C(C)(C)N(CC)C(C)C>>OC=1C=CC2=C(OC(CO2)CNCCCOC2=CC=C3C(C=COC3=C2)=O)C1 | [NH2:13][CH2:14][CH:15]1[CH2:16][O:17][c:18]2[cH:19][cH:20][c:21]([OH:22])[cH:23][c:24]2[O:25]1.Br[CH2:12][CH2:11][CH2:10][O:9][c:8]1[cH:7][c:6]2[o:5][cH:4][cH:3][c:2](=[O:1])[c:28]2[cH:27][cH:26]1>>[O:1]=[c:2]1[cH:3][cH:4][o:5][c:6]2[cH:7][c:8]([O:9][CH2:10][CH2:11][CH2:12][NH:13][CH2:14][CH:15]3[CH2:16][O:17][c:18]4[... | NCC1COc2ccc(O)cc2O1.O=c1ccoc2cc(OCCCBr)ccc12 | O=c1ccoc2cc(OCCCNCC3COc4ccc(O)cc4O3)ccc12 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | O=c1ccoc2cc(OCCCNCC3COc4ccccc4O3)ccc12 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#8:4]-[C:5]-[C:6]-[NH2;D1;+0:7]>>[#8:4]-[C:5]-[C:6]-[NH;D2;+0:7]-[CH2;D2;+0:1]-[C:2]-[C:3] | 10.1 | [{"value": 10.1, "product": "OC=1C=CC2=C(OC(CO2)CNCCCOC2=CC=C3C(C=COC3=C2)=O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | 2,3-Dihydro-7-hydroxy-1,4-benzodioxin-2-methanamine hydrochloride (4.7 g, 22 mmole), 7-(3-bromopropoxy)chromen-4-one (6.1 g, 22 mmole) and diisopropylethylamine (18.8 ml, 108 mmole) were combined in 200 ml of DMF and heated at 80° C. for 24 hours under a nitrogen atmosphere. The solvent was then removed and replaced wi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccc2cccoc2c1.c1ccc2c(c1)OCCO2 | HBr | CN(C)C=O | 80 | null | NCC1COc2ccc(O)cc2O1.O=c1ccoc2cc(OCCCBr)ccc12>CN(C)C=O>O=c1ccoc2cc(OCCCNCC3COc4ccc(O)cc4O3)ccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f3e031aa403047fbaeb5992f3638bfd2 | COc1ccc(CC(C)=O)cc1OC.NCC(O)c1cccc(Cl)c1>>COc1ccc(CC(C)NCC(O)c2cccc(Cl)c2)cc1OC | ClC=1C=C(C=CC1)C(CN)O.COC=1C=C(C=CC1OC)CC(C)=O.C(#N)[BH3-].[Na+]>>ClC=1C=C(C=CC1)C(O)CNC(CC1=CC(=C(C=C1)OC)OC)C | O=[C:8]([CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:22]([O:23][CH3:24])[cH:21]1)[CH3:9].[NH2:10][CH2:11][CH:12]([OH:13])[c:14]1[cH:15][cH:16][cH:17][c:18]([Cl:19])[cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH:8]([CH3:9])[NH:10][CH2:11][CH:12]([OH:13])[c:14]2[cH:15][cH:16][cH:17][c:18]([Cl:19])[cH:20]2)[cH... | COc1ccc(CC(C)=O)cc1OC.NCC(O)c1cccc(Cl)c1 | COc1ccc(CC(C)NCC(O)c2cccc(Cl)c2)cc1OC | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 4940e8ed9a0db9bde699fdcdc3aff2cff0409c19478aa0ed1acfd98213338adf | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1ccc(CCNCCc2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[c:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3]-[c:4] | null | [] | null | null | null | null | In accordance with the above preferred reaction scheme 2-(3-chlorophenyl)-2-hydroxyethylamine 1, and 3,4-dimethoxyphenylacetone 2 are reacted with sodium cyanoborohydride in methanol, giving 3-chloroalpha-(((2-(3,4-dimethoxyphenyl)-1-methylethyl)amino)methyl) benzenemethanol 3 which is reacted with carbonyl diimidazole... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | Other | CO | null | null | COc1ccc(CC(C)=O)cc1OC.NCC(O)c1cccc(Cl)c1>CO>COc1ccc(CC(C)NCC(O)c2cccc(Cl)c2)cc1OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-da519b35e805446ebee7f87ca244eb1f | CCOC(=O)C(Br)(Br)C(=O)OCC.C[C@H](Cc1ccc(O)c(O)c1)N1C[C@@H](c2cccc(Cl)c2)OC1=O>>CCOC(=O)C1(C(=O)OCC)Oc2ccc(C[C@@H](C)N3C[C@@H](c4cccc(Cl)c4)OC3=O)cc2O1 | ClC=1C=C(C=CC1)[C@@H]1CN(C(O1)=O)[C@@H](CC1=CC(=C(C=C1)O)O)C.BrC(C(=O)OCC)(C(=O)OCC)Br.C([O-])([O-])=O.[K+].[K+]>>ClC=1C=C(C=CC1)[C@@H]1CN(C(O1)=O)[C@@H](CC1=CC2=C(OC(O2)(C(=O)OCC)C(=O)OCC)C=C1)C | Br[C:6](Br)([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:7](=[O:8])[O:9][CH2:10][CH3:11].[OH:12][c:13]1[cH:14][cH:15][c:16]([CH2:17][C@@H:18]([CH3:19])[N:20]2[CH2:21][C@@H:22]([c:23]3[cH:24][cH:25][cH:26][c:27]([Cl:28])[cH:29]3)[O:30][C:31]2=[O:32])[cH:33][c:34]1[OH:35]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1([C:7](=[O:8])[O:9]... | CCOC(=O)C(Br)(Br)C(=O)OCC.C[C@H](Cc1ccc(O)c(O)c1)N1C[C@@H](c2cccc(Cl)c2)OC1=O | CCOC(=O)C1(C(=O)OCC)Oc2ccc(C[C@@H](C)N3C[C@@H](c4cccc(Cl)c4)OC3=O)cc2O1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | af92e8ae1f27b7a1e6f478492a6f48fd98b71b8d2ef436c713fd3da904924b6f | 661a42d0ac7fd9eb76e924a46e5fae3d564c0d30f9b9482dcc715291d9bc27ca | O=C1O[C@H](c2ccccc2)CN1CCc1ccc2c(c1)OCO2 | Br-[C;H0;D4;+0:1](-Br)(-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9].[OH;D1;+0:10]-[c:11](:[c:12]):[c:13](-[OH;D1;+0:14]):[c:15]>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[C;H0;D4;+0:1]1(-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13](:[c:15])-[O;H0;D2;+0:14]-1 | null | [] | null | null | null | null | In accordance with the above preferred reaction scheme 2-(3-chlorophenyl)-2-hydroxyethylamine 1, and 3,4-dimethoxyphenylacetone 2 are reacted with sodium cyanoborohydride in methanol, giving 3-chloroalpha-(((2-(3,4-dimethoxyphenyl)-1-methylethyl)amino)methyl) benzenemethanol 3 which is reacted with carbonyl diimidazole... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Ester.Ester.Aromatic alcohol.Aromatic alcohol | Ester.Ester.Ether.Ether | null | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2.C1COC[NH]1.c1ccccc1 | HBr | CC(=O)C | null | null | CCOC(=O)C(Br)(Br)C(=O)OCC.C[C@H](Cc1ccc(O)c(O)c1)N1C[C@@H](c2cccc(Cl)c2)OC1=O>CC(=O)C>CCOC(=O)C1(C(=O)OCC)Oc2ccc(C[C@@H](C)N3C[C@@H](c4cccc(Cl)c4)OC3=O)cc2O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-cda2df2be4d44857bdab7b18d45916bd | CCOC(=O)C(Br)(Br)C(=O)OCC.C[C@H](Cc1ccc(O)c(O)c1)N1C[C@@H](c2cccc(Cl)c2)OC1=O>>CCOC(=O)C1(C(=O)OCC)Oc2ccc(C[C@@H](C)N3C[C@@H](c4cccc(Cl)c4)OC3=O)cc2O1 | ClC=1C=C(C=CC1)[C@@H]1CN(C(O1)=O)[C@@H](CC1=CC(=C(C=C1)O)O)C.BrC(C(=O)OCC)(C(=O)OCC)Br.C([O-])([O-])=O.[K+].[K+]>>ClC=1C=C(C=CC1)[C@@H]1CN(C(O1)=O)[C@@H](CC1=CC2=C(OC(O2)(C(=O)OCC)C(=O)OCC)C=C1)C | Br[C:6](Br)([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:7](=[O:8])[O:9][CH2:10][CH3:11].[OH:12][c:13]1[cH:14][cH:15][c:16]([CH2:17][C@@H:18]([CH3:19])[N:20]2[CH2:21][C@@H:22]([c:23]3[cH:24][cH:25][cH:26][c:27]([Cl:28])[cH:29]3)[O:30][C:31]2=[O:32])[cH:33][c:34]1[OH:35]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1([C:7](=[O:8])[O:9]... | CCOC(=O)C(Br)(Br)C(=O)OCC.C[C@H](Cc1ccc(O)c(O)c1)N1C[C@@H](c2cccc(Cl)c2)OC1=O | CCOC(=O)C1(C(=O)OCC)Oc2ccc(C[C@@H](C)N3C[C@@H](c4cccc(Cl)c4)OC3=O)cc2O1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | af92e8ae1f27b7a1e6f478492a6f48fd98b71b8d2ef436c713fd3da904924b6f | 661a42d0ac7fd9eb76e924a46e5fae3d564c0d30f9b9482dcc715291d9bc27ca | O=C1O[C@H](c2ccccc2)CN1CCc1ccc2c(c1)OCO2 | Br-[C;H0;D4;+0:1](-Br)(-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9].[OH;D1;+0:10]-[c:11](:[c:12]):[c:13](-[OH;D1;+0:14]):[c:15]>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[C;H0;D4;+0:1]1(-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13](:[c:15])-[O;H0;D2;+0:14]-1 | null | [] | null | null | null | null | More specifically, the chiral synthesis may be carried out by performing the synthetic reaction sequence outlined in Scheme III. L-DOPA 19 is treated with di-t-butyl-dicarbonate in dimethylformamide, giving (S)-N-(1-(1,1-dimethylethoxy)carbonyl)-3-hydroxy-L-tyrosine 20 which is reacted with methyl iodide and anhydrous ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Ester.Ester.Aromatic alcohol.Aromatic alcohol | Ester.Ester.Ether.Ether | null | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2.C1COC[NH]1.c1ccccc1 | HBr | CC(=O)C | null | null | CCOC(=O)C(Br)(Br)C(=O)OCC.C[C@H](Cc1ccc(O)c(O)c1)N1C[C@@H](c2cccc(Cl)c2)OC1=O>CC(=O)C>CCOC(=O)C1(C(=O)OCC)Oc2ccc(C[C@@H](C)N3C[C@@H](c4cccc(Cl)c4)OC3=O)cc2O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-463370cd2f4149d4a74c16289bb0ce5f | CCOC(=O)C(Br)(Br)C(=O)OCC.C[C@@H](Cc1ccc(O)c(O)c1)N1C[C@@H](c2cccc(Cl)c2)OC1=O>>CCOC(=O)C1(C(=O)OCC)Oc2ccc(C[C@@H](C)N3C[C@H](c4cccc(Cl)c4)OC3=O)cc2O1 | ClC=1C=C(C=CC1)[C@@H]1CN(C(O1)=O)[C@H](CC1=CC(=C(C=C1)O)O)C.BrC(C(=O)OCC)(C(=O)OCC)Br.C([O-])([O-])=O.[K+].[K+]>>ClC=1C=C(C=CC1)[C@H]1CN(C(O1)=O)[C@@H](CC1=CC2=C(OC(O2)(C(=O)OCC)C(=O)OCC)C=C1)C | Br[C:6](Br)([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:7](=[O:8])[O:9][CH2:10][CH3:11].[OH:12][c:13]1[cH:14][cH:15][c:16]([CH2:17][C@H:18]([CH3:19])[N:20]2[CH2:21][C@@H:22]([c:23]3[cH:24][cH:25][cH:26][c:27]([Cl:28])[cH:29]3)[O:30][C:31]2=[O:32])[cH:33][c:34]1[OH:35]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1([C:7](=[O:8])[O:9][... | CCOC(=O)C(Br)(Br)C(=O)OCC.C[C@@H](Cc1ccc(O)c(O)c1)N1C[C@@H](c2cccc(Cl)c2)OC1=O | CCOC(=O)C1(C(=O)OCC)Oc2ccc(C[C@@H](C)N3C[C@H](c4cccc(Cl)c4)OC3=O)cc2O1 | null | BrC(C(=O)OCC)(C(=O)OCC)Br | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | af92e8ae1f27b7a1e6f478492a6f48fd98b71b8d2ef436c713fd3da904924b6f | 661a42d0ac7fd9eb76e924a46e5fae3d564c0d30f9b9482dcc715291d9bc27ca | O=C1O[C@@H](c2ccccc2)CN1CCc1ccc2c(c1)OCO2 | Br-[C;H0;D4;+0:1](-Br)(-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9].[OH;D1;+0:10]-[c:11](:[c:12]):[c:13](-[OH;D1;+0:14]):[c:15]>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[C;H0;D4;+0:1]1(-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13](:[c:15])-[O;H0;D2;+0:14]-1 | 66.1 | [{"value": 66.1, "product": "ClC=1C=C(C=CC1)[C@H]1CN(C(O1)=O)[C@@H](CC1=CC2=C(OC(O2)(C(=O)OCC)C(=O)OCC)C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 0.8 g of the above oxazolidinone, 0.74 g of diethyl dibromomalonate, 1.2 g of anhydrous potassium carbonate and 20 ml of acetone are stirred overnight with the addition of a few drops of diethyl dibromomalonate. The mixture is filtered, washed with acetone and the combined filtrate and wash are evaporated ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Ester.Ester.Aromatic alcohol.Aromatic alcohol | Ester.Ester.Ether.Ether | null | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2.C1COC[NH]1.c1ccccc1 | HBr | BrC(C(=O)OCC)(C(=O)OCC)Br.CC(=O)C | null | null | CCOC(=O)C(Br)(Br)C(=O)OCC.C[C@@H](Cc1ccc(O)c(O)c1)N1C[C@@H](c2cccc(Cl)c2)OC1=O>BrC(C(=O)OCC)(C(=O)OCC)Br.CC(=O)C>CCOC(=O)C1(C(=O)OCC)Oc2ccc(C[C@@H](C)N3C[C@H](c4cccc(Cl)c4)OC3=O)cc2O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1c87a99897674504b9f67b900895e476 | CC(C)=O.CCOC(=O)C(Br)C(=O)OCC.O=C1NCCO1>>CCOC(=O)C1(C(=O)OCC)Oc2ccccc2O1 | O1C(NCC1)=O.BrC(C(=O)OCC)C(=O)OCC.C([O-])([O-])=O.[K+].[K+].CC(=O)C>>O1C(OC2=C1C=CC=C2)(C(=O)OCC)C(=O)OCC | C[C:15](=O)[CH3:14].Br[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:7](=[O:8])[O:9][CH2:10][CH3:11].O=[C:18]1N[CH2:16][CH2:17][O:19]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1([C:7](=[O:8])[O:9][CH2:10][CH3:11])[O:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[O:19]1 | CC(C)=O.CCOC(=O)C(Br)C(=O)OCC.O=C1NCCO1 | CCOC(=O)C1(C(=O)OCC)Oc2ccccc2O1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 94f07ca4b4604defe8f86efd1606f9449728efb37eea2bf833eda402a018515e | f0554a01e82e0f6e83f6b3f985aeef0a580a4d2833afa046490bc3fac37e3e64 | c1ccc2c(c1)OCO2 | Br-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9].C-[C;H0;D3;+0:10](=O)-[CH3;D1;+0:11].O=[C;H0;D3;+0:12]1-N-[CH2;D2;+0:13]-[CH2;D2;+0:14]-[O;H0;D2;+0:15]-1>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[C;H0;D4;+0:1]1(-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[#8:16]-[c:17]2:[cH;D2;+0:11]:[cH;D2;+0:10]:[... | null | [] | null | null | 8 | HOUR | A mixture of 240 mg of the above oxazolidinone, 234 mg of diethyl bromomalonate, 450 mg of anhydrous potassium carbonate and 10 ml of acetone is stirred overnight, filtered, washed with acetone and evaporated to a brown oil. The oil is purified by flash chromatography, eluting with 5 percent acetone in toluene. The pur... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Carbamic ester.Ketone.Ester.Ester.Ether | Ester.Ester.Ether.Ether | C1COCN1 | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | HBr | null | null | 8 | CC(C)=O.CCOC(=O)C(Br)C(=O)OCC.O=C1NCCO1>>CCOC(=O)C1(C(=O)OCC)Oc2ccccc2O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e5cdc5322a3f49ad962f9c48c672d656 | CN(C)C1CCCNc2ccccc21.O=C(Cl)c1ccc([N+](=O)[O-])cc1>>CN(C)C1CCCN(C(=O)c2ccc([N+](=O)[O-])cc2)c2ccccc21 | CN(C1CCCNC2=C1C=CC=C2)C.C([O-])([O-])=O.[K+].[K+].[N+](=O)([O-])C1=CC=C(C(=O)Cl)C=C1>>CN(C1CCCN(C2=C1C=CC=C2)C(C2=CC=C(C=C2)[N+](=O)[O-])=O)C | [CH3:1][N:2]([CH3:3])[CH:4]1[CH2:5][CH2:6][CH2:7][NH:8][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]21.Cl[C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19]1>>[CH3:1][N:2]([CH3:3])[CH:4]1[CH2:5][CH2:6][CH2:7][N:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19]2... | CN(C)C1CCCNc2ccccc21.O=C(Cl)c1ccc([N+](=O)[O-])cc1 | CN(C)C1CCCN(C(=O)c2ccc([N+](=O)[O-])cc2)c2ccccc21 | null | null | O.CC(=O)C | Acylation | N-alkylation of secondary amines with alkyl halides | 64413dd180580e9c8f2736c3a8c0c162d266e6033cf64f74e0aa763b2659218c | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1CCCCc2ccccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[c:9](:[c:10]):[c:11] | 97.1 | [{"value": 97.1, "product": "CN(C1CCCN(C2=C1C=CC=C2)C(C2=CC=C(C=C2)[N+](=O)[O-])=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-dimethylamino-2,3,4,5-tetrahydro-1H-benzazepine (50 g) in a mixture of acetone (400 ml) and water (200 ml) is added potassium carbonate (38.8 g), and thereto is added p-nitrobenzoyl chloride (40 g) with stirring under ice-cooling, and the mixture is stirred at room temperature overnight. To the react... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)CCCCN2 | c1ccc2c(c1)CCCC[NH]2 | c1ccccc1.c1ccc2c(c1)CCCC[NH]2 | HCl | O.CC(=O)C | null | null | CN(C)C1CCCNc2ccccc21.O=C(Cl)c1ccc([N+](=O)[O-])cc1>O.CC(=O)C>CN(C)C1CCCN(C(=O)c2ccc([N+](=O)[O-])cc2)c2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5863f8a43c894049b8ad42ad0415ff02 | CN(C)C1CCCN(C(=O)c2ccc([N+](=O)[O-])cc2)c2ccccc21>>CN(C)C1CCCN(C(=O)c2ccc(N)cc2)c2ccccc21 | CN(C1CCCN(C2=C1C=CC=C2)C(C2=CC=C(C=C2)[N+](=O)[O-])=O)C>>CN(C1CCCN(C2=C1C=CC=C2)C(C2=CC=C(C=C2)N)=O)C | O=[N+:15]([O-])[c:14]1[cH:13][cH:12][c:11]([C:9]([N:8]2[CH2:7][CH2:6][CH2:5][CH:4]([N:2]([CH3:1])[CH3:3])[c:23]3[c:18]2[cH:19][cH:20][cH:21][cH:22]3)=[O:10])[cH:17][cH:16]1>>[CH3:1][N:2]([CH3:3])[CH:4]1[CH2:5][CH2:6][CH2:7][N:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([NH2:15])[cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH... | CN(C)C1CCCN(C(=O)c2ccc([N+](=O)[O-])cc2)c2ccccc21 | CN(C)C1CCCN(C(=O)c2ccc(N)cc2)c2ccccc21 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1ccccc1)N1CCCCc2ccccc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 96 | [{"value": 96.0, "product": "CN(C1CCCN(C2=C1C=CC=C2)C(C2=CC=C(C=C2)N)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In ethanol (500 ml) is dispersed 10% Pd-C (5 g), and thereto is added 5-dimethylamino-1-(4-nitrobenzoyl)-2,3,4,5-tetrahydro-1H-benzazepine (64.1 g), and the mixture is subjected to catalytic reduction at ordinary room temperature under atmospheric pressure. After reduction, 10% Pd-C is removed by filtration, and the fi... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2c(c1)CCCC[NH]2 | Other | [Pd].C(C)O | null | null | CN(C)C1CCCN(C(=O)c2ccc([N+](=O)[O-])cc2)c2ccccc21>[Pd].C(C)O>CN(C)C1CCCN(C(=O)c2ccc(N)cc2)c2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c858891f9f9444f296084399c45e22a3 | COc1cc(NC(=O)c2ccccc2C)ccc1C(=O)N1CCCC(O)c2cc(Cl)ccc21.CSCC[C@H](NC(=O)OC(C)(C)C)C(=O)O>>COc1cc(NC(=O)c2ccccc2C)ccc1C(=O)N1CCCC(OC(=O)[C@H](CCSC)NC(=O)OC(C)(C)C)c2cc(Cl)ccc21 | OC1CCCN(C2=C1C=C(C=C2)Cl)C(C2=C(C=C(C=C2)NC(C2=C(C=CC=C2)C)=O)OC)=O.CN(C)C1=NC=CC=C1.Cl.CN(C)C1=NC=CC=C1.C(C)(C)(C)OC(=O)N[C@@H](CCSC)C(=O)O.C1(CCCCC1)N=C=NC1CCCCC1>>C(C)(C)(C)OC(=O)N[C@@H](CCSC)C(=O)OC1CCCN(C2=C1C=C(C=C2)Cl)C(C2=C(C=C(C=C2)NC(C2=C(C=CC=C2)C)=O)OC)=O | [CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[CH3:15])[cH:16][cH:17][c:18]1[C:19](=[O:20])[N:21]1[CH2:22][CH2:23][CH2:24][CH:25]([OH:26])[c:42]2[cH:43][c:44]([Cl:45])[cH:46][cH:47][c:48]21.O[C:27](=[O:28])[C@H:29]([CH2:30][CH2:31][S:32][CH3:33])[NH:34][C:35](=[O:36])[O:37][C... | COc1cc(NC(=O)c2ccccc2C)ccc1C(=O)N1CCCC(O)c2cc(Cl)ccc21.CSCC[C@H](NC(=O)OC(C)(C)C)C(=O)O | COc1cc(NC(=O)c2ccccc2C)ccc1C(=O)N1CCCC(OC(=O)[C@H](CCSC)NC(=O)OC(C)(C)C)c2cc(Cl)ccc21 | null | null | C(C)(=O)O.C(Cl)(Cl)Cl.CO | Acylation | Esterification of Carboxylic Acids | e916c5b009194e30c618975b40d7a233bfcf81339e65494c4e365f67cc5e011d | 12ba7405a548c6b1674f05065819c74f53f1b6165cd54e84e1f2f208042fe660 | O=C(Nc1ccc(C(=O)N2CCCCc3ccccc32)cc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[C:13]-[C:14](-[OH;D1;+0:15])-[c:16]>>[C:13]-[C:14](-[O;H0;D2;+0:15]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:1... | 121.2 | [{"value": 121.2, "product": "C(C)(C)(C)OC(=O)N[C@@H](CCSC)C(=O)OC1CCCN(C2=C1C=C(C=C2)Cl)C(C2=C(C=C(C=C2)NC(C2=C(C=CC=C2)C)=O)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 5-Hydroxy-7-chloro-1-[2-methoxy-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.7 g), dimethylaminopyridine (0.83 g) and dimethylaminopyridine hydrochloride (0.72 g) are dissolved in chloroform (15 ml), and thereto are added N-tert-butoxycarbonyl-L-methionine (0.56 g) and dicyclohexylcarbodiimide ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary alcohol | Ester | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCCC[NH]2 | HO- | C(C)(=O)O.C(Cl)(Cl)Cl.CO | null | 3 | COc1cc(NC(=O)c2ccccc2C)ccc1C(=O)N1CCCC(O)c2cc(Cl)ccc21.CSCC[C@H](NC(=O)OC(C)(C)C)C(=O)O>C(C)(=O)O.C(Cl)(Cl)Cl.CO>COc1cc(NC(=O)c2ccccc2C)ccc1C(=O)N1CCCC(OC(=O)[C@H](CCSC)NC(=O)OC(C)(C)C)c2cc(Cl)ccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3db121cfac504d159b1b06562cabf306 | O=C(O)Cc1ccccc1Cl.O=S(Cl)Cl>>O=C(Cl)Cc1ccccc1Cl | ClC1=C(C=CC=C1)CC(=O)O.S(=O)(Cl)Cl>>ClC1=C(C=CC=C1)CC(=O)Cl | O[C:2](=[O:1])[CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[Cl:11].O=S(Cl)[Cl:3]>>[O:1]=[C:2]([Cl:3])[CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[Cl:11] | O=C(O)Cc1ccccc1Cl.O=S(Cl)Cl | O=C(Cl)Cc1ccccc1Cl | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[c:5]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[c:5] | null | [] | null | null | 2 | HOUR | To 2-chlorophenylacetic acid (0.44 g) is added thionyl chloride (15 ml), and the mixture is stirred at room temperature for 2 hours. Thionyl chloride is distilled off, and the resultant is further distilled off by subjecting twice to azeotrophy with toluene. The resulting residue is dissolved in dichloromethane (10 ml)... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1 | HCl | null | null | 2 | O=C(O)Cc1ccccc1Cl.O=S(Cl)Cl>>O=C(Cl)Cc1ccccc1Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2aaa607f367b4114b06385b6e442d470 | CCOC(=O)CP(=O)(OCC)OCC.Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCCC(=O)c3cc(Cl)ccc32)c(C)c1>>CCOC(=O)C=C1CCCN(C(=O)c2ccc(NC(=O)c3ccccc3C)cc2C)c2ccc(Cl)cc21 | [H-].[Na+].C(C)OP(=O)(OCC)CC(=O)OCC.O=C1CCCN(C2=C1C=C(C=C2)Cl)C(C2=C(C=C(C=C2)NC(C2=C(C=CC=C2)C)=O)C)=O>>C(C)OC(=O)C=C1CCCN(C2=C1C=C(C=C2)Cl)C(C2=C(C=C(C=C2)NC(C2=C(C=CC=C2)C)=O)C)=O | CCOP(=O)(OCC)[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].O=[C:7]1[CH2:8][CH2:9][CH2:10][N:11]([C:12](=[O:13])[c:14]2[cH:15][cH:16][c:17]([NH:18][C:19](=[O:20])[c:21]3[cH:22][cH:23][cH:24][cH:25][c:26]3[CH3:27])[cH:28][c:29]2[CH3:30])[c:31]2[cH:32][cH:33][c:34]([Cl:35])[cH:36][c:37]21>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]... | CCOC(=O)CP(=O)(OCC)OCC.Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCCC(=O)c3cc(Cl)ccc32)c(C)c1 | CCOC(=O)C=C1CCCN(C(=O)c2ccc(NC(=O)c3ccccc3C)cc2C)c2ccc(Cl)cc21 | null | null | O1CCCC1 | C-C Coupling | Wittig with Phosphonium | 0f071c5d088734a3668468c108c63f4eebdb54435791854b689fbe85c99a4524 | 79a946b42eb7e7aee42e09efe41630192c1745e07085cd7f7f88cc7b599f9082 | [CH]=C1CCCN(C(=O)c2ccc(NC(=O)c3ccccc3)cc2)c2ccccc21 | C-C-O-P(=O)(-O-C-C)-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].O=[C;H0;D3;+0:6](-[C:7]-[C:8])-[c:9](:[c:10]):[c:11]-[#7:12]>>[#7:12]-[c:11]:[c:9](:[c:10])-[C;H0;D3;+0:6](=[CH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[C:7]-[C:8] | null | [] | null | null | null | null | To tetrahydrofuran (200 ml) is added sodium hydride (60%, 0.85 g), and thereto is added dropwise ethyl diethylphosphonoacetate (4.68 ml) with stirring under ice-cooling, and the mixture is further stirred under ice-cooling for 10 minutes. To the reaction mixture is added 5-oxo-7-chloro-1-[2-methyl-4-(2-methylbenzoylami... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ester | c1ccc2c(c1)CCCC[NH]2 | c1ccc2c(c1)CCCC[NH]2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCCC[NH]2 | HO- | O1CCCC1 | null | null | CCOC(=O)CP(=O)(OCC)OCC.Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCCC(=O)c3cc(Cl)ccc32)c(C)c1>O1CCCC1>CCOC(=O)C=C1CCCN(C(=O)c2ccc(NC(=O)c3ccccc3C)cc2C)c2ccc(Cl)cc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-be3698e1a0504a98b5ed49a7b8e68b9f | CCOC(=O)C=C1CCCN(C(=O)c2ccc(NC(=O)c3ccccc3C)cc2C)c2ccc(Cl)cc21>>CCOC(=O)CC1CCCN(C(=O)c2ccc(NC(=O)c3ccccc3C)cc2C)c2ccc(Cl)cc21 | C(C)OC(=O)C=C1CCCN(C2=C1C=C(C=C2)Cl)C(C2=C(C=C(C=C2)NC(C2=C(C=CC=C2)C)=O)C)=O.[BH4-].[Na+]>>C(C)OC(=O)CC1CCCN(C2=C1C=C(C=C2)Cl)C(C2=C(C=C(C=C2)NC(C2=C(C=CC=C2)C)=O)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[C:7]1[CH2:8][CH2:9][CH2:10][N:11]([C:12](=[O:13])[c:14]2[cH:15][cH:16][c:17]([NH:18][C:19](=[O:20])[c:21]3[cH:22][cH:23][cH:24][cH:25][c:26]3[CH3:27])[cH:28][c:29]2[CH3:30])[c:31]2[cH:32][cH:33][c:34]([Cl:35])[cH:36][c:37]21>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]1[CH2:8][... | CCOC(=O)C=C1CCCN(C(=O)c2ccc(NC(=O)c3ccccc3C)cc2C)c2ccc(Cl)cc21 | CCOC(=O)CC1CCCN(C(=O)c2ccc(NC(=O)c3ccccc3C)cc2C)c2ccc(Cl)cc21 | null | O.O.O.O.O.O.[Ni](Cl)Cl | O1CCCC1.CO | Reduction | Hydrogenation (double to single) | 65c294937a18f0bcd8c57100fa93b4fc8c207c3d98829714ec7712a3b8bd7de0 | 9a50abf8d2e4cd9195d7a0cadbe97483a261a81cf70b653cfddd5ecf76d383a6 | O=C(Nc1ccc(C(=O)N2CCCCc3ccccc32)cc1)c1ccccc1 | [#7:1]-[c:2]:[c:3](:[c:4])-[C;H0;D3;+0:5](=[CH;D2;+0:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10])-[C:11]-[C:12]>>[#7:1]-[c:2]:[c:3](:[c:4])-[CH;D3;+0:5](-[CH2;D2;+0:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10])-[C:11]-[C:12] | 43.2 | [{"value": 43.2, "product": "C(C)OC(=O)CC1CCCN(C2=C1C=C(C=C2)Cl)C(C2=C(C=C(C=C2)NC(C2=C(C=CC=C2)C)=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-Ethoxycarbonylmethylidene-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.30 g) and nickel chloride hexahydrate (0.55 g) are dissolved in a mixture of tetrahydrofuran/methanol (1:1) (30 ml), and to the mixture is added slowly sodium borohydride (0.26 g) with stirring under i... