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-27da8e1d973d4c9ba83f51d41249d0ee | CC(=O)N=c1sc(C)cn1-c1cccc(C(F)(F)F)c1>>Cc1cn(-c2cccc(C(F)(F)F)c2)c(=N)s1 | C(C)(=O)N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)C.Cl>>N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)C | CC(=O)[N:16]=[c:15]1[n:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]2)[cH:3][c:2]([CH3:1])[s:17]1>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]2)[c:15](=[NH:16])[s:17]1 | CC(=O)N=c1sc(C)cn1-c1cccc(C(F)(F)F)c1 | Cc1cn(-c2cccc(C(F)(F)F)c2)c(=N)s1 | null | null | C(C)O.O | Reduction | OtherReaction | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | N=c1sccn1-c1ccccc1 | C-C(=O)-[N;H0;D2;+0:1]=[c:2]1:[#16;a:3]:[c:4]:[c:5]:[#7;a:6]:1-[c:7]>>[NH;D1;+0:1]=[c:2]1:[#16;a:3]:[c:4]:[c:5]:[#7;a:6]:1-[c:7] | 46.5 | [{"value": 46.5, "product": "N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-(acetylimino)-3-(3-trifluoromethylphenyl)-5-methylthiazoline (1 g) and hydrochloric acid (38 %, 4 ml) in ethanol-water (1:2, 15 ml) was refluxed for 3 hours. Ethanol was removed by distillation under reduced pressure, and the residue was neutralized with potassium carbonate, extracted with ethyl acetate ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1cscn1.c1ccccc1 | HO- | C(C)O.O | null | null | CC(=O)N=c1sc(C)cn1-c1cccc(C(F)(F)F)c1>C(C)O.O>Cc1cn(-c2cccc(C(F)(F)F)c2)c(=N)s1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c55f62cea29848c7bf7668db86abb1e9 | CCOC(=O)N=c1sc(Br)cn1-c1cccc(C(F)(F)F)c1>>CCOC(=O)N=c1sccn1-c1cccc(C(F)(F)F)c1 | C(C)OC(=O)N=C1SC(=CN1C1=CC(=CC=C1)C(F)(F)F)Br.C(CCC)[SnH](CCCC)CCCC.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O>>C(C)OC(=O)N=C1SC=CN1C1=CC(=CC=C1)C(F)(F)F | Br[c:9]1[s:8][c:7](=[N:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[n:11](-[c:12]2[cH:13][cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21]2)[cH:10]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]=[c:7]1[s:8][cH:9][cH:10][n:11]1-[c:12]1[cH:13][cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21]1 | CCOC(=O)N=c1sc(Br)cn1-c1cccc(C(F)(F)F)c1 | CCOC(=O)N=c1sccn1-c1cccc(C(F)(F)F)c1 | null | null | O1CCCC1 | Functional Group Interconversion | Aromatic dehalogenation | 4f6106989807e1170e2da8f2e1925119dcd1a22ece2cb0c7a904100c5bae54f5 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | N=c1sccn1-c1ccccc1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[#7;a:4](-[c:5]):[c:6]:1>>[c:5]-[#7;a:4]1:[c:6]:[cH;D2;+0:1]:[#16;a:2]:[c:3]:1 | 75.8 | [{"value": 75.8, "product": "C(C)OC(=O)N=C1SC=CN1C1=CC(=CC=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-ethoxycarbonylimino-3-(3-trifluoromethylphenyl)-5-bromothiazoline (4.7 g), tributyltin hydride (6.9 g) and a catalytic amount of benzoyl peroxide in tetrahydrofuran (100 ml) was refluxed for 10 hours. The solvent was removed by distillation, and the residue was washed with hexane. Recrystallization from... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cscn1 | c1cscn1 | c1cscn1.c1ccccc1 | Br- | O1CCCC1 | null | null | CCOC(=O)N=c1sc(Br)cn1-c1cccc(C(F)(F)F)c1>O1CCCC1>CCOC(=O)N=c1sccn1-c1cccc(C(F)(F)F)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-03cf8a9450bf45e38bbedbaf7ee743f1 | CC=CCN(C(=S)NC(=O)OCC)c1cccc(C(F)(F)F)c1>>CC=CCN(C(N)=S)c1cccc(C(F)(F)F)c1 | C(C=CC)N(C(=S)NC(=O)OCC)C1=CC(=CC=C1)C(F)(F)F.C[O-].[Na+]>>C(C=CC)N(C(=S)N)C1=CC(=CC=C1)C(F)(F)F | CCOC(=O)[NH:7][C:6]([N:5]([CH2:4][CH:3]=[CH:2][CH3:1])[c:9]1[cH:10][cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18]1)=[S:8]>>[CH3:1][CH:2]=[CH:3][CH2:4][N:5]([C:6]([NH2:7])=[S:8])[c:9]1[cH:10][cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18]1 | CC=CCN(C(=S)NC(=O)OCC)c1cccc(C(F)(F)F)c1 | CC=CCN(C(N)=S)c1cccc(C(F)(F)F)c1 | null | null | CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 594e00c7c96b76cceef88e84b84e3b15c8ccccf89b962b4acfdce59b315169f0 | 2fc6be7095b4a5f0c4afd24643297a35f2252040d56517b70efbfde0b1038b8a | c1ccccc1 | C-C-O-C(=O)-[NH;D2;+0:1]-[C:2](=[S;D1;H0:3])-[#7:4](-[c:5])-[C:6]-[C:7]=[C:8]>>[C:8]=[C:7]-[C:6]-[#7:4](-[c:5])-[C:2](-[NH2;D1;+0:1])=[S;D1;H0:3] | 50.5 | [{"value": 50.5, "product": "C(C=CC)N(C(=S)N)C1=CC(=CC=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of N-crotyl-N-(3-trifluoromethylphenyl)-N'-ethoxycarbonylthiourea (6 g) and sodium methoxide (28 % methanolic solution; 6.6 g) in methanol (100 ml) was refluxed for 2 days. After removal of the solvent, the residue was extracted with chloroform, washed with water and dried over anhydrous magnesium sulfate. T... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Thiourea | Thiourea | null | null | c1ccccc1 | HO- | CO | null | null | CC=CCN(C(=S)NC(=O)OCC)c1cccc(C(F)(F)F)c1>CO>CC=CCN(C(N)=S)c1cccc(C(F)(F)F)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7abe0b247b3646b18c986acb76de854f | CC(Br)Br.NC(=S)Nc1cccc(C(F)(F)F)c1>>N=C1SCCN1c1cccc(C(F)(F)F)c1 | FC(C=1C=C(C=CC1)NC(=S)N)(F)F.BrC(C)Br.C([O-])([O-])=O.[K+].[K+]>>N=C1SCCN1C1=CC(=CC=C1)C(F)(F)F | Br[CH:5](Br)[CH3:4].[NH2:1][C:2](=[S:3])[NH:6][c:7]1[cH:8][cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16]1>>[NH:1]=[C:2]1[S:3][CH2:4][CH2:5][N:6]1[c:7]1[cH:8][cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16]1 | CC(Br)Br.NC(=S)Nc1cccc(C(F)(F)F)c1 | N=C1SCCN1c1cccc(C(F)(F)F)c1 | null | null | CC(=O)C | Protection | OtherReaction | 8c754bee2a863613e7708520561d09055ee64cc3793115f8e576e60bae5af171 | 101460e55348dc63801d065e571f149bdadd19d7ea2f7cddc1402a217c094fa3 | N=C1SCCN1c1ccccc1 | Br-[CH;D3;+0:1](-Br)-[CH3;D1;+0:2].[NH2;D1;+0:3]-[C;H0;D3;+0:4](=[S;H0;D1;+0:5])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[NH;D1;+0:3]=[C;H0;D3;+0:4]1-[S;H0;D2;+0:5]-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6]-1-[c:7](:[c:8]):[c:9] | 110 | [{"value": 110.0, "product": "N=C1SCCN1C1=CC(=CC=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of N-(3-trifluoromethylphenyl)thiourea (6.1 g), dibromoethane (5.7 g) and anhydrous potassium carbonate (11.5 g) in acetone (60 ml) was refluxed for 1 day. The solvent was removed by distillation therefrom, and the residue was extracted with ethyl ether, washed with water, dried over anhydrous magnesium sulf... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide.Thiourea | Tertiary amine.Monosulfide | null | C1CSC[NH]1 | C1CSC[NH]1.c1ccccc1 | HBr | CC(=O)C | null | null | CC(Br)Br.NC(=S)Nc1cccc(C(F)(F)F)c1>CC(=O)C>N=C1SCCN1c1cccc(C(F)(F)F)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2646e83101e44194b575c8e4dfed9fd9 | CCCCOC(=O)Cl.N=C1SCCN1c1cccc(C(F)(F)F)c1>>CCCCOC(=O)N=C1SCCN1c1cccc(C(F)(F)F)c1 | N=C1SCCN1C1=CC(=CC=C1)C(F)(F)F.C(OCCCC)(=O)Cl.C(C)N(CC)CC>>C(CCC)OC(=O)N=C1SCCN1C1=CC(=CC=C1)C(F)(F)F | Cl[C:6]([O:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:7].[NH:8]=[C:9]1[S:10][CH2:11][CH2:12][N:13]1[c:14]1[cH:15][cH:16][cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:23]1>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][C:6](=[O:7])[N:8]=[C:9]1[S:10][CH2:11][CH2:12][N:13]1[c:14]1[cH:15][cH:16][cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:... | CCCCOC(=O)Cl.N=C1SCCN1c1cccc(C(F)(F)F)c1 | CCCCOC(=O)N=C1SCCN1c1cccc(C(F)(F)F)c1 | null | null | O1CCCC1 | Acylation | OtherReaction | f82c583524f79166411cb496627fa3c85d4aefc3413e305ade9275efe2428bc2 | d03c43b1eb3e007d0a26c663cd0f6b51f594c27d1ade9616fb1640d35a60bddb | N=C1SCCN1c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[NH;D1;+0:5]=[C:6]1-[#16:7]-[C:8]-[C:9]-[#7:10]-1-[c:11]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D2;+0:5]=[C:6]1-[#16:7]-[C:8]-[C:9]-[#7:10]-1-[c:11] | 40.5 | [{"value": 40.5, "product": "C(CCC)OC(=O)N=C1SCCN1C1=CC(=CC=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of N-(3-trifluoromethylphenyl)thiourea (6.1 g), dibromoethane (5.7 g) and anhydrous potassium carbonate (11.5 g) in acetone (60 ml) was refluxed for 1 day. The solvent was removed by distillation therefrom, and the residue was extracted with ethyl ether, washed with water, dried over anhydrous magnesium sulf... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether | Ether | null | null | C1CSC[NH]1.c1ccccc1 | HCl | O1CCCC1 | null | null | CCCCOC(=O)Cl.N=C1SCCN1c1cccc(C(F)(F)F)c1>O1CCCC1>CCCCOC(=O)N=C1SCCN1c1cccc(C(F)(F)F)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-fa8d09f785da43d08f3fafc57bc6778e | CC(Br)Br.CCOC(=O)NC(=S)Nc1cccc(C(F)(F)F)c1>>CCOC(=O)N=C1SCCN1c1cccc(C(F)(F)F)c1 | FC(C=1C=C(C=CC1)NC(=S)NC(=O)OCC)(F)F.BrC(C)Br.C([O-])([O-])=O.[K+].[K+]>>C(C)OC(=O)N=C1SCCN1C1=CC(=CC=C1)C(F)(F)F | Br[CH:10](Br)[CH3:9].[CH3:1][CH2:2][O:3][C:4](=[O:5])[NH:6][C:7](=[S:8])[NH:11][c:12]1[cH:13][cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]=[C:7]1[S:8][CH2:9][CH2:10][N:11]1[c:12]1[cH:13][cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21]1 | CC(Br)Br.CCOC(=O)NC(=S)Nc1cccc(C(F)(F)F)c1 | CCOC(=O)N=C1SCCN1c1cccc(C(F)(F)F)c1 | null | null | CC(=O)C | Protection | OtherReaction | d6f618ec53b6862d1ff2960c4e6a2b010fc7d1f3fee77a86188252744c890acc | 6f23c5b879e9820f6e48620bc2d18d56d8fa8f76fe736e09f5876deb392a7395 | N=C1SCCN1c1ccccc1 | Br-[CH;D3;+0:1](-Br)-[CH3;D1;+0:2].[C:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[C;H0;D3;+0:8](=[S;H0;D1;+0:9])-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[N;H0;D2;+0:7]=[C;H0;D3;+0:8]1-[S;H0;D2;+0:9]-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:10]-1-[c:11](:[c:12]):[c:13] | 83.1 | [{"value": 83.1, "product": "C(C)OC(=O)N=C1SCCN1C1=CC(=CC=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of N-(3-trifluoromethylphenyl)-N'-ethoxycarbonylthiourea (1.8 g), dibromoethane (1.29 g) and anhydrous potassium carbonate (2.6 g) in acetone (20 ml) was refluxed for 5 hours. The solvent was removed by distillation, and the residue was extracted with diethyl ether. The extract was washed with water, dried o... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide.Carbamic ester.Thiourea | Tertiary amine.Monosulfide | null | C1CSC[NH]1 | C1CSC[NH]1.c1ccccc1 | HBr | CC(=O)C | null | null | CC(Br)Br.CCOC(=O)NC(=S)Nc1cccc(C(F)(F)F)c1>CC(=O)C>CCOC(=O)N=C1SCCN1c1cccc(C(F)(F)F)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-05aff642a9524aeeb782b83184544cc8 | CC(C)C(C)(N)C(N)=O.CCOC(=O)c1cnc(C)nc1C(=O)OCC>>Cc1ncc(C(=O)O)c(C2=NC(C)(C(C)C)C(=O)N2)n1 | CC1=NC=C(C(=N1)C(=O)OCC)C(=O)OCC.NC(C(=O)N)(C(C)C)C>>CC1=NC=C(C(=N1)C=1NC(C(N1)(C(C)C)C)=O)C(=O)O | [NH2:11][C:12]([CH3:13])([CH:14]([CH3:15])[CH3:16])[C:17](=[O:18])[NH2:19].CCO[C:10](=O)[c:9]1[c:5]([C:6](=[O:7])[O:8]CC)[cH:4][n:3][c:2]([CH3:1])[n:20]1>>[CH3:1][c:2]1[n:3][cH:4][c:5]([C:6](=[O:7])[OH:8])[c:9]([C:10]2=[N:11][C:12]([CH3:13])([CH:14]([CH3:15])[CH3:16])[C:17](=[O:18])[NH:19]2)[n:20]1 | CC(C)C(C)(N)C(N)=O.CCOC(=O)c1cnc(C)nc1C(=O)OCC | Cc1ncc(C(=O)O)c(C2=NC(C)(C(C)C)C(=O)N2)n1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 3b698ee4f54c66f1d46998658008290900266bbd2feba49593a4d93a59594863 | eb44f496e8f1313af2c0f91b3e3b1cbaaa1a96970b8e4c17561608a8e6dd9f5a | O=C1CN=C(c2ccncn2)N1 | C-C-O-[C;H0;D3;+0:1](=O)-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1-[C:8](=[O;D1;H0:9])-[O;H0;D2;+0:10]-C-C.[C:11]-[C:12](-[C;D1;H3:13])(-[NH2;D1;+0:14])-[C:15](-[NH2;D1;+0:16])=[O;D1;H0:17]>>[C:11]-[C:12]1(-[C;D1;H3:13])-[N;H0;D2;+0:14]=[C;H0;D3;+0:1](-[c:2]2:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:2-[C:8](=[O;D1;H0:9])... | 51.5 | [{"value": 51.0, "product": "CC1=NC=C(C(=N1)C=1NC(C(N1)(C(C)C)C)=O)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.5, "product": "CC1=NC=C(C(=N1)C=1NC(C(N1)(C(C)C)C)=O)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 16 | HOUR | To a mixture of 98.8 g (0.415 mole) of diethyl 2-methylpyrimidine-4,5-dicarboxylate (compare, for example, J. Heterocycl. Chem. 2, 202-204 [1965]) and 54.0 g (0.415 mole) of 2-amino-2,3-dimethylbutyramide in 700 ml of anhydrous toluene there are added in portions 102.2 g (0.913 mole) of potassium tert.-butylate, and th... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary amide.Primary amine | Carboxylic acid.Secondary amide | null | C1=NCCN1 | c1cncnc1.C1=NCCN1 | HO- | C1(=CC=CC=C1)C | 80 | 16 | CC(C)C(C)(N)C(N)=O.CCOC(=O)c1cnc(C)nc1C(=O)OCC>C1(=CC=CC=C1)C>Cc1ncc(C(=O)O)c(C2=NC(C)(C(C)C)C(=O)N2)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-cac5b60f283041dda7c7abbd2044a9b6 | CCOC(=O)c1nc(SC)sc1C(=O)OCC>>CCOC(=O)c1nc(SC)sc1C(=O)O | [OH-].[Na+].CSC=1SC(=C(N1)C(=O)OCC)C(=O)OCC>>C(C)OC(=O)C=1N=C(SC1C(=O)O)SC | CC[O:15][C:13]([c:12]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[n:7][c:8]([S:9][CH3:10])[s:11]1)=[O:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]([S:9][CH3:10])[s:11][c:12]1[C:13](=[O:14])[OH:15] | CCOC(=O)c1nc(SC)sc1C(=O)OCC | CCOC(=O)c1nc(SC)sc1C(=O)O | null | null | O.C(C)O.O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1cscn1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[#16;a:5]):[c:6]:[#7;a:7]>>[#16;a:5]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[c:6]:[#7;a:7] | null | [] | null | null | 1 | HOUR | At room temperature, a solution of 1.10 g (27.5 mmol) of sodium hydroxide in 10 ml of water was added over a period of one hour to a solution of 7.00 g (25 mmol) of diethyl 2-methylthiothiazole-4,5-dicarboxylate in 100 ml of ethanol/water (2:1). The mixture was stirred for one hour, the solvent mixture was then removed... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cscn1 | Other | O.C(C)O.O | null | 1 | CCOC(=O)c1nc(SC)sc1C(=O)OCC>O.C(C)O.O>CCOC(=O)c1nc(SC)sc1C(=O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c86211829d6b4c1584a76548e6ee953b | CC(C)(C)NC(=O)c1csc(Br)n1.C[O-]>>COc1nc(C(=O)NC(C)(C)C)cs1 | C[O-].[Na+].C(C)(C)(C)NC(=O)C=1N=C(SC1)Br>>C(C)(C)(C)NC(=O)C=1N=C(SC1)OC | Br[c:3]1[n:4][c:5]([C:6](=[O:7])[NH:8][C:9]([CH3:10])([CH3:11])[CH3:12])[cH:13][s:14]1.[CH3:1][O-:2]>>[CH3:1][O:2][c:3]1[n:4][c:5]([C:6](=[O:7])[NH:8][C:9]([CH3:10])([CH3:11])[CH3:12])[cH:13][s:14]1 | CC(C)(C)NC(=O)c1csc(Br)n1.C[O-] | COc1nc(C(=O)NC(C)(C)C)cs1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 361dd26d5fe71f37e48dfadda08834dc24dbeb11757b91bcc09fe7edbef36ae1 | 51fd03eb6a688046e417b9ed09ea0e72062396d005af1318b9b5f376a97da959 | c1cscn1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4](-[C:5](-[#7:6])=[O;D1;H0:7]):[#7;a:8]:1.[C;D1;H3:9]-[O-;H0;D1:10]>>[#7:6]-[C:5](=[O;D1;H0:7])-[c:4]1:[#7;a:8]:[c;H0;D3;+0:1](-[O;H0;D2;+0:10]-[C;D1;H3:9]):[#16;a:2]:[c:3]:1 | 98 | [{"value": 98.0, "product": "C(C)(C)(C)NC(=O)C=1N=C(SC1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.4, "product": "C(C)(C)(C)NC(=O)C=1N=C(SC1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | At 25° C., 8.90 g of a 30% strength solution (49 mmol) of sodium methanolate in methanol was added to a solution of 12.00 g (46 mmol) of 2-bromothiazole-4-carboxylic acid-tert.-butylamide in 150 ml of methanol. The mixture was boiled under reflux for four hours, the clear solution was evaporated down, the residue was t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | c1cscn1 | c1cscn1 | c1cscn1 | Br- | CO | null | null | CC(C)(C)NC(=O)c1csc(Br)n1.C[O-]>CO>COc1nc(C(=O)NC(C)(C)C)cs1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7521a5ff0c9d4c75bde504a8fa790722 | CC(C)c1nc(C(=O)O)co1.NC1CC1>>CC(C)c1nc(C(=O)NC2CC2)co1 | S(=O)(Cl)Cl.C1(CC1)N.O.C(C)(C)C=1OC=C(N1)C(=O)O>>C1(CC1)NC(=O)C=1N=C(OC1)C(C)C | O[C:7]([c:6]1[n:5][c:4]([CH:2]([CH3:1])[CH3:3])[o:14][cH:13]1)=[O:8].[NH2:9][CH:10]1[CH2:11][CH2:12]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][c:6]([C:7](=[O:8])[NH:9][CH:10]2[CH2:11][CH2:12]2)[cH:13][o:14]1 | CC(C)c1nc(C(=O)O)co1.NC1CC1 | CC(C)c1nc(C(=O)NC2CC2)co1 | null | null | CN(C=O)C.C1(=CC=CC=C1)C.ClCCl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NC1CC1)c1cocn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#8;a:6]:[c:7]:1.[NH2;D1;+0:8]-[C:9]1-[C:10]-[C:11]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:8]-[C:9]1-[C:10]-[C:11]-1)-[c:3]1:[#7;a:4]:[c:5]:[#8;a:6]:[c:7]:1 | 96 | [{"value": 96.0, "product": "C1(CC1)NC(=O)C=1N=C(OC1)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.8, "product": "C1(CC1)NC(=O)C=1N=C(OC1)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 1 | HOUR | At room temperature, 47.6 g (0.40 mol) of thionyl chloride was dripped into a solution of 31.0 g (0.20 mol) of 2-isopropyloxazole-4-carboxylic acid in 200 ml of toluene and 2 ml of dimethylformamide, and the mixture was stirred for one hour at 80° C. The solvents were stripped off under reduced pressure, the residue wa... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1cocn1.C1CC1 | HO- | CN(C=O)C.C1(=CC=CC=C1)C.ClCCl | 80 | 1 | CC(C)c1nc(C(=O)O)co1.NC1CC1>CN(C=O)C.C1(=CC=CC=C1)C.ClCCl>CC(C)c1nc(C(=O)NC2CC2)co1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6db241b1de6942798489126e4163fdde | CC(C)c1nc(C(=O)NC2CC2)co1.O=C=O>>CC(C)c1nc(C(=O)NC2CC2)c(C(=O)O)o1 | C(=O)=O.C(CCC)[Li].C1(CC1)NC(=O)C=1N=C(OC1)C(C)C>>C1(CC1)NC(=O)C=1N=C(OC1C(=O)O)C(C)C | [CH3:1][CH:2]([CH3:3])[c:4]1[n:5][c:6]([C:7](=[O:8])[NH:9][CH:10]2[CH2:11][CH2:12]2)[cH:13][o:17]1.[C:14](=[O:15])=[O:16]>>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][c:6]([C:7](=[O:8])[NH:9][CH:10]2[CH2:11][CH2:12]2)[c:13]([C:14](=[O:15])[OH:16])[o:17]1 | CC(C)c1nc(C(=O)NC2CC2)co1.O=C=O | CC(C)c1nc(C(=O)NC2CC2)c(C(=O)O)o1 | null | null | CCCCCC.O1CCCC1 | Acylation | OtherReaction | d7009895e441ce741d63fde0f10b8e58aef3dda277984d0da32c335724def808 | f2fa2063dd26da08ea200eb6cbb3037b91013a82352a2b60120e98f9e54cbd88 | O=C(NC1CC1)c1cocn1 | [C:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[#7;a:6]:[c:7](-[C:8]):[#8;a:9]:[cH;D2;+0:10]:1.[O;D1;H0:11]=[C;H0;D2;+0:12]=[O;H0;D1;+0:13]>>[C:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[#7;a:6]:[c:7](-[C:8]):[#8;a:9]:[c;H0;D3;+0:10]:1-[C;H0;D3;+0:12](=[O;D1;H0:11])-[OH;D1;+0:13] | 81 | [{"value": 81.0, "product": "C1(CC1)NC(=O)C=1N=C(OC1C(=O)O)C(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | At -70° C. and under a nitrogen blanket, 0.12 mol of n-butyllithium (80.0 ml of a 1.5 molar solution in hexane) was dripped into a solution of 10.4 g (0.054 mol) of 2-isopropyloxazole-4-carboxylic acid-cyclopropylamide in 250 ml of tetrahydrofuran, and the mixture was stirred for 30 minutes at this temperature. The rea... | 10.6084/m9.figshare.5104873.v1 | null | Carbon dioxide | Carboxylic acid | c1cocn1 | c1cocn1 | c1cocn1.C1CC1 | null | CCCCCC.O1CCCC1 | null | 0.5 | CC(C)c1nc(C(=O)NC2CC2)co1.O=C=O>CCCCCC.O1CCCC1>CC(C)c1nc(C(=O)NC2CC2)c(C(=O)O)o1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e8d6c976acfe418eb1c313ed305dfb2d | CC(C)(C)N.CCOC(=O)c1nc(SC)sc1C(=O)Cl>>CCOC(=O)c1nc(SC)sc1C(=O)NC(C)(C)C | C(C)OC(=O)C=1N=C(SC1C(=O)Cl)SC.C(C)(C)(C)N.Cl>>C(C)(C)(C)NC(=O)C1=C(N=C(S1)SC)C(=O)OCC | [NH2:15][C:16]([CH3:17])([CH3:18])[CH3:19].Cl[C:13]([c:12]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[n:7][c:8]([S:9][CH3:10])[s:11]1)=[O:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]([S:9][CH3:10])[s:11][c:12]1[C:13](=[O:14])[NH:15][C:16]([CH3:17])([CH3:18])[CH3:19] | CC(C)(C)N.CCOC(=O)c1nc(SC)sc1C(=O)Cl | CCOC(=O)c1nc(SC)sc1C(=O)NC(C)(C)C | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1cscn1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[C:8](-[#8:9])=[O;D1;H0:10].