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | c1ccc2c(c1)CCCC[NH]2 | c1ccc2c(c1)CCCC[NH]2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCCC[NH]2 | null | O.O.O.O.O.O.[Ni](Cl)Cl.O1CCCC1.CO | null | null | CCOC(=O)C=C1CCCN(C(=O)c2ccc(NC(=O)c3ccccc3C)cc2C)c2ccc(Cl)cc21>O.O.O.O.O.O.[Ni](Cl)Cl.O1CCCC1.CO>CCOC(=O)CC1CCCN(C(=O)c2ccc(NC(=O)c3ccccc3C)cc2C)c2ccc(Cl)cc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-dc7d68fa76f84aebbe68d0076ffab1c1 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCCC(O)c3cc(Cl)ccc32)c(C)c1>>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCCC(OC(=O)[C@@H](N)C(C)C)c3cc(Cl)ccc32)c(C)c1 | OC1CCCN(C2=C1C=C(C=C2)Cl)C(C2=C(C=C(C=C2)NC(C2=C(C=CC=C2)C)=O)C)=O.CN(C)C1=NC=CC=C1.Cl.CN(C)C1=NC=CC=C1.C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)O.C1(CCCCC1)N=C=NC1CCCCC1>>N[C@@H](C(C)C)C(=O)OC1CCCN(C2=C1C=C(C=C2)Cl)C(C2=C(C=C(C=C2)NC(C2=C(C=CC=C2)C)=O)C)=O | O=C(OCc1ccccc1)[NH:26][C@H:25]([C:23](O)=[O:24])[CH:27]([CH3:28])[CH3:29].[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[N:17]2[CH2:18][CH2:19][CH2:20][CH:21]([OH:22])[c:30]3[cH:31][c:32]([Cl:33])[cH:34][cH:35][c:36]32)[c:37]([CH3:38])[cH:39]1>>[CH3:1][c:2]1[c... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCCC(O)c3cc(Cl)ccc32)c(C)c1 | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCCC(OC(=O)[C@@H](N)C(C)C)c3cc(Cl)ccc32)c(C)c1 | null | [Pd] | C(C)(=O)O.C(Cl)(Cl)Cl.CO.C(C)(=O)OCC | Acylation | OtherReaction | 2c76e343c45b7ee92c0bde24be04b20d4f03c30e0e1a1475114364c1d9034734 | d049f62045e9c4fca1379cc1d9834b97ce2bdeaad5d7209d97ba9cb0d8edbebd | O=C(Nc1ccc(C(=O)N2CCCCc3ccccc32)cc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[NH;D2;+0:5]-C(=O)-O-C-c1:c:c:c:c:c:1.[C:6]-[C:7](-[OH;D1;+0:8])-[c:9]>>[C:6]-[C:7](-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[NH2;D1;+0:5])-[c:9] | 38.5 | [{"value": 38.5, "product": "N[C@@H](C(C)C)C(=O)OC1CCCN(C2=C1C=C(C=C2)Cl)C(C2=C(C=C(C=C2)NC(C2=C(C=CC=C2)C)=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 7 | HOUR | To a solution of 5-hydroxy-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (1.0 g), dimethylaminopyridine (1.26 g) and dimethylaminopyridine hydrochloride (1.10 g) in chloroform (20 ml) are added N-benzyloxycarbonyl-L-valine (672 mg) and dicyclohexylcarbodiimide (1.42 g), and the... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Secondary alcohol | Ester.Primary amine | c1ccccc1 | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCCC[NH]2 | HO- | [Pd].C(C)(=O)O.C(Cl)(Cl)Cl.CO.C(C)(=O)OCC | null | 7 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCCC(O)c3cc(Cl)ccc32)c(C)c1>[Pd].C(C)(=O)O.C(Cl)(Cl)Cl.CO.C(C)(=O)OCC>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCCC(OC(=O)[C@@H](N)C(C)C)c3cc(Cl)ccc32)c(C)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8b0e6b9d18174370a977ef82358fad31 | COc1cc(NC(=O)c2ccccc2C)ccc1C(=O)N1CCCC(OC(=O)[C@H](CCSC)NC(=O)OC(C)(C)C)c2cc(Cl)ccc21>>COc1cc(NC(=O)c2ccccc2C)ccc1C(=O)N1CCCC(OC(=O)[C@@H](N)CCSC)c2cc(Cl)ccc21 | C(C)(C)(C)OC(=O)N[C@@H](CCSC)C(=O)OC1CCCN(C2=C1C=C(C=C2)Cl)C(C2=C(C=C(C=C2)NC(C2=C(C=CC=C2)C)=O)OC)=O.FC(C(=O)O)(F)F.C1(=CC=CC=C1)OC>>N[C@@H](CCSC)C(=O)OC1CCCN(C2=C1C=C(C=C2)Cl)C(C2=C(C=C(C=C2)NC(C2=C(C=CC=C2)C)=O)OC)=O | CC(C)(C)OC(=O)[NH:30][C@H:29]([C:27]([O:26][CH:25]1[CH2:24][CH2:23][CH2:22][N:21]([C:19]([c:18]2[c:3]([O:2][CH3:1])[cH:4][c:5]([NH:6][C:7](=[O:8])[c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[CH3:15])[cH:16][cH:17]2)=[O:20])[c:41]2[c:35]1[cH:36][c:37]([Cl:38])[cH:39][cH:40]2)=[O:28])[CH2:31][CH2:32][S:33][CH3:34]>>[CH3:1][... | COc1cc(NC(=O)c2ccccc2C)ccc1C(=O)N1CCCC(OC(=O)[C@H](CCSC)NC(=O)OC(C)(C)C)c2cc(Cl)ccc21 | COc1cc(NC(=O)c2ccccc2C)ccc1C(=O)N1CCCC(OC(=O)[C@@H](N)CCSC)c2cc(Cl)ccc21 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C(Nc1ccc(C(=O)N2CCCCc3ccccc32)cc1)c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[C:2](-[C:3])-[NH2;D1;+0:1] | 32.2 | [{"value": 32.2, "product": "N[C@@H](CCSC)C(=O)OC1CCCN(C2=C1C=C(C=C2)Cl)C(C2=C(C=C(C=C2)NC(C2=C(C=CC=C2)C)=O)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A uniform solution of 5-(N-tert-butoxycarbonyl-L-methionyloxy)-7-chloro-1-[2-methoxy-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (1.27 g), trifluoroacetic acid (2.5 ml) and anisole (0.6 ml) is stirred at room temperature for 2 hours. The trifluoroacetic acid is almost distilled off under reduced ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCCC[NH]2 | HO- | null | null | null | COc1cc(NC(=O)c2ccccc2C)ccc1C(=O)N1CCCC(OC(=O)[C@H](CCSC)NC(=O)OC(C)(C)C)c2cc(Cl)ccc21>>COc1cc(NC(=O)c2ccccc2C)ccc1C(=O)N1CCCC(OC(=O)[C@@H](N)CCSC)c2cc(Cl)ccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-95de830301e84a0d9f33eedda961e5bd | CN(C)CC(=O)O.Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCCC(CO)c3cc(Cl)ccc32)cc1>>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCCC(COC(=O)CN(C)C)c3cc(Cl)ccc32)cc1 | C1(CCCCC1)N=C=NC1CCCCC1.CN(C)C1=NC=CC=C1.Cl.CN(C)C1=NC=CC=C1.OCC1CCCN(C2=C1C=C(C=C2)Cl)C(C2=CC=C(C=C2)NC(C2=C(C=CC=C2)C)=O)=O.C(O)([O-])=O.[Na+].Cl.CN(CC(=O)O)C>>Cl.CN(CC(=O)OCC1CCCN(C2=C1C=C(C=C2)Cl)C(C2=CC=C(C=C2)NC(C2=C(C=CC=C2)C)=O)=O)C | O[C:24](=[O:25])[CH2:26][N:27]([CH3:28])[CH3:29].[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[N:17]2[CH2:18][CH2:19][CH2:20][CH:21]([CH2:22][OH:23])[c:30]3[cH:31][c:32]([Cl:33])[cH:34][cH:35][c:36]32)[cH:37][cH:38]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7... | CN(C)CC(=O)O.Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCCC(CO)c3cc(Cl)ccc32)cc1 | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCCC(COC(=O)CN(C)C)c3cc(Cl)ccc32)cc1 | null | null | C(C)(=O)O.C(Cl)(Cl)Cl.CO | Acylation | Esterification of Carboxylic Acids | d9bd78214ee7dbc907e499722ae01849a72d188753963443e5df9fe42c31c43b | 3652e761944e8ef7ee40675a156c8ae39909c72166786934d88652debf2ec1ac | O=C(Nc1ccc(C(=O)N2CCCCc3ccccc32)cc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6]-[C:5] | 141.6 | [{"value": 141.6, "product": "Cl.CN(CC(=O)OCC1CCCN(C2=C1C=C(C=C2)Cl)C(C2=CC=C(C=C2)NC(C2=C(C=CC=C2)C)=O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a solution of 5-hydroxymethyl-7-chloro-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.4 g) in chloroform (10 ml) are dissolved with heating dimethylaminopyridine (0.41 g) and dimethylaminopyridine hydrochloride (0.35 g), and thereto is added N,N-dimethylglycine hydrochloride (0.15 g) at roo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCCC[NH]2 | HO- | C(C)(=O)O.C(Cl)(Cl)Cl.CO | null | null | CN(C)CC(=O)O.Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCCC(CO)c3cc(Cl)ccc32)cc1>C(C)(=O)O.C(Cl)(Cl)Cl.CO>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCCC(COC(=O)CN(C)C)c3cc(Cl)ccc32)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-afa3792d8ff0460690d319722a9ee47e | CCOC(=O)COC1CCCN(C(=O)c2ccc(NC(=O)c3ccccc3C)cc2)c2ccc(Cl)cc21>>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCCC(OCCO)c3cc(Cl)ccc32)cc1 | Cl.C(C)OC(=O)COC1CCCN(C2=C1C=C(C=C2)Cl)C(C2=CC=C(C=C2)NC(C2=C(C=CC=C2)C)=O)=O.[BH4-].[Li+]>>OCCOC1CCCN(C2=C1C=C(C=C2)Cl)C(C2=CC=C(C=C2)NC(C2=C(C=CC=C2)C)=O)=O | CCO[C:24]([CH2:23][O:22][CH:21]1[CH2:20][CH2:19][CH2:18][N:17]([C:15]([c:14]2[cH:13][cH:12][c:11]([NH:10][C:8]([c:7]3[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]3)=[O:9])[cH:34][cH:33]2)=[O:16])[c:32]2[c:26]1[cH:27][c:28]([Cl:29])[cH:30][cH:31]2)=[O:25]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[... | CCOC(=O)COC1CCCN(C(=O)c2ccc(NC(=O)c3ccccc3C)cc2)c2ccc(Cl)cc21 | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCCC(OCCO)c3cc(Cl)ccc32)cc1 | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | O=C(Nc1ccc(C(=O)N2CCCCc3ccccc32)cc1)c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[#8:4]>>[#8:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | 79.1 | [{"value": 79.1, "product": "OCCOC1CCCN(C2=C1C=C(C=C2)Cl)C(C2=CC=C(C=C2)NC(C2=C(C=CC=C2)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-ethoxycarbonylmethoxy-7-chloro-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (2.2 g) in tetrahydrofuran (50 ml) is added with stirring lithium borohydride (0.28 g) at room temperature, and the mixture is refluxed for 30 minutes. The reaction solution is poured into diluted hyd... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCCC[NH]2 | HO- | O1CCCC1 | null | null | CCOC(=O)COC1CCCN(C(=O)c2ccc(NC(=O)c3ccccc3C)cc2)c2ccc(Cl)cc21>O1CCCC1>Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCCC(OCCO)c3cc(Cl)ccc32)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-09459eb81e7b4be98bb3082439814f71 | CN1CCNCC1.COc1cc(NC(=O)c2ccccc2C)ccc1C(=O)N1CCCC(OCCOS(=O)(=O)c2ccc(C)cc2)c2cc(F)ccc21>>COc1cc(NC(=O)c2ccccc2C)ccc1C(=O)N1CCCC(OCCN2CCN(C)CC2)c2cc(F)ccc21 | C1(=CC=C(C=C1)S(=O)(=O)OCCOC1CCCN(C2=C1C=C(C=C2)F)C(C2=C(C=C(C=C2)NC(C2=C(C=CC=C2)C)=O)OC)=O)C.CN1CCNCC1.[I-].[Na+]>>CN1CCN(CC1)CCOC1CCCN(C2=C1C=C(C=C2)F)C(C2=C(C=C(C=C2)NC(C2=C(C=CC=C2)C)=O)OC)=O | [NH:29]1[CH2:30][CH2:31][N:32]([CH3:33])[CH2:34][CH2:35]1.Cc1ccc(S(=O)(=O)O[CH2:28][CH2:27][O:26][CH:25]2[CH2:24][CH2:23][CH2:22][N:21]([C:19]([c:18]3[c:3]([O:2][CH3:1])[cH:4][c:5]([NH:6][C:7](=[O:8])[c:9]4[cH:10][cH:11][cH:12][cH:13][c:14]4[CH3:15])[cH:16][cH:17]3)=[O:20])[c:42]3[c:36]2[cH:37][c:38]([F:39])[cH:40][cH:... | CN1CCNCC1.COc1cc(NC(=O)c2ccccc2C)ccc1C(=O)N1CCCC(OCCOS(=O)(=O)c2ccc(C)cc2)c2cc(F)ccc21 | COc1cc(NC(=O)c2ccccc2C)ccc1C(=O)N1CCCC(OCCN2CCN(C)CC2)c2cc(F)ccc21 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 883f55ad833601fa4f6fc3baadcfd9f1ad53f2d6935818c711f682845b8ecc58 | 71b4ac4449ece5e0df64e56caf0f1cbac76e83f802a92104cfb6c6c861b6a71c | O=C(Nc1ccc(C(=O)N2CCCC(OCCN3CCNCC3)c3ccccc32)cc1)c1ccccc1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[#8:3]):c:c:1.[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | null | [] | null | null | 3 | DAY | 5-[2-(p-Toluenesulfonyloxy)ethoxy]-7-fluoro-1-[2-methoxy-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.4 g), N-methylpiperazine (0.38 ml) and sodium iodide (0.3 g) are dispersed in dimethylformamide (10 ml), and the mixture is stirred at room temperature for 3 days. The reaction mixture is conce... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1 | c1ccccc1.c1ccccc1.C1C[NH]CC[NH]1.c1ccc2c(c1)CCCC[NH]2 | TsOH.HO- | CN(C=O)C | null | 72 | CN1CCNCC1.COc1cc(NC(=O)c2ccccc2C)ccc1C(=O)N1CCCC(OCCOS(=O)(=O)c2ccc(C)cc2)c2cc(F)ccc21>CN(C=O)C>COc1cc(NC(=O)c2ccccc2C)ccc1C(=O)N1CCCC(OCCN2CCN(C)CC2)c2cc(F)ccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-51fadc04c6db458b83e946b701fe0f2a | CC(=O)N1CCNCC1.Cc1ccc(S(=O)(=O)OCCC2CCCN(C(=O)c3ccc(NC(=O)c4ccccc4C)cc3C)c3ccc(Cl)cc32)cc1>>CC(=O)N1CCN(CCC2CCCN(C(=O)c3ccc(NC(=O)c4ccccc4C)cc3C)c3ccc(Cl)cc32)CC1 | Cl.C1(=CC=C(C=C1)S(=O)(=O)OCCC1CCCN(C2=C1C=C(C=C2)Cl)C(C2=C(C=C(C=C2)NC(C2=C(C=CC=C2)C)=O)C)=O)C.