[C;D1;H3:11]-[C:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[NH2;D1;+0:15]>>[#8:9]-[C:8](=[O;D1;H0:10])-[c:7]1:[#7;a:6]:[c:5]:[#16;a:4]:[c:3]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:15]-[C:12](-[C;D1;H3:11])(-[C;D1;H3:13])-[C;D1;... | 100.2 | [{"value": 100.0, "product": "C(C)(C)(C)NC(=O)C1=C(N=C(S1)SC)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.2, "product": "C(C)(C)(C)NC(=O)C1=C(N=C(S1)SC)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | 3.50 g (13.2 mmol) of 4-ethoxycarbonyl-2-methylthiothiazole-5-carboxylic acid chloride was dissolved in 20 ml of dichloromethane and dripped, at 0° C., into a solution of 3.20 g (44 mmol) of tert-butylamine in 50 ml of dichloromethane. The mixture was allowed to warm up to room temperature and was then stirred for 14 h... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1cscn1 | HCl | ClCCl | null | 14 | CC(C)(C)N.CCOC(=O)c1nc(SC)sc1C(=O)Cl>ClCCl>CCOC(=O)c1nc(SC)sc1C(=O)NC(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2edd7bfaf0f643ea9042f3b3d6c043f5 | CCOC(=O)c1nc(SC)sc1C(=O)NC(C)(C)C>>CSc1nc(C(=O)O)c(C(=O)NC(C)(C)C)s1 | [OH-].[K+].C(C)(C)(C)NC(=O)C1=C(N=C(S1)SC)C(=O)OCC>>C(C)(C)(C)NC(=O)C1=C(N=C(S1)SC)C(=O)O | CC[O:8][C:6]([c:5]1[n:4][c:3]([S:2][CH3:1])[s:17][c:9]1[C:10](=[O:11])[NH:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:7]>>[CH3:1][S:2][c:3]1[n:4][c:5]([C:6](=[O:7])[OH:8])[c:9]([C:10](=[O:11])[NH:12][C:13]([CH3:14])([CH3:15])[CH3:16])[s:17]1 | CCOC(=O)c1nc(SC)sc1C(=O)NC(C)(C)C | CSc1nc(C(=O)O)c(C(=O)NC(C)(C)C)s1 | null | null | O.C(C)O.O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1cscn1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[#7;a:5]):[c:6]:[#16;a:7]>>[#16;a:7]:[c:6]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[#7;a:5] | null | [] | null | null | null | null | 0.82 g (14.6 mmol) of potassium hydroxide in 10 ml of water was added to a solution of 4.00 g (13.2 mmol) of 4-ethoxycarbonyl-2-methylthiothiazole-5-carboxylic acid-tert-butylamide in 50 ml of water/ethanol (2:1), and the mixture was refluxed for 2 hours. The solvent mixture was then removed under reduced pressure and ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cscn1 | Other | O.C(C)O.O | null | null | CCOC(=O)c1nc(SC)sc1C(=O)NC(C)(C)C>O.C(C)O.O>CSc1nc(C(=O)O)c(C(=O)NC(C)(C)C)s1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-918dffba71544237accb80156ad6bdb6 | C=O.CC(C)C[C@H](N)C(=O)O.CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)O>>CC(C)(C)OC(=O)N[C@@H](Cc1cc2ccccc2[nH]1)C(=O)O.CC(C)C[C@@H](C=O)NC(=O)OC(C)(C)C.CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)O | N([C@@H](CC(C)C)C(=O)O)C(=O)OC(C)(C)C.C=O.N[C@@H](CC(C)C)C(=O)O>>N([C@@H](CC(C)C)C(=O)O)C(=O)OC(C)(C)C.CC(C)(C)OC(=O)N[C@@H](CC1=CC=2C=CC=CC2N1)C(=O)O.N([C@@H](CC(C)C)C=O)C(=O)OC(C)(C)C | [O:5]=[CH2:6].[NH2:8][C@H:9]([C:20](=[O:21])[OH:22])[CH2:26][CH:24]([CH3:15])[CH3:25].[CH3:1][C:47]([CH3:2])([CH3:37])[O:46][C:44]([NH:43][C@@H:42]([CH2:41][CH:39]([CH3:38])[CH3:40])[C:51](=[O:52])[OH:53])=[O:45]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:10][c:11]1[cH:12][c:13]2[cH:14][cH:15]... | C=O.CC(C)C[C@H](N)C(=O)O.CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)O | CC(C)(C)OC(=O)N[C@@H](Cc1cc2ccccc2[nH]1)C(=O)O.CC(C)C[C@@H](C=O)NC(=O)OC(C)(C)C.CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2ffa72b2b656fefbc22f8e826b951442ec3c478a39284e3074cd512611ac0f4b | 8cbc1340892c80b218777bc6c951083673d7f43dbdc033f7e1a13d0cd1c5623b | c1ccc2[nH]ccc2c1 | [#7:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;H0;D4;+0:5](-[CH3;D1;+0:6])(-[CH3;D1;+0:7])-[CH3;D1;+0:8].[C;D1;H3:9]-[CH;D3;+0:10](-[CH3;D1;+0:11])-[CH2;D2;+0:12]-[C@H;D3;+0:13](-[NH2;D1;+0:14])-[C:15](=[O;D1;H0:16])-[O;D1;H1:17].[CH2;D1;+0:18]=[O;H0;D1;+0:19]>>[#7:20]-[C:21](-[C:22])-[CH2;D2;+0:12]-[CH;D3;+0:10](-[C;D1;H3:23])-... | null | [] | null | null | null | null | Leu-psi -Tpi-BHA resin is made by reacting Boc-Leu-psi -Trp-BHA resin with formaldehyde in accordance with the procedures as follows: Boc-Leu-psi -Trp-BHA resin is obtained from 1.0 g BHA resin (0.9 m mode NH2 g) with coupling Boc-Trp and Boc-Leu-CHO successively by the method indicated in Operation I and Operation II.... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Ether.Primary amine.Boc | Aldehyde.Carbamic ester.Carbamic ester.Ether.Ether.Ether.Boc.Boc.Boc | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | Other | null | null | null | C=O.CC(C)C[C@H](N)C(=O)O.CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)O>>CC(C)(C)OC(=O)N[C@@H](Cc1cc2ccccc2[nH]1)C(=O)O.CC(C)C[C@@H](C=O)NC(=O)OC(C)(C)C.CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-da46530a89434c3c8d249230d0da1142 | CCCC[C@H](NC(=O)OC(C)(C)C)C(=O)N1CCC[C@H]1C(N)=O>>CCCC[C@H](N)C(=O)N1CCC[C@H]1C(N)=O | C(C)(C)(C)OC(=O)N[C@@H](CCCC)C(=O)N1[C@H](C(=O)N)CCC1.Cl.O1CCOCC1>>Cl.N[C@@H](CCCC)C(=O)N1[C@H](C(=O)N)CCC1 | CC(C)(C)OC(=O)[NH:6][C@@H:5]([CH2:4][CH2:3][CH2:2][CH3:1])[C:7](=[O:8])[N:9]1[CH2:10][CH2:11][CH2:12][C@H:13]1[C:14]([NH2:15])=[O:16]>>[CH3:1][CH2:2][CH2:3][CH2:4][C@H:5]([NH2:6])[C:7](=[O:8])[N:9]1[CH2:10][CH2:11][CH2:12][C@H:13]1[C:14]([NH2:15])=[O:16] | CCCC[C@H](NC(=O)OC(C)(C)C)C(=O)N1CCC[C@H]1C(N)=O | CCCC[C@H](N)C(=O)N1CCC[C@H]1C(N)=O | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | C1CCNC1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6](-[C:7])-[C:8]-[C:9](-[N;D1;H2:10])=[O;D1;H0:11]>>[C:7]-[#7:6](-[C:4](=[O;D1;H0:5])-[C:2](-[C:3])-[NH2;D1;+0:1])-[C:8]-[C:9](-[N;D1;H2:10])=[O;D1;H0:11] | 95 | [{"value": 95.