[I-].[Na+].C(C)(=O)N1CCNCC1>>Cl.C(C)(=O)N1CCN(CC1)CCC1CCCN(C2=C1C=C(C=C2)Cl)C(C2=C(C=C(C=C2)NC(C2=C(C=CC=C2)C)=O)C)=O | [CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][NH:7][CH2:41][CH2:42]1.Cc1ccc(S(=O)(=O)O[CH2:8][CH2:9][CH:10]2[CH2:11][CH2:12][CH2:13][N:14]([C:15](=[O:16])[c:17]3[cH:18][cH:19][c:20]([NH:21][C:22](=[O:23])[c:24]4[cH:25][cH:26][cH:27][cH:28][c:29]4[CH3:30])[cH:31][c:32]3[CH3:33])[c:34]3[cH:35][cH:36][c:37]([Cl:38])[cH:39][c:4... | CC(=O)N1CCNCC1.Cc1ccc(S(=O)(=O)OCCC2CCCN(C(=O)c3ccc(NC(=O)c4ccccc4C)cc3C)c3ccc(Cl)cc32)cc1 | CC(=O)N1CCN(CCC2CCCN(C(=O)c3ccc(NC(=O)c4ccccc4C)cc3C)c3ccc(Cl)cc32)CC1 | null | null | CN(C=O)C.C(C)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 9d271698b0c48162ad18ec9c479844bc505434e9294038bc9af6d1140123fb4f | 71b4ac4449ece5e0df64e56caf0f1cbac76e83f802a92104cfb6c6c861b6a71c | O=C(Nc1ccc(C(=O)N2CCCC(CCN3CCNCC3)c3ccccc32)cc1)c1ccccc1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[C:3]):c:c:1.[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 121.5 | [{"value": 121.5, "product": "Cl.C(C)(=O)N1CCN(CC1)CCC1CCCN(C2=C1C=C(C=C2)Cl)C(C2=C(C=C(C=C2)NC(C2=C(C=CC=C2)C)=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 5-[2-(p-toluenesulfonyloxy)ethyl]-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.25 g) in dry dimethylformamide (20 ml) are added sodium iodide (0.178 g) and 4-acetylpiperazine (0.152 g), and the mixture is stirred at room temperature for one hour. The mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1ccccc1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1.c1ccc2c(c1)CCCC[NH]2 | TsOH.HO- | CN(C=O)C.C(C)OCC | null | 1 | CC(=O)N1CCNCC1.Cc1ccc(S(=O)(=O)OCCC2CCCN(C(=O)c3ccc(NC(=O)c4ccccc4C)cc3C)c3ccc(Cl)cc32)cc1>CN(C=O)C.C(C)OCC>CC(=O)N1CCN(CCC2CCCN(C(=O)c3ccc(NC(=O)c4ccccc4C)cc3C)c3ccc(Cl)cc32)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f062401e98454d87bfd0d4d5cf3629c0 | C=C(C)C(=O)OCC(O)CCl.ClCC1CO1>>C=C(C)C(=O)OCC1CO1.[Cl-] | C(C(=C)C)(=O)OCC(CCl)O.[OH-].[Na+].[OH-].[K+].C(Cl)C1CO1.[OH-].[K+].C(C(=C)C)(=O)OCC(CCl)O>>C(C(=C)C)(=O)OCC1CO1.[Cl-].[K+] | OC(CCl)C[O:6][C:4]([C:2](=[CH2:1])[CH3:3])=[O:5].[CH2:7]([CH:8]1[CH2:9][O:10]1)[Cl:11]>>[CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][CH2:7][CH:8]1[CH2:9][O:10]1.[Cl-:11] | C=C(C)C(=O)OCC(O)CCl.ClCC1CO1 | C=C(C)C(=O)OCC1CO1.[Cl-] | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 32c99f0eb08f47b81bb647b50a09f600dfa27c1940971aad8c430600820adde6 | 94555e253b0dd09ee7a50d5bf9af8bd561b2f56eac7bb8692ecea93d4f41b3cc | C1CO1 | Cl-C-C(-O)-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](=[C;D1;H2:5])-[C;D1;H3:6].[Cl;H0;D1;+0:7]-[CH2;D2;+0:8]-[C:9]1-[#8:10]-[C:11]-1>>[C;D1;H2:5]=[C:4](-[C;D1;H3:6])-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:1]-[CH2;D2;+0:8]-[C:9]1-[#8:10]-[C:11]-1.[Cl-;H0;D0:7] | null | [] | null | null | null | null | A feed with 3-chloro-2-hydroxypropyl methacrylate (CHPMA), epichlorohydrln, and minor amounts of by-products (GMA and heavies such as polymer by-product materials) flows into an epoxidation reactor to which aqueous alkali metal hydroxides such as sodium hydroxide (NaOH) or potassium hydroxide (KOH) and additional epich... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Ester.Secondary alcohol | Ester | null | null | C1CO1 | HCl | O | null | null | C=C(C)C(=O)OCC(O)CCl.ClCC1CO1>O>C=C(C)C(=O)OCC1CO1.[Cl-] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6e955e2991c44b43badb9a9ccdf6b729 | ClCc1ccccc1.c1ccc2[nH]ccc2c1>>c1ccc(Cn2ccc3ccccc32)cc1 | N.C(C1=CC=CC=C1)Cl.[NH2-].[Na+].[Na].N.N1C=CC2=CC=CC=C12>>C(C1=CC=CC=C1)N1C=CC2=CC=CC=C12 | Cl[CH2:5][c:4]1[cH:3][cH:2][cH:1][cH:16][cH:15]1.[nH:6]1[cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][n:6]2[cH:7][cH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]23)[cH:15][cH:16]1 | ClCc1ccccc1.c1ccc2[nH]ccc2c1 | c1ccc(Cn2ccc3ccccc32)cc1 | null | null | CCOCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 92cc004fc3e2a92f5c9aa0385cdf93f1126e35d5aa485f4f5fe9240c9543c8fe | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2ccc3ccccc32)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[c:5]:[c:6]1:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[c:5]:[c:6]1:[c:7]:[c:8]:[c:9]:[n;H0;D3;+0:10]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 30 | MINUTE | To a stirred mixture of sodium amide (prepared from 19.6 g, 0.85 mole of sodium and a few mg of Fe(NO3)3 -9H2O) and 800 mL of liquid NH3 (a dry ice condenser was used) was added a solution of 100 g (0.85 mole) of indole in 250 mL of dry ether during 15 minutes. The mixture was stirred for 30 minutes and then a solution... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | HCl | CCOCC | null | 0.5 | ClCc1ccccc1.c1ccc2[nH]ccc2c1>CCOCC>c1ccc(Cn2ccc3ccccc32)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0aa88ee7cb854783bfc493ea25668c80 | ClCc1ccc(Cl)cc1.c1ccc2[nH]ccc2c1>>Clc1ccc(Cn2ccc3ccccc32)cc1 | N1C=CC2=CC=CC=C12.ClC1=CC=C(CCl)C=C1.[OH-].[K+]>>ClC1=CC=C(CN2C=CC3=CC=CC=C23)C=C1 | Cl[CH2:6][c:5]1[cH:4][cH:3][c:2]([Cl:1])[cH:17][cH:16]1.[nH:7]1[cH:8][cH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]12>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][n:7]2[cH:8][cH:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]23)[cH:16][cH:17]1 | ClCc1ccc(Cl)cc1.c1ccc2[nH]ccc2c1 | Clc1ccc(Cn2ccc3ccccc32)cc1 | null | null | C1(=CC=CC=C1)C.O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 92cc004fc3e2a92f5c9aa0385cdf93f1126e35d5aa485f4f5fe9240c9543c8fe | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2ccc3ccccc32)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[c:5]:[c:6]1:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[c:5]:[c:6]1:[c:7]:[c:8]:[c:9]:[n;H0;D3;+0:10]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 84.1 | [{"value": 84.0, "product": "ClC1=CC=C(CN2C=CC3=CC=CC=C23)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.1, "product": "ClC1=CC=C(CN2C=CC3=CC=CC=C23)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 11.72 g (0.1 mole) of indole, 17.71 g (0.11 mole) of 4-chlorobenzyl chloride, 33 g (0.5 mole) of 85% KOH, 14 mL of H2O, 2.5 g (2.5 mmoles) of PEG-1000 and 100 mL of toluene was stirred and heated at 55°-65° for 22 hours. After cooling to room temperature, 50 mL of H2O was added. The layers were separated. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | HCl | C1(=CC=CC=C1)C.O | null | null | ClCc1ccc(Cl)cc1.c1ccc2[nH]ccc2c1>C1(=CC=CC=C1)C.O>Clc1ccc(Cn2ccc3ccccc32)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9e54ac87e6cd4333953c4b9787bd6f06 | Brc1ccccc1.c1ccc2[nH]ccc2c1>>c1ccc(-n2ccc3ccccc32)cc1 | N1C=CC2=CC=CC=C12.BrC1=CC=CC=C1.C([O-])([O-])=O.[K+].[K+].CN(C)C=O>>C1(=CC=CC=C1)N1C=CC2=CC=CC=C12 | Br[c:4]1[cH:3][cH:2][cH:1][cH:15][cH:14]1.[nH:5]1[cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12>>[cH:1]1[cH:2][cH:3][c:4](-[n:5]2[cH:6][cH:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]23)[cH:14][cH:15]1 | Brc1ccccc1.c1ccc2[nH]ccc2c1 | c1ccc(-n2ccc3ccccc32)cc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 85a6484ae5d3889901774194dcc76ef1462fff5cf0c72d425fcc6d34b5fde5ee | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(-n2ccc3ccccc32)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[c:6]:[c:7]1:[c:8]:[c:9]:[c:10]:[nH;D2;+0:11]:1>>[c:6]:[c:7]1:[c:8]:[c:9]:[c:10]:[n;H0;D3;+0:11]:1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 20.2 | [{"value": 20.0, "product": "C1(=CC=CC=C1)N1C=CC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 20.2, "product": "C1(=CC=CC=C1)N1C=CC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 17.57 g (0.15 mole) of indole, 23.55 g (0.15 mole) of bromobenzene, 21 g of anhydrous potassium carbonate, 0.75 g of CuO, and 30 mL of DMF was stirred and heated under reflux for 43 hours. The cooled mixture was diluted with 200 mL of H2O and extracted with 150 mL of ether. The extract was washed with H2O ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | HBr | O | null | null | Brc1ccccc1.c1ccc2[nH]ccc2c1>O>c1ccc(-n2ccc3ccccc32)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3ef121dbf1f0400b85825dd9302cc9ce | ClCc1ccccc1.c1ccc(-c2cc3ccccc3[nH]2)cc1>>c1ccc(Cn2c(-c3ccccc3)cc3ccccc32)cc1 | C1(=CC=CC=C1)C=1NC2=CC=CC=C2C1.C(C1=CC=CC=C1)Cl.[OH-].[K+]>>C(C1=CC=CC=C1)N1C(=CC2=CC=CC=C12)C1=CC=CC=C1 | Cl[CH2:5][c:4]1[cH:3][cH:2][cH:1][cH:22][cH:21]1.[nH:6]1[c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]12>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][n:6]2[c:7](-[c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)[cH:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]23)[cH:21][cH:22]1 | ClCc1ccccc1.c1ccc(-c2cc3ccccc3[nH]2)cc1 | c1ccc(Cn2c(-c3ccccc3)cc3ccccc32)cc1 | null | null | C1(=CC=CC=C1)C.O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 16b46a8af20339f7ff0b611b4ac5dd01fe35ba577361e893c359dfa478dc1974 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2c(-c3ccccc3)cc3ccccc32)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[c:5]:[c:6]1:[c:7]:[c:8]:[c:9](-[c:10]):[nH;D2;+0:11]:1>>[c:5]:[c:6]1:[c:7]:[c:8]:[c:9](-[c:10]):[n;H0;D3;+0:11]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 13.2 | [{"value": 13.0, "product": "C(C1=CC=CC=C1)N1C(=CC2=CC=CC=C12)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 13.2, "product": "C(C1=CC=CC=C1)N1C(=CC2=CC=CC=C12)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 19.33 g (0.1 mole) of 2-phenylindole, 13.92 g (0.11 mole) of benzyl chloride, 33 g (0.5 mole) of 85% KOH, 14 mL of H2O, 2.5 g (2.5 mmoles) of PEG-1000, and 100 mL of toluene was stirred and heated at 55°-60° for 24 hours. After cooling to room temperature, 100 mL of H2O was added. The layers were separated... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1cc2ccccc2[nH]1 | c1ccccc1.c1ccccc1.c1cc2ccccc2[nH]1 | HCl | C1(=CC=CC=C1)C.O | null | null | ClCc1ccccc1.c1ccc(-c2cc3ccccc3[nH]2)cc1>C1(=CC=CC=C1)C.O>c1ccc(Cn2c(-c3ccccc3)cc3ccccc32)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0121012381ad40bb9bdeb58d7a76e8eb | BrCc1ccccc1.Clc1ccc2[nH]ccc2c1>>Clc1ccc2c(ccn2Cc2ccccc2)c1 | ClC=1C=C2C=CNC2=CC1.C(C1=CC=CC=C1)Br.C1COCCOCCOCCOCCOCCO1.CC(C)([O-])C.[K+]>>C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)Cl | Br[CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.[Cl:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7][cH:8][nH:9]2)[cH:17]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7][cH:8][n:9]2[CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17]1 | BrCc1ccccc1.Clc1ccc2[nH]ccc2c1 | Clc1ccc2c(ccn2Cc2ccccc2)c1 | null | null | CCOCC.O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 92cc004fc3e2a92f5c9aa0385cdf93f1126e35d5aa485f4f5fe9240c9543c8fe | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2ccc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[c:5]:[c:6]1:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[c:6]:1:[c:5]):[c:4] | 90 | [{"value": 90.0, "product": "C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.6, "product": "C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | To a solution of 0.8 g (3.03 mmoles) of 18-crown-6 in 100 mL of dry ether was added 4.39 g (39.12 mmoles) potassium tert-butoxide. The mixture was stirred while 5.08 g (33.51 mmoles) of 5-chloroindole was added. The stirring was continued for 0.5 hour. Most of the solid dissolved. Then 6.69 g (39.11 mmoles) of benzyl b... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HBr | CCOCC.O | null | 0.5 | BrCc1ccccc1.Clc1ccc2[nH]ccc2c1>CCOCC.O>Clc1ccc2c(ccn2Cc2ccccc2)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1e9c28188ba44ba1b3e90f556b1d3cd8 | Cc1cc2ccccc2[nH]1.ClCc1ccccc1>>Cc1cc2ccccc2n1Cc1ccccc1 | CC=1NC2=CC=CC=C2C1.C(C1=CC=CC=C1)Cl.[OH-].[K+]>>C(C1=CC=CC=C1)N1C(=CC2=CC=CC=C12)C | [CH3:1][c:2]1[cH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[nH:10]1.Cl[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][c:2]1[cH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[n:10]1[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | Cc1cc2ccccc2[nH]1.ClCc1ccccc1 | Cc1cc2ccccc2n1Cc1ccccc1 | null | null | C1(=CC=CC=C1)C.O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 16b46a8af20339f7ff0b611b4ac5dd01fe35ba577361e893c359dfa478dc1974 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2ccc3ccccc32)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[c:6]1:[c:7]:[c:8]:[c:9](:[c:10]):[nH;D2;+0:11]:1>>[C;D1;H3:5]-[c:6]1:[c:7]:[c:8]:[c:9](:[c:10]):[n;H0;D3;+0:11]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 9.4 | [{"value": 9.0, "product": "C(C1=CC=CC=C1)N1C(=CC2=CC=CC=C12)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 9.4, "product": "C(C1=CC=CC=C1)N1C(=CC2=CC=CC=C12)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 13.11 g (0.1 mole) of 2-methylindole, 13.92 g (0.11 mole) of benzyl chloride, 33 g (0.5 mole) of 85% KOH, 14 mL of H2O, 2.5 g (2.5 mmoles) of PEG-1000, and 100 mL of toluene was stirred and heated at 60° for 23 hours. After cooling to room temperature, 100 mL of H2O was added. The layers were separated. Th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1cc2ccccc2[nH]1 | c1cc2ccccc2[nH]1.c1ccccc1 | HCl | C1(=CC=CC=C1)C.O | null | null | Cc1cc2ccccc2[nH]1.ClCc1ccccc1>C1(=CC=CC=C1)C.O>Cc1cc2ccccc2n1Cc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b299b94d41124dd7b4f6bdbadde51879 | Cc1cc2ccccc2[nH]1.ClCc1ccccc1>>Cc1cc2ccccc2n1Cc1ccccc1 | CC=1NC2=CC=CC=C2C1.C(C1=CC=CC=C1)Cl.C1COCCOCCOCCOCCOCCO1.CC(C)([O-])C.[K+]>>C(C1=CC=CC=C1)N1C(=CC2=CC=CC=C12)C | [CH3:1][c:2]1[cH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[nH:10]1.Cl[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][c:2]1[cH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[n:10]1[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | Cc1cc2ccccc2[nH]1.ClCc1ccccc1 | Cc1cc2ccccc2n1Cc1ccccc1 | null | null | CCOCC.O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 16b46a8af20339f7ff0b611b4ac5dd01fe35ba577361e893c359dfa478dc1974 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2ccc3ccccc32)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[c:6]1:[c:7]:[c:8]:[c:9](:[c:10]):[nH;D2;+0:11]:1>>[C;D1;H3:5]-[c:6]1:[c:7]:[c:8]:[c:9](:[c:10]):[n;H0;D3;+0:11]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 0.5 | HOUR | To a solution of 2.39 g (9.04 mmoles) of 18-crown-6 in 250 mL of dry ether was added 13.1 g (116.7 mmoles) of potassium tert-butoxide. The mixture was stirred while 13.11 g (100 mmoles) of 2-methylindole was added. The stirring was continued for 0.5 hour. Most of the solid dissolved. Then 20 g (116.9 mmoles) of benzyl ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1cc2ccccc2[nH]1 | c1cc2ccccc2[nH]1.c1ccccc1 | HCl | CCOCC.O | null | 0.5 | Cc1cc2ccccc2[nH]1.ClCc1ccccc1>CCOCC.O>Cc1cc2ccccc2n1Cc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a27889ee44e040db9dcdb94b80457c09 | C=CCBr.c1ccc2[nH]ccc2c1>>C=CCn1ccc2ccccc21 | N1C=CC2=CC=CC=C12.C(C=C)Br.C1COCCOCCOCCOCCOCCO1.CC(C)([O-])C.[K+]>>C(C=C)N1C=CC2=CC=CC=C12 | Br[CH2:3][CH:2]=[CH2:1].[nH:4]1[cH:5][cH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12>>[CH2:1]=[CH:2][CH2:3][n:4]1[cH:5][cH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12 | C=CCBr.c1ccc2[nH]ccc2c1 | C=CCn1ccc2ccccc21 | null | null | CCOCC.O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2090660879279eaab8ecde544313a56fd80d46bfd3ea06a7bc9e63018902ce70 | 4c606dc54eac846ef90c7b3255999ceff93277747e7c2b0ddd37ccf25562b7c5 | c1ccc2[nH]ccc2c1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[c:4]:[c:5]1:[c:6]:[c:7]:[c:8]:[nH;D2;+0:9]:1>>[C;D1;H2:3]=[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[c:8]:[c:7]:[c:6]:[c:5]:1:[c:4] | 74 | [{"value": 74.0, "product": "C(C=C)N1C=CC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.8, "product": "C(C=C)N1C=CC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 2.39 g (9.04 mmoles) of 18-crown-6 in 250 ml of dry ether was added 13.1 g (116.7 mmoles) of potassium tert-butoxide. The mixture was stirred while 11.72 g (100 mmoles) indole was added. The stirring was continued for 3 hours. All of the solid did not dissolve. Then 14.1 g (116.5 mmoles) of allyl bromi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Allyl | Allyl | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HBr | CCOCC.O | null | 3 | C=CCBr.c1ccc2[nH]ccc2c1>CCOCC.O>C=CCn1ccc2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d138d27f7a2240c7b892e2313bc78ca3 | Cc1ccc2[nH]ccc2c1.ClCc1ccccc1>>Cc1ccc2c(ccn2Cc2ccccc2)c1 | [NH2-].[Na+].N.C(C1=CC=CC=C1)Cl.CC=1C=C2C=CNC2=CC1.N>>C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7][cH:8][nH:9]2)[cH:17]1.Cl[CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7][cH:8][n:9]2[CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17]1 | Cc1ccc2[nH]ccc2c1.ClCc1ccccc1 | Cc1ccc2c(ccn2Cc2ccccc2)c1 | null | null | CCOCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 92cc004fc3e2a92f5c9aa0385cdf93f1126e35d5aa485f4f5fe9240c9543c8fe | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2ccc3ccccc32)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[c:5]:[c:6]1:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[c:6]:1:[c:5]):[c:4] | 53 | [{"value": 53.0, "product": "C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.7, "product": "C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To a stirred mixture of sodium amide (prepared from 0.9 g 39.13 mmoles of sodium) and ca 100 ml of liquid ammonia was added a solution of 5.08 g (38.73 mmoles) of 5-methylindole in 100 ml of ether during 5 minutes. The mixture was stirred for 1.5 hours. Then a solution of 5.15 g (40.68 mmoles) of benzyl chloride in 100... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HCl | CCOCC | null | 1.5 | Cc1ccc2[nH]ccc2c1.ClCc1ccccc1>CCOCC>Cc1ccc2c(ccn2Cc2ccccc2)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d0c9152d9e564c87bc2c916dccd31853 | ClCc1ccccc1.Fc1ccc2[nH]ccc2c1>>Fc1ccc2c(ccn2Cc2ccccc2)c1 | C(C1=CC=CC=C1)Cl.FC=1C=C2C=CNC2=CC1.C1COCCOCCOCCOCCOCCO1.CC(C)([O-])C.[K+]>>C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)F | Cl[CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7][cH:8][nH:9]2)[cH:17]1>>[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7][cH:8][n:9]2[CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17]1 | ClCc1ccccc1.Fc1ccc2[nH]ccc2c1 | Fc1ccc2c(ccn2Cc2ccccc2)c1 | null | null | CCOCC.O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 92cc004fc3e2a92f5c9aa0385cdf93f1126e35d5aa485f4f5fe9240c9543c8fe | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2ccc3ccccc32)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[c:5]:[c:6]1:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[c:6]:1:[c:5]):[c:4] | 14.1 | [{"value": 14.0, "product": "C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 14.1, "product": "C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | To a solution of 0.8 g (3.03 mmoles) of 18-crown-6 in 100 ml of dry ether was added 3.27 g (29.14 mmoles) of potassium tert-butoxide. The mixture was stirred while a solution of 3.75 g (27.75 mmoles) of 5-fluoroindole in 80 ml of ether was added. The stirring was continued for 0.5 hour. Solid was present. Then 3.69 g (... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HCl | CCOCC.O | null | 0.5 | ClCc1ccccc1.Fc1ccc2[nH]ccc2c1>CCOCC.O>Fc1ccc2c(ccn2Cc2ccccc2)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a2f03c228cfc4a80915bffdae99800be | CCOC(=O)C(OCC)OCC.[NH4+]>>CCOC(OCC)C(N)=O | C(C)OC(C(=O)OCC)OCC.[OH-].[NH4+]>>C(C)OC(C(=O)N)OCC | CCO[C:8]([CH:4]([O:3][CH2:2][CH3:1])[O:5][CH2:6][CH3:7])=[O:10].[NH4+:9]>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[C:8]([NH2:9])=[O:10] | CCOC(=O)C(OCC)OCC.[NH4+] | CCOC(OCC)C(N)=O | null | null | C(Cl)Cl | Acylation | OtherReaction | d5b10d4f469e7a196a3b04a6a9e159a7d90514b6df5b50c1197d4b1b774c04e1 | adc0ef6f6c1340dd2dbab737c85bf17fc842769181c5db1a2b4f82b391b28f9f | null | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[#8:4])-[#8:5].[NH4+;D0:6]>>[#8:4]-[C:3](-[#8:5])-[C;H0;D3;+0:1](-[NH2;D1;+0:6])=[O;D1;H0:2] | 87 | [{"value": 87.0, "product": "C(C)OC(C(=O)N)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A mixture of 24.85 g of ethyl diethoxyacetate and 140 ml of concentrated ammonium hydroxide was stirred for 3 hours. The ammonia and H2O were evaporated under reduced pressure on a water bath at 50°-60° leaving a wet solid. The wet solid was dried in a vacuum oven at 53° for 18 hours giving a dark pink solid. The solid... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary amide | null | null | null | HO- | C(Cl)Cl | null | 3 | CCOC(=O)C(OCC)OCC.[NH4+]>C(Cl)Cl>CCOC(OCC)C(N)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1e607e457e3c44ccb98525fa715b1116 | CO.O=C(O)Cc1cccc(C(F)(F)F)c1>>COC(=O)Cc1cccc(C(F)(F)F)c1 | FC(C=1C=C(C=CC1)CC(=O)O)(F)F.CO>>COC(CC1=CC(=CC=C1)C(F)(F)F)=O | [CH3:1][OH:2].O[C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1 | CO.O=C(O)Cc1cccc(C(F)(F)F)c1 | COC(=O)Cc1cccc(C(F)(F)F)c1 | null | null | CCOC(=O)C | 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] | 89 | [{"value": 89.0, "product": "COC(CC1=CC(=CC=C1)C(F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Into a solution of 3-trifluoromethylphenylacetic acid (20.0 g. 98 mmol) in MeOH (100 mL), cooled in an ice-water bath, was bubbled HCl (g) for 15 min. The mixture was allowed to warm to room temperature and was then concentrated in vacuo to furnish a clear, yellow-green liquid which was diluted with EtOAc (0.25L) and w... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | CCOC(=O)C | null | null | CO.O=C(O)Cc1cccc(C(F)(F)F)c1>CCOC(=O)C>COC(=O)Cc1cccc(C(F)(F)F)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-117b19d4882f4413bce8c78046c64c8c | O=C(O)C(NCc1cccc(C(F)(F)F)c1)c1cn(Cc2ccccc2)c2ccccc12>>O=C([O-])C(NCc1cccc(C(F)(F)F)c1)c1cn(Cc2ccccc2)c2ccccc12 | FC(C=1C=C(CNC(C(=O)O)C2=CN(C3=CC=CC=C23)CC2=CC=CC=C2)C=CC1)(F)F.[OH-].[Na+]>>FC(C=1C=C(CNC(C(=O)[O-])C2=CN(C3=CC=CC=C23)CC2=CC=CC=C2)C=CC1)(F)F.[Na+] | [O:1]=[C:2]([OH:3])[CH:4]([NH:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16]1)[c:17]1[cH:18][n:19]([CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[c:27]2[cH:28][cH:29][cH:30][cH:31][c:32]12>>[O:1]=[C:2]([O-:3])[CH:4]([NH:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]([C:12]([F:13])([F:14])... | O=C(O)C(NCc1cccc(C(F)(F)F)c1)c1cn(Cc2ccccc2)c2ccccc12 | O=C([O-])C(NCc1cccc(C(F)(F)F)c1)c1cn(Cc2ccccc2)c2ccccc12 | null | null | CO | Oxidation | Carboxylic acid to carboxylate | af9382a4a3fca177895c8a400271aa22025197fc08b983f9d71150044c1e6777 | b3097057beeca787f1d4960a7ee432572ee7aecad541233195b0dbbc0f674e9c | c1ccc(CNCc2cn(Cc3ccccc3)c3ccccc23)cc1 | [C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4]>>[C:1]-[C:2](-[O-;H0;D1:4])=[O;D1;H0:3] | 86 | [{"value": 86.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3 g (6.84 mmoles) of α-[3-(trifluoromethyl)benzylamino]-1-benzylindole 3-acetic acid, 3.4 ml (6.80 mmoles) of 2N NaOH, and 100 ml of MeOH was warmed until a solution was obtained (one to two hours). The solvent was evaporated. The residue was dried in a vacuum oven at 66° for 70 hours giving 2.70 (86%) of ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | c1ccccc1.c1ccccc1.c1c[nH]c2ccccc12 | null | CO | null | null | O=C(O)C(NCc1cccc(C(F)(F)F)c1)c1cn(Cc2ccccc2)c2ccccc12>CO>O=C([O-])C(NCc1cccc(C(F)(F)F)c1)c1cn(Cc2ccccc2)c2ccccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5e05af3e4327470e88c75d53a7f6a7c7 | CCI.O=C(O)C(NCc1cccc(C(F)(F)F)c1)c1cn(Cc2ccccc2)c2ccccc12>>CCOC(=O)C(NCc1cccc(C(F)(F)F)c1)c1cn(Cc2ccccc2)c2ccccc12 | CN(C=O)C.FC(C=1C=C(CNC(C(=O)O)C2=CN(C3=CC=CC=C23)CC2=CC=CC=C2)C=CC1)(F)F.C[O-].[Na+].C(C)I>>FC(C=1C=C(CNC(C(=O)OCC)C2=CN(C3=CC=CC=C23)CC2=CC=CC=C2)C=CC1)(F)F | I[CH2:2][CH3:1].[OH:3][C:4](=[O:5])[CH:6]([NH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18]1)[c:19]1[cH:20][n:21]([CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[c:29]2[cH:30][cH:31][cH:32][cH:33][c:34]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][CH2:8][c:9]1[cH:10][cH:11][cH... | CCI.O=C(O)C(NCc1cccc(C(F)(F)F)c1)c1cn(Cc2ccccc2)c2ccccc12 | CCOC(=O)C(NCc1cccc(C(F)(F)F)c1)c1cn(Cc2ccccc2)c2ccccc12 | null | null | [Cl-].[Na+].O.CO.CCOCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | c1ccc(CNCc2cn(Cc3ccccc3)c3ccccc23)cc1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[C:3]-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6]>>[C:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[C;D1;H3:2] | null | [] | null | null | 2 | HOUR | To a magnetically stirred suspension of α-[3-(trifluoromethyl)benzylamino)-1-benzylindole-3-acetic acid (21.9 g, 0.05 mol) in 250 mL of methanol at room temperature was treated with 11.34 g of sodium methoxide (25% in methanol) at once. The resulting solution was stirred for two hours, concentrated directly on a rotary... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | c1ccccc1.c1ccccc1.c1c[nH]c2ccccc12 | HI | [Cl-].[Na+].O.CO.CCOCC | null | 2 | CCI.O=C(O)C(NCc1cccc(C(F)(F)F)c1)c1cn(Cc2ccccc2)c2ccccc12>[Cl-].[Na+].O.CO.CCOCC>CCOC(=O)C(NCc1cccc(C(F)(F)F)c1)c1cn(Cc2ccccc2)c2ccccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-37e9705164da464eb5088a85a9aeda49 | CCOC(=O)C(NCc1cccc(C(F)(F)F)c1)c1c[nH]c2ccccc12.CCOC(=O)Cl>>CCOC(=O)C(NCc1cccc(C(F)(F)F)c1)c1cn(C(=O)OCC)c2ccccc12.Cl | ClC(=O)OCC.FC(C=1C=C(CNC(C(=O)OCC)C2=CNC3=CC=CC=C23)C=CC1)(F)F.[H-].[Na+]>>Cl.FC(C=1C=C(CNC(C(=O)OCC)C2=CN(C3=CC=CC=C23)C(=O)OCC)C=CC1)(F)F | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18]1)[c:19]1[cH:20][nH:21][c:27]2[cH:28][cH:29][cH:30][cH:31][c:32]12.[C:22](=[O:23])([O:24][CH2:25][CH3:26])[Cl:33]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][c:1... | CCOC(=O)C(NCc1cccc(C(F)(F)F)c1)c1c[nH]c2ccccc12.CCOC(=O)Cl | CCOC(=O)C(NCc1cccc(C(F)(F)F)c1)c1cn(C(=O)OCC)c2ccccc12.Cl | null | null | CN(C)C=O | Acylation | N-alkylation of secondary amines with alkyl halides | 33124901c27cb4c2fff33775c779f3741fa39355cb89bbb8a4cc6f24b1c52834 | d03c43b1eb3e007d0a26c663cd0f6b51f594c27d1ade9616fb1640d35a60bddb | c1ccc(CNCc2c[nH]c3ccccc23)cc1 | [C:1]-[#8:2]-[C;H0;D3;+0:3](-[Cl;H0;D1;+0:4])=[O;D1;H0:5].[c:6]:[c:7]1:[c:8]:[c:9]:[c:10]:[nH;D2;+0:11]:1>>[C:1]-[#8:2]-[C;H0;D3;+0:3](=[O;D1;H0:5])-[n;H0;D3;+0:11]1:[c:10]:[c:9]:[c:8]:[c:7]:1:[c:6].[ClH;D0;+0:4] | 66.4 | [{"value": 66.4, "product": "Cl.FC(C=1C=C(CNC(C(=O)OCC)C2=CN(C3=CC=CC=C23)C(=O)OCC)C=CC1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a magnetically stirred solution of ethyl α-[3(trifluoromethyl)-benzylamino]-indole-3-acetate (1.00 g, 2.66 mmol) in 15 mL of DMF was added under nitrogen 0.112 g (2.79 mmol) of sodium hydride (60% oil dispersion). After stirring at room temperature for 10 minutes, 0.26 ml (2.79 mmol) of ethyl chloroformate was added... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether | Ether | c1ccc2[nH]ccc2c1 | c1c[nH]c2ccccc12 | c1ccccc1.c1c[nH]c2ccccc12 | null | CN(C)C=O | null | 0.166667 | CCOC(=O)C(NCc1cccc(C(F)(F)F)c1)c1c[nH]c2ccccc12.CCOC(=O)Cl>CN(C)C=O>CCOC(=O)C(NCc1cccc(C(F)(F)F)c1)c1cn(C(=O)OCC)c2ccccc12.Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f5076b126f9c44638f9cffe98c7e0417 | CC(=O)Cl.O=C(O)C(NCc1cccc(C(F)(F)F)c1)c1cn(Cc2ccccc2)c2ccccc12>>COC(=O)C(NCc1cccc(C(F)(F)F)c1)c1cn(Cc2ccccc2)c2ccccc12 | C(C)(=O)Cl.FC(C=1C=C(CNC(C(=O)O)C2=CN(C3=CC=CC=C23)CC2=CC=CC=C2)C=CC1)(F)F.C(=O)(O)[O-].[Na+].C(=O)(O)[O-].[Na+].Cl>>FC(C=1C=C(CNC(C(=O)OC)C2=CN(C3=CC=CC=C23)CC2=CC=CC=C2)C=CC1)(F)F | O=C(Cl)[CH3:1].[OH:2][C:3](=[O:4])[CH:5]([NH:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17]1)[c:18]1[cH:19][n:20]([CH2:21][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]12>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([NH:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]... | CC(=O)Cl.O=C(O)C(NCc1cccc(C(F)(F)F)c1)c1cn(Cc2ccccc2)c2ccccc12 | COC(=O)C(NCc1cccc(C(F)(F)F)c1)c1cn(Cc2ccccc2)c2ccccc12 | null | null | CO | Heteroatom Alkylation and Arylation | O-methylation | e4e418517831e68b0ae6eff0e20954e6373d72ef6db8a62429d10c826be6ea2e | b1bbfb03e48869c16300667505b58de6f6c5a435aa2a615a319deee7cf33326a | c1ccc(CNCc2cn(Cc3ccccc3)c3ccccc23)cc1 | Cl-C(=O)-[CH3;D1;+0:1].[C:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]>>[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[CH3;D1;+0:1] | null | [] | null | null | 45 | MINUTE | To a magnetically stirred solution of 100 ml of methanol cooled in an ice-acetone bath at ca. -15° C., was treated dropwise with acetyl chloride (27.3 g, 350 mmol, 35 eq) over a six-minute period as a convenient way to generate HCl in situ. The solution was stirred at ambient temperature for 45 minutes, then solid α-[3... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carboxylic acid | Ester | null | null | c1ccccc1.c1ccccc1.c1c[nH]c2ccccc12 | HCl | CO | null | 0.75 | CC(=O)Cl.O=C(O)C(NCc1cccc(C(F)(F)F)c1)c1cn(Cc2ccccc2)c2ccccc12>CO>COC(=O)C(NCc1cccc(C(F)(F)F)c1)c1cn(Cc2ccccc2)c2ccccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9d6b4639e61f428789f790c938140d8e | COC(=O)C(NCc1cccc(C(F)(F)F)c1)c1cn(Cc2ccccc2)c2ccccc12>>CCOC(=O)C(NCc1cccc(C(F)(F)F)c1)c1cn(Cc2ccccc2)c2ccccc12 | Cl.FC(C=1C=C(CNC(C(=O)OC)C2=CN(C3=CC=CC=C23)CC2=CC=CC=C2)C=CC1)(F)F.C[O-].[Na+]>>FC(C=1C=C(CNC(C(=O)OCC)C2=CN(C3=CC=CC=C23)CC2=CC=CC=C2)C=CC1)(F)F | [CH3:2][O:3][C:4](=[O:5])[CH:6]([NH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18]1)[c:19]1[cH:20][n:21]([CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[c:29]2[cH:30][cH:31][cH:32][cH:33][c:34]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]... | COC(=O)C(NCc1cccc(C(F)(F)F)c1)c1cn(Cc2ccccc2)c2ccccc12 | CCOC(=O)C(NCc1cccc(C(F)(F)F)c1)c1cn(Cc2ccccc2)c2ccccc12 | null | null | C(C)O.CO | Miscellaneous | Methylation | 797948efc8975454230354c6926ef43459a60311d668503c7a6b6bcdb3eafe50 | 6ad95641ddc9be155108cd2297ce15bcd8cb0ca25c68bfc4fce3cbf5009a236a | c1ccc(CNCc2cn(Cc3ccccc3)c3ccccc23)cc1 | [C:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[CH3;D1;+0:5]>>[C:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[CH2;D2;+0:5]-[C;D1;H3:6] | null | [] | null | null | 2 | HOUR | To a magnetically stirred solution of methyl α-[3-(trifluoromethyl)benzylamino-]-1-benzylindole-3-acetate hydrochloride (100 mg) in 8 mL of ethanol was added 70 μL of 25% sodium methoxide in methanol. After stirring at room temperature for two hours, TLC analysis showed 90% conversion to the title compound.
Conditions:... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | c1ccccc1.c1ccccc1.c1c[nH]c2ccccc12 | Other | C(C)O.CO | null | 2 | COC(=O)C(NCc1cccc(C(F)(F)F)c1)c1cn(Cc2ccccc2)c2ccccc12>C(C)O.CO>CCOC(=O)C(NCc1cccc(C(F)(F)F)c1)c1cn(Cc2ccccc2)c2ccccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-60b3074aefe344eab4ea2ade849112af | Cl>>Cl | FC(C=1C=C(CNC(C(=O)OC)C2=CN(C3=CC=CC=C23)CC2=CC=CC=C2)C=CC1)(F)F.Cl>>Cl.FC(C=1C=C(CNC(C(=O)OC)C2=CN(C3=CC=CC=C23)CC2=CC=CC=C2)C=CC1)(F)F | [ClH:34]>>[ClH:34] | Cl | Cl | null | null | CCOCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 95 | [{"value": 95.0, "product": "Cl.FC(C=1C=C(CNC(C(=O)OC)C2=CN(C3=CC=CC=C23)CC2=CC=CC=C2)C=CC1)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A magnetically stirred solution of methyl α-[3-(trifluoromethyl)benzylamino]-1-benzylindole-3-acetate (4.07 g, 9.0 mmol) in 65 mL of ether cooled at 0°-5° C. was treated dropwise over a four-minute period with a stock solution of hydrogen chloride in ether (3.8 mL, 11.71 mmol, 1.3 eq, 3.1 mmol per mL). The cooling bath... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CCOCC | null | 8 | Cl>CCOCC>Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-21c30be098ec4f848e781425f347ffe0 | Cl>>Cl | FC(C=1C=C(CNC(C(=O)OCC)C2=CN(C3=CC=CC=C23)CC)C=CC1)(F)F.Cl>>Cl.FC(C=1C=C(CNC(C(=O)OCC)C2=CN(C3=CC=CC=C23)CC)C=CC1)(F)F | [ClH:30]>>[ClH:30] | Cl | Cl | null | null | CCOCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | 30 | MINUTE | Ethyl α-[3-(trifluoromethyl)benzylamino]-1-ethylindole-3-acetate (1.50 g, 3.70 mmol) was placed in 25 mL of ether, saturated with HCl gas and stirred under nitrogen for 30 minutes. The contents were concentrated to dryness in vacuo and the resulting solid recrystallized from acetone-ether (1:5) to give 1.30 g of the ti... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CCOCC | null | 0.5 | Cl>CCOCC>Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3f8581bc16ea4d41a3c766acc9b0ade0 | CCCCCC.COC(=O)C(NCc1cccc(C(F)(F)F)c1)c1c[nH]c2ccccc12.ClCc1ccc(Cl)cc1>>COC(=O)C(c1cn(Cc2ccc(Cl)cc2)c2ccccc12)N(C)Cc1cccc(C(F)(F)F)c1 | CCCCCC.C(C)(=O)OCC.ClC1=CC=C(CCl)C=C1.[H-].[Na+].FC(C=1C=C(CNC(C(=O)OC)C2=CNC3=CC=CC=C23)C=CC1)(F)F>>CN(C(C(=O)OC)C1=CN(C2=CC=CC=C12)CC1=CC=C(C=C1)Cl)CC1=CC(=CC=C1)C(F)(F)F | CCCCC[CH3:24].