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | The N-tert-butyloxycarbonyl-L-norleucyl-proline amide (1 g, 3.05 mmol) was placed in a round bottom flask to which freshly prepared 4N HCl/dioxane (25 ml) was added. The solution was stirred for 1 hour. Evaporation of solvent in vacuo and then crystallization of an oily residue from methanol/ethyl ether gave the title ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1CC[NH]C1 | HO- | null | null | 1 | CCCC[C@H](NC(=O)OC(C)(C)C)C(=O)N1CCC[C@H]1C(N)=O>>CCCC[C@H](N)C(=O)N1CCC[C@H]1C(N)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0d244421dc454fa580394fccb09e3665 | Nc1ccccc1.O=C(Cl)c1cc2ccccc2s1>>O=C(Nc1ccccc1)c1cc2ccccc2s1 | S1C(=CC2=C1C=CC=C2)C(=O)Cl.NC1=CC=CC=C1.O>>S1C(=CC2=C1C=CC=C2)C(=O)NC2=CC=CC=C2 | [NH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1.Cl[C:2](=[O:1])[c:10]1[cH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[s:18]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[c:10]1[cH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[s:18]1 | Nc1ccccc1.O=C(Cl)c1cc2ccccc2s1 | O=C(Nc1ccccc1)c1cc2ccccc2s1 | null | null | C1(=CC=CC=C1)C | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccccc1)c1cc2ccccc2s1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:3](:[c:4]):[#16;a:5]:[c:6] | 77 | [{"value": 77.0, "product": "S1C(=CC2=C1C=CC=C2)C(=O)NC2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.6, "product": "S1C(=CC2=C1C=CC=C2)C(=O)NC2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 5 | HOUR | To 8 g (0.0407 mol) of benzothiophene-2-carboxylic acid chloride in 150 ml of toluene there are added with stirring at room temperature 7.6 g (0.0814 mol) of anilin, then, when the addition is complete, the mixture is stirred for 5 hours at 50° C., the reaction mixture is then poured into water, and precipitate which h... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2sccc2c1 | HCl | C1(=CC=CC=C1)C | 50 | 5 | Nc1ccccc1.O=C(Cl)c1cc2ccccc2s1>C1(=CC=CC=C1)C>O=C(Nc1ccccc1)c1cc2ccccc2s1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5496bc558f464336aaaccae32ef16785 | CC(=O)c1ccc([C@H]2C[C@@]3(C)[C@H](CC[C@]3(O)CC#C[Si](C)(C)C)[C@@H]3CCC4=CC(=O)CCC4=C32)cc1>>C#CC[C@@]1(O)CC[C@@H]2[C@@H]3CCC4=CC(=O)CCC4=C3[C@@H](c3ccc(C(C)=O)cc3)C[C@@]21C | C(C)(=O)C1=CC=C(C=C1)[C@@H]1C2=C3CCC(C=C3CC[C@H]2[C@H]2CC[C@@]([C@@]2(C)C1)(CC#C[Si](C)(C)C)O)=O.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>C(C)(=O)C1=CC=C(C=C1)[C@@H]1C2=C3CCC(C=C3CC[C@H]2[C@H]2CC[C@@]([C@@]2(C)C1)(CC#C)O)=O | C[Si](C)(C)[C:1]#[C:2][CH2:3][C@@:4]1([OH:5])[CH2:6][CH2:7][C@@H:8]2[C@@H:9]3[CH2:10][CH2:11][C:12]4=[CH:13][C:14](=[O:15])[CH2:16][CH2:17][C:18]4=[C:19]3[C@@H:20]([c:21]3[cH:22][cH:23][c:24]([C:25]([CH3:26])=[O:27])[cH:28][cH:29]3)[CH2:30][C@:31]12[CH3:32]>>[CH:1]#[C:2][CH2:3][C@@:4]1([OH:5])[CH2:6][CH2:7][C@@H:8]2[C@... | CC(=O)c1ccc([C@H]2C[C@@]3(C)[C@H](CC[C@]3(O)CC#C[Si](C)(C)C)[C@@H]3CCC4=CC(=O)CCC4=C32)cc1 | C#CC[C@@]1(O)CC[C@@H]2[C@@H]3CCC4=CC(=O)CCC4=C3[C@@H](c3ccc(C(C)=O)cc3)C[C@@]21C | null | null | O1CCCC1 | Deprotection | TMS deprotection from alkyne | e85676bb81da384790c9c858d44f182cdd01e3a79f77f7a239fe38487234cb96 | 56d526d7c9cb1bd7bee4940e216a9b1dd4597fd025a186b8d6e4675d8f4db26b | O=C1C=C2CC[C@@H]3C(=C2CC1)[C@@H](c1ccccc1)CC1CCC[C@@H]13 | C-[Si](-C)(-C)-[C;H0;D2;+0:1]#[C:2]-[C:3]>>[C:3]-[C:2]#[CH;D1;+0:1] | 69.6 | [{"value": 69.6, "product": "C(C)(=O)C1=CC=C(C=C1)[C@@H]1C2=C3CCC(C=C3CC[C@H]2[C@H]2CC[C@@]([C@@]2(C)C1)(CC#C)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | 470 mg of 11beta-(4-Acetylphenyl)-17alpha-hydroxy-17-(3-trimethysilyl-2-propinyl)-14beta-estra-4,9-dien-3-one in 24 ml of tetrahydrofuran is mixed with 2.35 ml of a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran and stirred for 5 minutes at room temperature. It is poured on water and extracted with ethyl... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne.Silyl protective group | Alkyne | null | null | c1ccccc1.C1=C2CC[C@@H]3C(=C2CCC1)CC[C@@H]1CCC[C@@H]13 | Other | O1CCCC1 | null | 0.083333 | CC(=O)c1ccc([C@H]2C[C@@]3(C)[C@H](CC[C@]3(O)CC#C[Si](C)(C)C)[C@@H]3CCC4=CC(=O)CCC4=C32)cc1>O1CCCC1>C#CC[C@@]1(O)CC[C@@H]2[C@@H]3CCC4=CC(=O)CCC4=C3[C@@H](c3ccc(C(C)=O)cc3)C[C@@]21C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7844a06e09664a17934167953fba756b | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cccnc1.Oc1ccc(Br)cc1>>Oc1ccc(-c2cccnc2)cc1 | BrC1=CC=C(C=C1)O.C(CCC)[Sn](C=1C=NC=CC1)(CCCC)CCCC>>N1=CC(=CC=C1)C1=CC=C(C=C1)O | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:6]1[cH:7][cH:8][cH:9][n:10][cH:11]1.Br[c:5]1[cH:4][cH:3][c:2]([OH:1])[cH:13][cH:12]1>>[OH:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][n:10][cH:11]2)[cH:12][cH:13]1 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cccnc1.Oc1ccc(Br)cc1 | Oc1ccc(-c2cccnc2)cc1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | O1CCOCC1 | C-C Coupling | Stille reaction_aryl | ce918bbb171f9e7bd99035931c043f0f33f636d165d8c0e73629d8717d6c595a | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1ccc(-c2cccnc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:6]1:[c:7]:[#7;a:8]:[c:9]:[c:10]:[c:11]:1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6]1:[c:7]:[#7;a:8]:[c:9]:[c:10]:[c:11]:1):[c:4]:[c:5] | 60 | [{"value": 60.0, "product": "N1=CC(=CC=C1)C1=CC=C(C=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 26.8 g of 4-bromophenol was taken under protective gas in 1000 ml of dioxane, mixed with 90 g 3-tributylstannylpyridine [preparation according to litt.: Org. Magn. Resonance, 7 (1975), 610] and 11.1 g of bis-(triphenylphosphine)-palladium(II) chloride and refluxed for 15 hours. After concentration by evaporation in a v... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccncc1.c1ccccc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | HBr.Sn | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.O1CCOCC1 | null | null | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cccnc1.Oc1ccc(Br)cc1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.O1CCOCC1>Oc1ccc(-c2cccnc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4aeb686c490442b0b6a3ee76700a4b23 | CN.COC(=O)c1ccnc(NCCCN2CCN(c3cccc(Cl)c3)CC2)n1>>CNC(=O)c1ccnc(NCCCN2CCN(c3cccc(Cl)c3)CC2)n1 | Cl.ClC=1C=C(C=CC1)N1CCN(CC1)CCCNC1=NC=CC(=N1)C(=O)OC.CO.CN>>Cl.ClC=1C=C(C=CC1)N1CCN(CC1)CCCNC1=NC=CC(=N1)C(=O)NC | [CH3:1][NH2:2].CO[C:3](=[O:4])[c:5]1[cH:6][cH:7][n:8][c:9]([NH:10][CH2:11][CH2:12][CH2:13][N:14]2[CH2:15][CH2:16][N:17]([c:18]3[cH:19][cH:20][cH:21][c:22]([Cl:23])[cH:24]3)[CH2:25][CH2:26]2)[n:27]1>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][n:8][c:9]([NH:10][CH2:11][CH2:12][CH2:13][N:14]2[CH2:15][CH2:16][N:17]([c:18... | CN.COC(=O)c1ccnc(NCCCN2CCN(c3cccc(Cl)c3)CC2)n1 | CNC(=O)c1ccnc(NCCCN2CCN(c3cccc(Cl)c3)CC2)n1 | null | null | CC(C)O | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1ccc(N2CCN(CCCNc3ncccn3)CC2)cc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[C;D1;H3:9]-[NH2;D1;+0:10]>>[C;D1;H3:9]-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1 | null | [] | null | null | null | null | 4.5 g (11.5 mmols) of methyl 2-[[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]amino]pyrimidine-4-carboxylate and 200 ml of methanol are introduced into a 0.5 l, round bottomed flask and then the solution is saturated with gaseous methylamine. The reaction mixture is stirred at room temperature while saturating several ti... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1cncnc1.C1C[NH]CC[NH]1.c1ccccc1 | HO- | CC(C)O | null | null | CN.COC(=O)c1ccnc(NCCCN2CCN(c3cccc(Cl)c3)CC2)n1>CC(C)O>CNC(=O)c1ccnc(NCCCN2CCN(c3cccc(Cl)c3)CC2)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-682b7c7c9d9d4c65b29faad31f704d69 | COC(=O)c1ccnc(NCCCN2CCN(c3cc(Cl)ccc3OC)CC2)n1.NCCNc1nc(=O)cc[nH]1>>COc1ccc(Cl)cc1N1CCN(CCCNc2nccc(C(=O)NCCNc3nc(=O)cc[nH]3)n2)CC1 | ClC=1C=CC(=C(C1)N1CCN(CC1)CCCNC1=NC=CC(=N1)C(=O)OC)OC.NCCNC=1NC=CC(N1)=O>>ClC=1C=CC(=C(C1)N1CCN(CC1)CCCNC1=NC=CC(=N1)C(=O)NCCNC=1NC=CC(N1)=O)OC | CO[C:23]([c:22]1[cH:21][cH:20][n:19][c:18]([NH:17][CH2:16][CH2:15][CH2:14][N:13]2[CH2:12][CH2:11][N:10]([c:9]3[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([Cl:7])[cH:8]3)[CH2:38][CH2:37]2)[n:36]1)=[O:24].[NH2:25][CH2:26][CH2:27][NH:28][c:29]1[n:30][c:31](=[O:32])[cH:33][cH:34][nH:35]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Cl:7... | COC(=O)c1ccnc(NCCCN2CCN(c3cc(Cl)ccc3OC)CC2)n1.NCCNc1nc(=O)cc[nH]1 | COc1ccc(Cl)cc1N1CCN(CCCNc2nccc(C(=O)NCCNc3nc(=O)cc[nH]3)n2)CC1 | null | null | C(CCC)O | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | O=C(NCCNc1nc(=O)cc[nH]1)c1ccnc(NCCCN2CCN(c3ccccc3)CC2)n1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1 | null | [] | null | null | null | null | 1.89 g of (4.5 mmols) of methyl 2-[[3-[4-(5-chloro-2-methoxyphenyl)piperazin-1-yl]propyl]amino]-pyrimidine-4-carboxylate and 0.77 g (5 mmols) of 2-[(2-aminoethyl)amino]pyrimidin-4(1H)-one in 5 ml of n-butanol are introduced into a 25 ml, round bottomed flask. The mixture is heated at the reflux temperature of the solve... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1cncnc1.c1ccncn1 | HO- | C(CCC)O | null | null | COC(=O)c1ccnc(NCCCN2CCN(c3cc(Cl)ccc3OC)CC2)n1.NCCNc1nc(=O)cc[nH]1>C(CCC)O>COc1ccc(Cl)cc1N1CCN(CCCNc2nccc(C(=O)NCCNc3nc(=O)cc[nH]3)n2)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-61c8410b006347f6bdbec94f311bc8c4 | COC(=O)c1ccnc(NCCN2CCN(c3cc(Cl)ccc3OC)CC2)n1.NCCCNc1nc(=O)cc[nH]1>>COc1ccc(Cl)cc1N1CCN(CCNc2nccc(C(=O)NCCCNc3nc(=O)cc[nH]3)n2)CC1 | ClC=1C=CC(=C(C1)N1CCN(CC1)CCNC1=NC=CC(=N1)C(=O)OC)OC.NCCCNC=1NC=CC(N1)=O>>ClC=1C=CC(=C(C1)N1CCN(CC1)CCNC1=NC=CC(=N1)C(=O)NCCCNC=1NC=CC(N1)=O)OC | CO[C:22]([c:21]1[cH:20][cH:19][n:18][c:17]([NH:16][CH2:15][CH2:14][N:13]2[CH2:12][CH2:11][N:10]([c:9]3[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([Cl:7])[cH:8]3)[CH2:38][CH2:37]2)[n:36]1)=[O:23].[NH2:24][CH2:25][CH2:26][CH2:27][NH:28][c:29]1[n:30][c:31](=[O:32])[cH:33][cH:34][nH:35]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Cl:7... | COC(=O)c1ccnc(NCCN2CCN(c3cc(Cl)ccc3OC)CC2)n1.NCCCNc1nc(=O)cc[nH]1 | COc1ccc(Cl)cc1N1CCN(CCNc2nccc(C(=O)NCCCNc3nc(=O)cc[nH]3)n2)CC1 | null | null | C(CCC)O | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | O=C(NCCCNc1nc(=O)cc[nH]1)c1ccnc(NCCN2CCN(c3ccccc3)CC2)n1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1 | null | [] | null | null | null | null | 3.0 g (7.4 mmols) of methyl 2-[[2-[4-(5-chloro-2-methoxyphenyl)piperazin- 1-yl]ethyl]amino]-pyrimidine-4-carboxylate and 1.5 g (8.9 mmols) of 2-[(3-aminopropyl)amino]pyrimidin-4(1H)-one in 20 ml of n-butanol are introduced into a 100 ml, round bottomed flask. The mixture is heated at the reflux temperature of the solve... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1cncnc1.c1ccncn1 | HO- | C(CCC)O | null | null | COC(=O)c1ccnc(NCCN2CCN(c3cc(Cl)ccc3OC)CC2)n1.NCCCNc1nc(=O)cc[nH]1>C(CCC)O>COc1ccc(Cl)cc1N1CCN(CCNc2nccc(C(=O)NCCCNc3nc(=O)cc[nH]3)n2)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d740cb40c09548b39dbf951d10f89106 | COc1ccc(Cl)cc1N1CCN(CCNc2nccc(C(=O)N3CCC(N)CC3)n2)CC1.CSc1nc(=O)cc[nH]1>>COc1ccc(Cl)cc1N1CCN(CCNc2nccc(C(=O)N3CCC(Nc4nc(=O)cc[nH]4)CC3)n2)CC1 | ClC=1C=CC(=C(C1)N1CCN(CC1)CCNC1=NC=CC(=N1)C(=O)N1CCC(CC1)N)OC.CSC=1NC=CC(N1)=O>>ClC=1C=CC(=C(C1)N1CCN(CC1)CCNC1=NC=CC(=N1)C(=O)N1CCC(CC1)NC=1NC=CC(N1)=O)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Cl:7])[cH:8][c:9]1[N:10]1[CH2:11][CH2:12][N:13]([CH2:14][CH2:15][NH:16][c:17]2[n:18][cH:19][cH:20][c:21]([C:22](=[O:23])[N:24]3[CH2:25][CH2:26][CH:27]([NH2:28])[CH2:36][CH2:37]3)[n:38]2)[CH2:39][CH2:40]1.CS[c:29]1[n:30][c:31](=[O:32])[cH:33][cH:34][nH:35]1>>[CH3:1][O:2][c:3]1[cH:4][... | COc1ccc(Cl)cc1N1CCN(CCNc2nccc(C(=O)N3CCC(N)CC3)n2)CC1.CSc1nc(=O)cc[nH]1 | COc1ccc(Cl)cc1N1CCN(CCNc2nccc(C(=O)N3CCC(Nc4nc(=O)cc[nH]4)CC3)n2)CC1 | null | null | C1(=CC(=CC=C1)C)C | Heteroatom Alkylation and Arylation | OtherReaction | 5f2ea2586cfa2f11d765b05bd73f877d3eba93e8a380c059f41d4627fde15d79 | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | O=C(c1ccnc(NCCN2CCN(c3ccccc3)CC2)n1)N1CCC(Nc2nc(=O)cc[nH]2)CC1 | C-S-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7](-[NH2;D1;+0:8])-[C:9]>>[C:6]-[C:7](-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5])-[C:9] | 55.9 | [{"value": 55.9, "product": "ClC=1C=CC(=C(C1)N1CCN(CC1)CCNC1=NC=CC(=N1)C(=O)N1CCC(CC1)NC=1NC=CC(N1)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2.3 g (4.9 mmol) of 1-[2-[[2-[4-(5-chloro-2-methoxyphenyl)piperazin-1-yl]ethyl]amino]pyrimidin-4-ylcarbonyl]piperidin-4-amine, and 0.9 g (6.3 mmols) of 2-methylthiopyrimidin-4(1H)-one in solution in 40 ml of m-xylene are introduced into a 0.5 l, round bottomed flask and the mixture is heated at reflux of the m-xylene f... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | c1ccncn1 | c1ccncn1 | c1ccccc1.C1C[NH]CC[NH]1.c1cncnc1.C1CC[NH]CC1.c1ccncn1 | Other | C1(=CC(=CC=C1)C)C | null | null | COc1ccc(Cl)cc1N1CCN(CCNc2nccc(C(=O)N3CCC(N)CC3)n2)CC1.CSc1nc(=O)cc[nH]1>C1(=CC(=CC=C1)C)C>COc1ccc(Cl)cc1N1CCN(CCNc2nccc(C(=O)N3CCC(Nc4nc(=O)cc[nH]4)CC3)n2)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-29b1539b5e8e4303be8267bfa4999d0d | CCOC(=O)C(=O)OCC.COc1ccc(Br)c(C(C)C(=O)[O-])c1>>CCOC(=O)C(=O)C(Cc1cc(OC)ccc1Br)C(=O)OCC | O.CC(C)([O-])C.[K+].BrC1=C(C=C(C=C1)OC)C(C(=O)[O-])C.C(C(=O)OCC)(=O)OCC.CCOCC.CCOCC>>O=C(C(=O)OCC)C(CC1=C(C=CC(=C1)OC)Br)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[O:21][CH2:22][CH3:23].