[CH3:1][O:2][C:3](=[O:4])[CH:5]([c:6]1[cH:7][nH:8][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12)[NH:23][CH2:25][c:26]1[cH:27][cH:28][cH:29][c:30]([C:31]([F:32])([F:33])[F:34])[cH:35]1.Cl[CH2:9][c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([c:6]1[cH:7][n:8]([CH2:9][c:10... | CCCCCC.COC(=O)C(NCc1cccc(C(F)(F)F)c1)c1c[nH]c2ccccc12.ClCc1ccc(Cl)cc1 | COC(=O)C(c1cn(Cc2ccc(Cl)cc2)c2ccccc12)N(C)Cc1cccc(C(F)(F)F)c1 | null | null | CN(C=O)C.CCOCC | Heteroatom Alkylation and Arylation | OtherReaction | c6ee39ced5d4143298d1037a6764569d0214d9628a7df282055ec75108f5a438 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CNCc2cn(Cc3ccccc3)c3ccccc23)cc1 | C-C-C-C-C-[CH3;D1;+0:1].Cl-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C:10](-[NH;D2;+0:11]-[C:12]-[c:13])-[c:14]1:[c:15]:[c:16](:[c:17]):[nH;D2;+0:18]:[c:19]:1>>[C;D1;H3:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C:10](-[N;H0;D3;+0:11](-[CH3;D1;+0:1])-[C:12]-[c:13])-[c:14]1:[c:15]:[c:16](:[c:17]):[n;... | null | [] | null | null | 10 | MINUTE | To a magnetically stirred suspension of sodium hydride (60% oil dispersion washed two times with hexane, 80 mg, 2.0 mmol) in 5 mL of dimethylformamide (DMF) under nitrogen was added methyl α-[3-(trifluoromethyl)benzylamino]-indole-3acetate (752 mg, 2.0 mmol) dissolved in 2 mL DMF. Stirring was continued at room tempera... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1c[nH]c2ccccc12 | c1ccccc1.c1c[nH]c2ccccc12.c1ccccc1 | HCl | CN(C=O)C.CCOCC | null | 0.166667 | CCCCCC.COC(=O)C(NCc1cccc(C(F)(F)F)c1)c1c[nH]c2ccccc12.ClCc1ccc(Cl)cc1>CN(C=O)C.CCOCC>COC(=O)C(c1cn(Cc2ccc(Cl)cc2)c2ccccc12)N(C)Cc1cccc(C(F)(F)F)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2ab8d445b07a4216a285e80f012a3dfa | COc1ccc2[nH]ccc2c1.NCc1cccc(C(F)(F)F)c1.O=CC(=O)O>>COC(=O)C(NCc1cccc(C(F)(F)F)c1)c1c[nH]c2ccc(OC)cc12 | COC=1C=C2C=CNC2=CC1.FC(C=1C=C(CN)C=CC1)(F)F.C(C)(=O)O.O.C(C=O)(=O)O>>FC(C=1C=C(C=CC1)CNC(C(=O)OC)C1=CNC2=CC=C(C=C12)OC)(F)F | [cH:18]1[cH:19][nH:20][c:21]2[cH:22][cH:23][c:24]([O:25][CH3:26])[cH:27][c:28]12.[NH2:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17]1.O=[CH:5][C:3]([OH:2])=[O:4]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([NH:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17]1)[c:18]1[c... | COc1ccc2[nH]ccc2c1.NCc1cccc(C(F)(F)F)c1.O=CC(=O)O | COC(=O)C(NCc1cccc(C(F)(F)F)c1)c1c[nH]c2ccc(OC)cc12 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 1ad28a17916661faa13d1595f9601d2e5842ade24e08e8306fdd72a883053031 | 97dbaca91fbe46a7e0670cff222de61ac85a7fcf864bf14fca6123c5a1a3812c | c1ccc(CNCc2c[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4].[NH2;D1;+0:5]-[C:6]-[c:7].[c:8]:[c:9]1:[#7;a:10]:[c:11]:[cH;D2;+0:12]:[c:13]:1:[c:14]>>[C;D1;H3:15]-[O;H0;D2;+0:4]-[C:2](=[O;D1;H0:3])-[CH;D3;+0:1](-[NH;D2;+0:5]-[C:6]-[c:7])-[c;H0;D3;+0:12]1:[c:11]:[#7;a:10]:[c:9](:[c:8]):[c:13]:1:[c:14] | null | [] | null | null | 3 | DAY | To a stirred solution of 7.24 g (41.34 mmoles) of 3-(trifluoromethyl)benzylamine and 4 mL (4.2 g, 69.88 mmoles) of acetic acid in 50 mL of MeOH was added a solution of 3.65 g (41.34 mmoles) of glyoxylic acid monohydrate in 50 mL of MeOH followed by 5.07 g (34.45 mmoles) of 5-methoxyindole. The resulting solution was al... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carboxylic acid.Primary amine | Ester.Secondary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | null | CO | null | 72 | COc1ccc2[nH]ccc2c1.NCc1cccc(C(F)(F)F)c1.O=CC(=O)O>CO>COC(=O)C(NCc1cccc(C(F)(F)F)c1)c1c[nH]c2ccc(OC)cc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-69fd0f6486c34ef8b949897a3d4dc910 | CCOC(=O)C(N)c1c[nH]c2ccccc12>>NC(C(=O)O)c1c[nH]c2ccccc12 | NC(C(=O)OCC)C1=CNC2=CC=CC=C12.[OH-].[Na+].CO>>NC(C(=O)O)C1=CNC2=CC=CC=C12 | CC[O:5][C:3]([CH:2]([NH2:1])[c:6]1[cH:7][nH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12)=[O:4]>>[NH2:1][CH:2]([C:3](=[O:4])[OH:5])[c:6]1[cH:7][nH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12 | CCOC(=O)C(N)c1c[nH]c2ccccc12 | NC(C(=O)O)c1c[nH]c2ccccc12 | null | null | C(C)(=O)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2[nH]ccc2c1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | 50 | MINUTE | A mixture of 2 g of ethyl α-aminoindole-3-acetate, excess dilute NaOH solution, and a few mL of MeOH was stirred occasionally for 25 minutes. Since a solution had not been obtained, the mixture was heated on a steam bath for ten minutes. The resulting solution was allowed to stand at ambient temperature for 50 minutes.... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2[nH]ccc2c1 | Other | C(C)(=O)O | null | 0.833333 | CCOC(=O)C(N)c1c[nH]c2ccccc12>C(C)(=O)O>NC(C(=O)O)c1c[nH]c2ccccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-07edbbd2cd764d6591514470ed57cfaa | COC(=O)C=O.NCCc1ccc(S(N)(=O)=O)cc1.c1ccc2[nH]ccc2c1>>NS(=O)(=O)c1ccc(CCNC(C(=O)O)c2c[nH]c3ccccc23)cc1.O | N1C=CC2=CC=CC=C12.NCCC1=CC=C(C=C1)S(=O)(=O)N.C(C)(=O)O.C(C=O)(=O)OC>>O.NS(=O)(=O)C1=CC=C(C=C1)CCNC(C(=O)O)C1=CNC2=CC=CC=C12 | C[O:15][C:13]([CH:12]=[O:27])=[O:14].[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][NH2:11])[cH:25][cH:26]1.[cH:16]1[cH:17][nH:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]12>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][NH:11][CH:12]([C:13](=[O:14])[OH:15])[c:16]2[cH:17][nH:1... | COC(=O)C=O.NCCc1ccc(S(N)(=O)=O)cc1.c1ccc2[nH]ccc2c1 | NS(=O)(=O)c1ccc(CCNC(C(=O)O)c2c[nH]c3ccccc23)cc1.O | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | a80af25249377d1b42548b94d6e944681d1777120ac835628ebb2925ed11199d | 4be68a8f2d238730b7d84250aa75cdaa35366d05903de952015a33135d01500f | c1ccc(CCNCc2c[nH]c3ccccc23)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[CH;D2;+0:4]=[O;H0;D1;+0:5].[C:6]-[C:7]-[NH2;D1;+0:8].[c:9]:[c:10]1:[#7;a:11]:[c:12]:[cH;D2;+0:13]:[c:14]:1:[c:15]>>[C:6]-[C:7]-[NH;D2;+0:8]-[CH;D3;+0:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1])-[c;H0;D3;+0:13]1:[c:12]:[#7;a:11]:[c:10](:[c:9]):[c:14]:1:[c:15].[OH2;D0;+0:5] | 63,355.6 | [{"value": 38.0, "product": "O.NS(=O)(=O)C1=CC=C(C=C1)CCNC(C(=O)O)C1=CNC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63355.6, "product": "O.NS(=O)(=O)C1=CC=C(C=C1)CCNC(C(=O)O)C1=CNC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | DAY | To a stirred solution of 6.01 g (0.03 mmole) of 4-(2-aminoethyl)benzenesulfonamide and 2.5 mL (2.62 g 0.044 mole) of acetic acid in 150 mL of MeOH was added a solution of 2.64 g (0.03 mole) of methyl glyoxylate in 50 mL of MeOH followed by 2.93 g (0.025 mole) of indole. Initially a solution was obtained. Soon solid beg... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester.Primary amine | Carboxylic acid.Secondary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | Other | CO | null | 96 | COC(=O)C=O.NCCc1ccc(S(N)(=O)=O)cc1.c1ccc2[nH]ccc2c1>CO>NS(=O)(=O)c1ccc(CCNC(C(=O)O)c2c[nH]c3ccccc23)cc1.O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-69d35a3bb1bc42339ef1b49a84e23b5f | COC(=O)C=O.NCc1ccccc1.c1ccc2[nH]ccc2c1>>COC(=O)C(NCc1ccccc1)c1c[nH]c2ccccc12 | N1C=CC2=CC=CC=C12.C(C1=CC=CC=C1)N.C(C)(=O)O.C(C=O)(=O)OC>>C1(=CC=CC=C1)CNC(C(=O)OC)C1=CNC2=CC=CC=C12 | O=[CH:5][C:3]([O:2][CH3:1])=[O:4].[NH2:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1.[cH:14]1[cH:15][nH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([NH:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[c:14]1[cH:15][nH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12 | COC(=O)C=O.NCc1ccccc1.c1ccc2[nH]ccc2c1 | COC(=O)C(NCc1ccccc1)c1c[nH]c2ccccc12 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 5595146384c598279112ebd7ba0cf5386a231bbdc1f289220bf12fba7cc91e05 | 58e20d8df59c2495160850d53d072962f7ab0829c937d9b002a0dd2d82d92775 | c1ccc(CNCc2c[nH]c3ccccc23)cc1 | O=[CH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[NH2;D1;+0:6]-[C:7]-[c:8].[c:9]:[c:10]1:[#7;a:11]:[c:12]:[cH;D2;+0:13]:[c:14]:1:[c:15]>>[C;D1;H3:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH;D3;+0:1](-[NH;D2;+0:6]-[C:7]-[c:8])-[c;H0;D3;+0:13]1:[c:12]:[#7;a:11]:[c:10](:[c:9]):[c:14]:1:[c:15] | 86.3 | [{"value": 86.3, "product": "C1(=CC=CC=C1)CNC(C(=O)OC)C1=CNC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 69 | HOUR | To a stirred solution of 6.43 g (0.06 mole) of benzylamine and 5 mL (5.25 g, 0.09 mole) of acetic acid in 50 mL of MeOH was added a solution of 5.28 g (0.06 mole) of methyl glyoxylate in 50 mL of MeOH followed by 5.86 g (0.05 mole) of indole. The resulting solution was allowed to stand for 69 hours. The solvent was eva... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester.Primary amine | Ester.Secondary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | HO- | CO | null | 69 | COC(=O)C=O.NCc1ccccc1.c1ccc2[nH]ccc2c1>CO>COC(=O)C(NCc1ccccc1)c1c[nH]c2ccccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c456b7da73ac4e6ca23b379fc52bb58b | COC(=O)CNc1ccccc1.O=Cc1cn(Cc2ccccc2)c2ccccc12>>COC(=O)C(NCc1cn(Cc2ccccc2)c2ccccc12)c1ccccc1 | [BH3-]C#N.[Na+].C1(=CC=CC=C1)CN1C=C(C2=CC=CC=C12)C=O.Cl.C1(=CC=CC=C1)NCC(=O)OC.CC(=O)O.CO>>C1(=CC=CC=C1)CN1C=C(C2=CC=CC=C12)CNC(C(=O)OC)C1=CC=CC=C1 | [CH3:1][O:2][C:3](=[O:4])[CH2:5][NH:6][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1.O=[CH:7][c:8]1[cH:9][n:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]12>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([NH:6][CH2:7][c:8]1[cH:9][n:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]... | COC(=O)CNc1ccccc1.O=Cc1cn(Cc2ccccc2)c2ccccc12 | COC(=O)C(NCc1cn(Cc2ccccc2)c2ccccc12)c1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 2394dddb06f5e80eb63aa57cb341e545bca55094f537ccd3ceb95ddec7356af1 | 345fa7989b6c7bd18d53834597527cc4f3089a81ee246a4b80121bb910b114a0 | c1ccc(CNCc2cn(Cc3ccccc3)c3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5](-[C:6]):[c:7]:1.[C;D1;H3:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[CH2;D2;+0:12]-[NH;D2;+0:13]-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[C:6]-[#7;a:5]1:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:13]-[CH;D3;+0:12](-[C:10](=[O;D1;H0:11])-[#8:9]-[C;D1;H3:8])-[c;H0;D3;+0:14](:[c:15]:... | 43 | [{"value": 43.0, "product": "C1(=CC=CC=C1)CN1C=C(C2=CC=CC=C12)CNC(C(=O)OC)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a suspension of methyl (+/-)-phenylglycinate hydrochloride (4.00 g, 19.8 mmol) in MeOH (50 mL), and HOAc (4 mL) was added 1-phenylmethyl-indole-3-carboxaldehyde (2.85 g, 12.1 mmol). The resulting mixture was allowed to stir at room temperature for 20 minutes; then NaBH3CN (1.98 g, 31.5 mmol) was added in one portion... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester.Secondary amine | Ester.Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1c[nH]c2ccccc12.c1ccccc1 | Other | null | null | 0.333333 | COC(=O)CNc1ccccc1.O=Cc1cn(Cc2ccccc2)c2ccccc12>>COC(=O)C(NCc1cn(Cc2ccccc2)c2ccccc12)c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c1c083a6f395481abe3df8731345c900 | C[Si](C)(Cl)Cl.N>>C[Si]1(C)N[Si](C)(C)N[Si](C)(C)N1 | C[Si](Cl)(Cl)C.N>>C[Si]1(N[Si](N[Si](N1)(C)C)(C)C)C | Cl[Si:2](Cl)([CH3:1])[CH3:7].[NH3:4]>>[CH3:1][Si:2]1([CH3:3])[NH:4][Si:5]([CH3:6])([CH3:7])[NH:8][Si:9]([CH3:10])([CH3:11])[NH:12]1 | C[Si](C)(Cl)Cl.N | C[Si]1(C)N[Si](C)(C)N[Si](C)(C)N1 | null | null | C1=CC=CC=C1 | Protection | OtherReaction | 14143e77eb8e0d2e8640f64675f2937ce6536749cb929538870537b809701eb3 | 69f9623d70f8449fc8a053886a4509e0600bee582fe9a4cd1a5c5e2782e4232a | N1[SiH2]N[SiH2]N[SiH2]1 | Cl-[Si;H0;D4;+0:1](-Cl)(-[C;D1;H3:2])-[CH3;D1;+0:3].[NH3;D0;+0:4]>>[C;D1;H3:2]-[Si;H0;D4;+0:1]1(-[C;D1;H3:5])-[#7:6]-[#14:7]-[#7:8]-[#14:9](-[C;D1;H3:10])(-[CH3;D1;+0:3])-[NH;D2;+0:4]-1 | null | [] | null | null | null | null | This method involves reacting dimethyldichlorosilane with ammonia in benzene at 30° C., removing ammonia chloride by-product by filtration through a glass filter or the like, and distilling the reaction product to isolate hexamethylcyclotrisilazane.
Conditions: See reaction.notes.procedure_details.
Workup: at 30° C.; r... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Secondary amine.Secondary amine.Secondary amine.Silyl protective group.Silyl protective group.Silyl protective group | null | N1[Si]N[Si]N[Si]1 | N1[Si]N[Si]N[Si]1 | null | C1=CC=CC=C1 | null | null | C[Si](C)(Cl)Cl.N>C1=CC=CC=C1>C[Si]1(C)N[Si](C)(C)N[Si](C)(C)N1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8e84db8ce536415d96651b7838d19504 | C[Si](C)(Cl)Cl.N>>C[Si]1(C)N[Si](C)(C)N[Si](C)(C)N1 | C[Si](Cl)(Cl)C.N>>C[Si]1(N[Si](N[Si](N1)(C)C)(C)C)C | Cl[Si:2](Cl)([CH3:1])[CH3:7].[NH3:4]>>[CH3:1][Si:2]1([CH3:3])[NH:4][Si:5]([CH3:6])([CH3:7])[NH:8][Si:9]([CH3:10])([CH3:11])[NH:12]1 | C[Si](C)(Cl)Cl.N | C[Si]1(C)N[Si](C)(C)N[Si](C)(C)N1 | null | null | C1(=CC=CC=C1)C | Protection | OtherReaction | 14143e77eb8e0d2e8640f64675f2937ce6536749cb929538870537b809701eb3 | 69f9623d70f8449fc8a053886a4509e0600bee582fe9a4cd1a5c5e2782e4232a | N1[SiH2]N[SiH2]N[SiH2]1 | Cl-[Si;H0;D4;+0:1](-Cl)(-[C;D1;H3:2])-[CH3;D1;+0:3].[NH3;D0;+0:4]>>[C;D1;H3:2]-[Si;H0;D4;+0:1]1(-[C;D1;H3:5])-[#7:6]-[#14:7]-[#7:8]-[#14:9](-[C;D1;H3:10])(-[CH3;D1;+0:3])-[NH;D2;+0:4]-1 | 42.1 | [{"value": 42.0, "product": "C[Si]1(N[Si](N[Si](N1)(C)C)(C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.1, "product": "C[Si]1(N[Si](N[Si](N1)(C)C)(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A 500-ml, four-necked flask equipped with a stirrer, dry ice/acetone condenser, thermometer, and gas inlet tube was charged with 64.5 grams (0.5 mol) of dimethyldichlorosilane and 150 grams of toluene. Into the solution at 30° C., 52 grams (3.06 mol) of ammonia was blown over 2 hours for effecting reaction. At the end ... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Secondary amine.Secondary amine.Secondary amine.Silyl protective group.Silyl protective group.Silyl protective group | null | N1[Si]N[Si]N[Si]1 | N1[Si]N[Si]N[Si]1 | null | C1(=CC=CC=C1)C | null | null | C[Si](C)(Cl)Cl.N>C1(=CC=CC=C1)C>C[Si]1(C)N[Si](C)(C)N[Si](C)(C)N1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-fabc61b31cd147d983caa87d8e7474d5 | CCCCCCBr.COC(=O)CC(C)=O>>CCCCCCC(C(C)=O)C(=O)OC | C(CC(=O)C)(=O)OC.C[O-].[Na+].BrCCCCCC>>C(C)(=O)C(C(=O)OC)CCCCCC | Br[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].[CH2:7]([C:8]([CH3:9])=[O:10])[C:11](=[O:12])[O:13][CH3:14]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([C:8]([CH3:9])=[O:10])[C:11](=[O:12])[O:13][CH3:14] | CCCCCCBr.COC(=O)CC(C)=O | CCCCCCC(C(C)=O)C(=O)OC | null | null | CO | C-C Coupling | OtherReaction | eb3faf2a43700925ab4f46cf65072b7145e4e060dba25a917e6b7428f38e349e | 61bad66347ae366bfd0a2cd3779dd3d0c29125e97564b97243e11258be3b2a9f | null | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[C:9](-[C;D1;H3:10])=[O;D1;H0:11]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[CH;D3;+0:8](-[C:6](=[O;D1;H0:7])-[#8:5]-[C;D1;H3:4])-[C:9](-[C;D1;H3:10])=[O;D1;H0:11] | 62.3 | [{"value": 62.3, "product": "C(C)(=O)C(C(=O)OC)CCCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 465 g of methyl acetoacetate were added dropwise under nitrogen and stirring to 720 g of 30% sodium methylate solution in 1200 ml of methanol. Then, 727 g of 1-bromohexane were added and the reaction mixture was boiled at reflux for 20 hours. The majority of the methanol was distilled off and the residue was poured on ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone.Ester | null | null | null | HBr | CO | null | null | CCCCCCBr.COC(=O)CC(C)=O>CO>CCCCCCC(C(C)=O)C(=O)OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3394f386594347eeac4f17cc00376730 | Cc1ccccc1.O=C(OC(=O)c1ccccc1)c1ccccc1.[O-][Cl+3]([O-])([O-])O>>CCCCCCCCCCCC1CC(OC(=O)c2ccccc2)C(CCCCCC)C(=O)O1 | C1(=CC=CC=C1)C.C(C1=CC=CC=C1)(=O)OC(C1=CC=CC=C1)=O.Cl(=O)(=O)(=O)O>>C(C1=CC=CC=C1)(=O)OC1C(C(=O)OC(C1)CCCCCCCCCCC)CCCCCC | [cH:1]1[cH:2][cH:13][c:12]([CH3:11])[cH:29][cH:30]1.[cH:14]1[c:24]([C:31]([O:15][C:16](=[O:17])[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)=[O:33])[cH:25][cH:26][cH:27][cH:28]1.[O-][Cl+3]([O-])(O)[O-:32]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]1[CH2:13][CH:14]([O:15][C:16]... | Cc1ccccc1.O=C(OC(=O)c1ccccc1)c1ccccc1.[O-][Cl+3]([O-])([O-])O | CCCCCCCCCCCC1CC(OC(=O)c2ccccc2)C(CCCCCC)C(=O)O1 | null | null | null | C-C Coupling | OtherReaction | c9cfa63c20444de92fcef08b02d1254bf21ad8bd4547a1cfeebe9628108651e7 | f4f0e4933e28ad003609fc57514057fc8dd4673f5e354908bb247868372e8d2b | O=C1CC(OC(=O)c2ccccc2)CCO1 | O-[Cl+3](-[O-;H0;D1:1])(-[O-])-[O-].[CH3;D1;+0:2]-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:[cH;D2;+0:8]:1.[O;D1;H0:9]=[C:10](-[c:11])-[O;H0;D2;+0:12]-[C;H0;D3;+0:13](=[O;H0;D1;+0:14])-[c;H0;D3;+0:15]1:[cH;D2;+0:16]:[cH;D2;+0:17]:[cH;D2;+0:18]:[cH;D2;+0:19]:[cH;D2;+0:20]:1>>[C:21]-[C:22]-[CH2;... | 103.4 | [{"value": 103.4, "product": "C(C1=CC=CC=C1)(=O)OC1C(C(=O)OC(C1)CCCCCCCCCCC)CCCCCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 177.3 g of the δ-lactone from c) were suspended in 1250 ml of toluene while stirring. After the addition of 138.6 g of benzoic anhydride the mixture was stirred for 10 minutes. Then, 2.5 ml of perchloric acid were added. The mixture was stirred for a further 2.5 hours. The reaction solution was extracted in toluene wit... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester | Ester.Ester | c1ccccc1.c1ccccc1 | C1CCOCC1 | C1CCOCC1.c1ccccc1 | null | null | null | null | Cc1ccccc1.O=C(OC(=O)c1ccccc1)c1ccccc1.[O-][Cl+3]([O-])([O-])O>>CCCCCCCCCCCC1CC(OC(=O)c2ccccc2)C(CCCCCC)C(=O)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7aa6ea05ad5f4e639b91d1a44ecf298b | CCCCCCCCCCC[C@@H](O)CC(=O)OC.N=C(OCc1ccccc1)C(Cl)(Cl)Cl>>CCCCCCCCCCC[C@H](CC(=O)OC)OCc1ccccc1 | O[C@@H](CC(=O)OC)CCCCCCCCCCC.ClC(C(OCC1=CC=CC=C1)=N)(Cl)Cl.FC(S(=O)(=O)O)(F)F>>C(C1=CC=CC=C1)O[C@@H](CC(=O)OC)CCCCCCCCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C@H:12]([CH2:13][C:14](=[O:15])[O:16][CH3:17])[OH:18].N=C(O[CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1)C(Cl)(Cl)Cl>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C@H:12]([CH2:13][C:14](=[O:15])[O:16... | CCCCCCCCCCC[C@@H](O)CC(=O)OC.N=C(OCc1ccccc1)C(Cl)(Cl)Cl | CCCCCCCCCCC[C@H](CC(=O)OC)OCc1ccccc1 | null | null | C1CCCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | e1602c7639e9590c57e1f519302834b854314fa06b50f2e00792e7923548c28a | 9939e71487b269001d097fe9b7393354dcb141bf54208fca597f111e50af4454 | c1ccccc1 | Cl-C(-Cl)(-Cl)-C(=N)-O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C:9](-[C:10])-[OH;D1;+0:11]>>[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C:9](-[C:10])-[O;H0;D2;+0:11]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 112.8 | [{"value": 112.8, "product": "C(C1=CC=CC=C1)O[C@@H](CC(=O)OC)CCCCCCCCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 206.7 g of methyl (R)-3-hydroxytetradecanoate in 1000 ml of cyclohexane was treated under nitrogen and while stirring with 214.2 g of benzyl trichloroacetimidate and dissolved at 20°. 10 ml of trifluoromethanesulphonic acid were added dropwise while cooling in an ice/water bath in such a manner that the... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Ether.Secondary alcohol | Ether | null | null | c1ccccc1 | HCl | C1CCCCC1 | null | null | CCCCCCCCCCC[C@@H](O)CC(=O)OC.N=C(OCc1ccccc1)C(Cl)(Cl)Cl>C1CCCCC1>CCCCCCCCCCC[C@H](CC(=O)OC)OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3778de4bf8bd4957a0ab8fe7b5d88d63 | CCCCCCCCCCC[C@@H](O)CC(=O)OC>>CCCCCCCCCCC[C@@H](O)CC(=O)O | O[C@@H](CC(=O)OC)CCCCCCCCCCC.O1CCOCC1.[OH-].[Na+]>>O[C@@H](CC(=O)O)CCCCCCCCCCC | C[O:17][C:15]([CH2:14][C@@H:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[OH:13])=[O:16]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C@@H:12]([OH:13])[CH2:14][C:15](=[O:16])[OH:17] | CCCCCCCCCCC[C@@H](O)CC(=O)OC | CCCCCCCCCCC[C@@H](O)CC(=O)O | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | null | 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] | 98 | [{"value": 98.0, "product": "O[C@@H](CC(=O)O)CCCCCCCCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.9, "product": "O[C@@H](CC(=O)O)CCCCCCCCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Under nitrogen and while stirring there were added dropwise to a solution of 129.2 g of methyl (R)-3-hydroxytetradecanoate, 1033 ml of dioxan and 122.9 g of 28 percent sodium hydroxide solution. 77.5 ml of methanol were added dropwise to the solution. After stirring for a further 1.5 hours the resulting suspension was ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | null | Other | CO | null | null | CCCCCCCCCCC[C@@H](O)CC(=O)OC>CO>CCCCCCCCCCC[C@@H](O)CC(=O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-355ce15f03e04745bfb0f379e76f61c0 | CCCCCCBr.COC(=O)CC(=O)OC>>CCCCCCC(C(=O)OC)C(=O)OC | O.C[O-].[Na+].C(CC(=O)OC)(=O)OC.BrCCCCCC>>C(CCCCC)C(C(=O)OC)C(=O)OC | Br[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].[CH2:7]([C:8](=[O:9])[O:10][CH3:11])[C:12](=[O:13])[O:14][CH3:15]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([C:8](=[O:9])[O:10][CH3:11])[C:12](=[O:13])[O:14][CH3:15] | CCCCCCBr.COC(=O)CC(=O)OC | CCCCCCC(C(=O)OC)C(=O)OC | null | null | CO | C-C Coupling | OtherReaction | 8175b6573d6439ec7ccc45bf6b48843ab56b46dccfc6504384c4766d09f35cc7 | d1817e44576d3a158547867a56245217a593d4f828a6d6dfaa8ed11276894e44 | null | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[CH;D3;+0:8](-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12])-[C:6](=[O;D1;H0:7])-[#8:5]-[C;D1;H3:4] | 78.3 | [{"value": 78.3, "product": "C(CCCCC)C(C(=O)OC)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.3, "product": "C(CCCCC)C(C(=O)OC)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 350.1 g of 30 percent sodium methylate solution in methanol were diluted with 550 ml of methanol under nitrogen and while stirring. 264.2 g of dimethyl malonate were added dropwise. After warming the suspension to 40° 321.0 g of 1-bromohexane were added dropwise. After stirring at 40° for 1 hour, under reflux for 2 hou... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester | Ester.Ester | null | null | null | HBr | CO | null | null | CCCCCCBr.COC(=O)CC(=O)OC>CO>CCCCCCC(C(=O)OC)C(=O)OC |
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