[O-][C:19]([CH:8]([CH3:9])[c:10]1[cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16][c:17]1[Br:18])=[O:20]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[CH:8]([CH2:9][c:10]1[cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16][c:17]1[Br:18])[C:19](=[O:20])[O:21][CH2:22... | CCOC(=O)C(=O)OCC.COc1ccc(Br)c(C(C)C(=O)[O-])c1 | CCOC(=O)C(=O)C(Cc1cc(OC)ccc1Br)C(=O)OCC | null | null | null | C-C Coupling | OtherReaction | a5d192f9fabd52ac26c08069b9ccd9bdf3bf887257f96bffa9fa72c098f21d83 | d4410d30228c25b48f58ac92bab260611786b9e684966602ec75966220b57fba | c1ccccc1 | [Br;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[CH;D3;+0:5](-[CH3;D1;+0:6])-[C;H0;D3;+0:7](-[O-])=[O;D1;H0:8]):[c:9]:[c:10].[C:11]-[#8:12]-[C:13](=[O;D1;H0:14])-[C;H0;D3;+0:15](=[O;D1;H0:16])-[O;H0;D2;+0:17]-[C:18]-[C;D1;H3:19]>>[Br;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[CH2;D2;+0:6]-[CH;D3;+0:5](-[C;H0;D3;+0:7](=[O;D1;H0... | 90 | [{"value": 90.0, "product": "O=C(C(=O)OCC)C(CC1=C(C=CC(=C1)OC)Br)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | Potassium t-butoxide (6.72 g) was suspended in 30 ml of anhydrous ether and cooled to 0° C. A solution of 14.35 g of ethyl 3-(2-bromo-5-methoxyphenyl-propionate and 10.95 g diethyl oxalate in 10 ml ether was added dropwise over 15 min. After 2 at 25° C., the reaction was poured into 100 ml H2O and the aqueous layer was... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ketone.Ester.Ester | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | 0 | null | CCOC(=O)C(=O)OCC.COc1ccc(Br)c(C(C)C(=O)[O-])c1>>CCOC(=O)C(=O)C(Cc1cc(OC)ccc1Br)C(=O)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-09ecf8fbcf7143b4b4b1bb485c9c30d9 | CCOC(=O)C1=C(C(=O)OCC)c2c(OC)ccc(Br)c2C1>>CCOC(=O)C1Cc2cccc(OC)c2C1C(=O)OCC | BrC=1C=CC(=C2C(=C(CC12)C(=O)OCC)C(=O)OCC)OC>>COC1=C2C(C(CC2=CC=C1)C(=O)OCC)C(=O)OCC | Br[c:9]1[c:8]2[c:15]([c:12]([O:13][CH3:14])[cH:11][cH:10]1)[C:16]([C:17](=[O:18])[O:19][CH2:20][CH3:21])=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7]2>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][c:8]2[cH:9][cH:10][cH:11][c:12]([O:13][CH3:14])[c:15]2[CH:16]1[C:17](=[O:18])[O:19][CH2:20][CH3:21] | CCOC(=O)C1=C(C(=O)OCC)c2c(OC)ccc(Br)c2C1 | CCOC(=O)C1Cc2cccc(OC)c2C1C(=O)OCC | null | [Pd].[O-]S(=O)(=O)[O-].[Ba+2] | C(C)O | Reduction | OtherReaction | 00ee50f454e9483f7fd1bf0416428eb028e8c793c0f9d9e39b946a0cad0350d0 | 3b66793f09edb4afa775171d5142cfc257af0edb413721d00ecd4602c93c6b9e | c1ccc2c(c1)CCC2 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[c:6]:1-[C:7]-[C;H0;D3;+0:8](-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12])=[C;H0;D3;+0:13]-2-[C:14](=[O;D1;H0:15])-[#8:16]-[C:17]>>[C:17]-[#8:16]-[C:14](=[O;D1;H0:15])-[CH;D3;+0:13]1-[CH;D3;+0:8](-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12])-[C:7]-[c:6]2:[cH;D2;+0:1]:[c:2]:[c:3]:[c:4]:[c:5]:... | 96.9 | [{"value": 96.9, "product": "COC1=C2C(C(CC2=CC=C1)C(=O)OCC)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The diester from Example 2 (19.39 g) was dissolved in 250 ml ethanol. To the solution was added 5.20 g of 10% Pd/BaSO4 and 7.15 g NaOAc.3H2O. The reaction was hydrogenated at 4 atm pressure. The catalyst was filtered and the solvent evaporated. The product was dissolved in ether, washed with 5% NaHCO3, dried (MgSO4), a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ester | Ester.Ester | C1=Cc2ccccc2C1 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | Br- | [Pd].[O-]S(=O)(=O)[O-].[Ba+2].C(C)O | null | null | CCOC(=O)C1=C(C(=O)OCC)c2c(OC)ccc(Br)c2C1>[Pd].[O-]S(=O)(=O)[O-].[Ba+2].C(C)O>CCOC(=O)C1Cc2cccc(OC)c2C1C(=O)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7fb126bc875649eb8713b2431fdb30fa | COC1c2ccccc2C2CN(Cc3ccccc3)CC21>>COC1c2ccccc2C2CNCC21 | Cl.C(C1=CC=CC=C1)N1CC2C(C1)C(C=1C=CC=CC12)OC>>Cl.COC1C=2C=CC=CC2C2CNCC21 | c1ccc(C[N:12]2[CH2:11][CH:10]3[c:9]4[c:4]([cH:5][cH:6][cH:7][cH:8]4)[CH:3]([O:2][CH3:1])[CH:14]3[CH2:13]2)cc1>>[CH3:1][O:2][CH:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[CH:10]2[CH2:11][NH:12][CH2:13][CH:14]12 | COC1c2ccccc2C2CN(Cc3ccccc3)CC21 | COC1c2ccccc2C2CNCC21 | null | [Pd] | CO | Deprotection | Hydrogenolysis of tertiary amines | dd42f97580a8f7f0cafefbd81bcf5a8bcbf7040d74f9339d074d65acb45f1646 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1ccc2c(c1)CC1CNCC21 | C(-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1)-c1:c:c:c:c:c:1>>[C:3]1-[C:2]-[NH;D2;+0:1]-[C:5]-[C:4]-1 | 90.5 | [{"value": 90.5, "product": "Cl.COC1C=2C=CC=CC2C2CNCC21", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The product from Example 5 (4.90 g) was hydrogenated with 2.45 g 20% Pd/C in 200 ml methanol at 3 atm, affording 3.17 g of the desired product, mp: 208°-209° C. NMR (d6DMSO/D2O) δ2.83 (m, 2H), 3.14-3.29 (m, 3H), 3.46 (dd, 1H), 3.55 (dd, 1H), 3.80 (s, 3H), 3.95 (m, 1H), 6.85 (d, 2H), 7.25 (t, 1H).
Conditions: See reacti... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.c1ccc2c(c1)CC1C[NH]CC21 | c1ccc2c(c1)CC1CNCC21 | c1ccc2c(c1)CC1CNCC21 | Other | [Pd].CO | null | null | COC1c2ccccc2C2CN(Cc3ccccc3)CC21>[Pd].CO>COC1c2ccccc2C2CNCC21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-fb02e62a59a44836a806f3943ed12dcc | BrB(Br)Br.CCCN1CC2c3ccccc3C(OC)C2C1>>Br.CCCN1CC2c3ccccc3C(O)C2C1 | Cl.COC1C=2C=CC=CC2C2CN(CC21)CCC.B(Br)(Br)Br>>Br.OC1C=2C=CC=CC2C2CN(CC21)CCC | BrB(Br)[Br:1].C[O:15][CH:14]1[c:13]2[c:8]([cH:9][cH:10][cH:11][cH:12]2)[CH:7]2[CH2:6][N:5]([CH2:4][CH2:3][CH3:2])[CH2:17][CH:16]21>>[BrH:1].[CH3:2][CH2:3][CH2:4][N:5]1[CH2:6][CH:7]2[c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[CH:14]([OH:15])[CH:16]2[CH2:17]1 | BrB(Br)Br.CCCN1CC2c3ccccc3C(OC)C2C1 | Br.CCCN1CC2c3ccccc3C(O)C2C1 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 033263114fa374bfee35f27920670e8f6275414faa199071efed4247f43e41f8 | 816a42e4e92b4becc10e09218671f2e2a7942c9348b22e40d965e6444e589265 | c1ccc2c(c1)CC1CNCC21 | Br-B(-Br)-[Br;H0;D1;+0:1].C-[O;H0;D2;+0:2]-[C:3](-[C:4])-[c:5]>>[BrH;D0;+0:1].[C:4]-[C:3](-[OH;D1;+0:2])-[c:5] | null | [] | -78 | CELSIUS | null | null | The product from Example 9 (0.490 g) was dissolved in 25 ml methylene chloride and cooled to -78° C. To the reaction was added 0.69 ml BBr3. The reaction was warmed to 0° C. for 4 h and then cooled to -78° C. The reaction was quenched by the addition of 5 ml methanol and the solvent was evaporated. The resulting solid ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Secondary alcohol | null | null | c1ccc2c(c1)CC1C[NH]CC21 | HBr.B | C(Cl)Cl | -78 | null | BrB(Br)Br.CCCN1CC2c3ccccc3C(OC)C2C1>C(Cl)Cl>Br.CCCN1CC2c3ccccc3C(O)C2C1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b8624136abe04640a5b5ceda72784b10 | COC1c2ccccc2C2CN(CC#N)CC21>>COC1c2ccccc2C2CN(CCN)CC21 | COC1C=2C=CC=CC2C2CN(CC21)CC#N>>COC1C=2C=CC=CC2C2CN(CC21)CCN | [CH3:1][O:2][CH:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[CH:10]2[CH2:11][N:12]([CH2:13][C:14]#[N:15])[CH2:16][CH:17]12>>[CH3:1][O:2][CH:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[CH:10]2[CH2:11][N:12]([CH2:13][CH2:14][NH2:15])[CH2:16][CH:17]12 | COC1c2ccccc2C2CN(CC#N)CC21 | COC1c2ccccc2C2CN(CCN)CC21 | null | [Rh] | CO.N | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccc2c(c1)CC1CNCC21 | [#7:1]-[C:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4]>>[#7:1]-[C:2]-[CH2;D2;+0:3]-[NH2;D1;+0:4] | 95.3 | [{"value": 95.3, "product": "COC1C=2C=CC=CC2C2CN(CC21)CCN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | The product from Example 16 (1.00 g) was dissolved in 90 ml methanol and 10 ml anhydrous ammonia. 0.100 g 5% Rh/Al2O3 was added and the reaction was hydrogenated at 4 atm for 4 h. The reaction was filtered and the solvent removed to yield 0.97 g of the desired product as a colorless oil. NMR (CDCl3) δ2.20-2.61 (m, 3H),... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccc2c(c1)CC1C[NH]CC21 | null | [Rh].CO.N | null | 4 | COC1c2ccccc2C2CN(CC#N)CC21>[Rh].CO.N>COC1c2ccccc2C2CN(CCN)CC21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f54e63fe817945f5aca1b6509ef67a57 | COC1c2ccccc2C2CN(CCN)CC21.O=C(Cl)c1ccc(F)cc1>>COC1c2ccccc2C2CN(CCNC(=O)c3ccc(F)cc3)CC21.Cl | COC1C=2C=CC=CC2C2CN(CC21)CCN.FC1=CC=C(C(=O)Cl)C=C1>>Cl.COC1C=2C=CC=CC2C2CN(CC21)CCNC(C2=CC=C(C=C2)F)=O | [CH3:1][O:2][CH:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[CH:10]2[CH2:11][N:12]([CH2:13][CH2:14][NH2:15])[CH2:25][CH:26]12.[C:16](=[O:17])([c:18]1[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]1)[Cl:27]>>[CH3:1][O:2][CH:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[CH:10]2[CH2:11][N:12]([CH2:13][CH2:14][NH:15][C:16](=[O:17])[c:18]3... | COC1c2ccccc2C2CN(CCN)CC21.O=C(Cl)c1ccc(F)cc1 | COC1c2ccccc2C2CN(CCNC(=O)c3ccc(F)cc3)CC21.Cl | null | null | C(Cl)Cl.C(C)N(CC)CC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCN1CC2Cc3ccccc3C2C1)c1ccccc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[Cl;H0;D1;+0:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c:7](:[c:8]):[c:9].[ClH;D0;+0:4] | null | [] | -20 | CELSIUS | 30 | MINUTE | The product from Example 17 (0.95 g) was dissolved in 50 ml methylene chloride and 1.5 ml triethyl amine. The solution was cooled to -20° C. and 0.59 ml p-fluorobenzoyl chloride was added. After 30 min, the reaction was quenched in 5% NaHCO3 and extracted with ethyl acetate. The organic extracts were dried (Na2SO4), ev... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c(c1)CC1C[NH]CC21.c1ccccc1 | null | C(Cl)Cl.C(C)N(CC)CC | -20 | 0.5 | COC1c2ccccc2C2CN(CCN)CC21.O=C(Cl)c1ccc(F)cc1>C(Cl)Cl.C(C)N(CC)CC>COC1c2ccccc2C2CN(CCNC(=O)c3ccc(F)cc3)CC21.Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0c78cd059b394bef950f6b265b6865dc | CCOC(OCC)OCC.COc1ccc(Br)c2c1C(=O)CC2>>CCOC(OCC)C1Cc2c(Br)ccc(OC)c2C1=O | C(C)(C)N(CC)C(C)C.C(OCC)(OCC)OCC.BrC1=C2CCC(C2=C(C=C1)OC)=O.B(F)(F)F.CCOCC>>C(C)OC(C1C(C2=C(C=CC(=C2C1)Br)OC)=O)OCC | CCO[CH:4]([O:3][CH2:2][CH3:1])[O:5][CH2:6][CH3:7].[CH2:8]1[CH2:9][c:10]2[c:11]([Br:12])[cH:13][cH:14][c:15]([O:16][CH3:17])[c:18]2[C:19]1=[O:20]>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[CH:8]1[CH2:9][c:10]2[c:11]([Br:12])[cH:13][cH:14][c:15]([O:16][CH3:17])[c:18]2[C:19]1=[O:20] | CCOC(OCC)OCC.COc1ccc(Br)c2c1C(=O)CC2 | CCOC(OCC)C1Cc2c(Br)ccc(OC)c2C1=O | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | 0ccb5acbe1cc0192cb1d36afc7997fa48bf65148c2d46ad3b88a4f6cb2d2f99e | 155bcdfe4c4a838582eb097f30902e58c733d6d3e0c4634faa32630a07995baa | O=C1CCc2ccccc21 | C-C-O-[CH;D3;+0:1](-[#8:2]-[C:3])-[#8:4]-[C:5].[O;D1;H0:6]=[C:7]1-[CH2;D2;+0:8]-[C:9]-[c:10]:[c:11]-1>>[C:3]-[#8:2]-[CH;D3;+0:1](-[#8:4]-[C:5])-[CH;D3;+0:8]1-[C:9]-[c:10]:[c:11]-[C:7]-1=[O;D1;H0:6] | null | [] | 0 | CELSIUS | null | null | Triethyl orthoformate (16.5 ml) was cooled to -30° C. and 15.0 ml BF3.Et2O in 50 ml methylene chloride was added. The reaction was warmed to 0° C. for 15 min, and then cooled to -78° C. To the reaction was added 12.05 g of the product from Example 34 in 50 ml methylene chloride, followed by dropwise addition of 19.4 ml... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Ether.Ether | Ketone.Ether.Ether | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | HO- | C(Cl)Cl | 0 | null | CCOC(OCC)OCC.COc1ccc(Br)c2c1C(=O)CC2>C(Cl)Cl>CCOC(OCC)C1Cc2c(Br)ccc(OC)c2C1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-75841078706c471fb11a460ffbd5dc91 | COc1cccc2c1[C@H]1CCN(Cc3ccccc3)C[C@H]1C2>>COc1cccc2c1[C@H]1CCNC[C@H]1C2 | Cl.C(C1=CC=CC=C1)N1C[C@@H]2[C@H](CC1)C=1C(=CC=CC1C2)OC>>Cl.COC1=CC=CC=2C[C@@H]3CNCC[C@@H]3C12 | c1ccc(C[N:12]2[CH2:11][CH2:10][C@@H:9]3[c:8]4[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][c:7]4[CH2:15][C@@H:14]3[CH2:13]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[C@H:9]1[CH2:10][CH2:11][NH:12][CH2:13][C@H:14]1[CH2:15]2 | COc1cccc2c1[C@H]1CCN(Cc3ccccc3)C[C@H]1C2 | COc1cccc2c1[C@H]1CCNC[C@H]1C2 | null | [Pd] | CO | Deprotection | Hydrogenolysis of tertiary amines | 3b656f8cdadf0ccb010defa73ceaa399d59e9f35c9cde9dd97ae13bfab1c0834 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1ccc2c(c1)C[C@@H]1CNCC[C@H]21 | [C:1]-[C:2]-[N;H0;D3;+0:3](-C-c1:c:c:c:c:c:1)-[C:4]-[C:5]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C:5] | 82.6 | [{"value": 82.6, "product": "Cl.COC1=CC=CC=2C[C@@H]3CNCC[C@@H]3C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The product from Example 41 (1.80 g) was combined with 0.90 g 20% Pd/C in 100 ml methanol and evaporated to yield 1.08 g of the desired product as a white solid, mp: 140°-3° C. NMR (d6DMSO) δ 1.70 (m, 1H), 2.02 (m, 1H), 2.60 (m, 1H), 2.78-3.30 (m, 7H), 3.77 (s, 3H), 6.80 (d, 1H), 6.84 (d, 1H), 7.15 (t, 1H).
Conditions:... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.c1ccc2c(c1)C[C@@H]1C[NH]CC[C@H]21 | c1ccc2c(c1)C[C@@H]1CNCC[C@H]21 | c1ccc2c(c1)C[C@@H]1CNCC[C@H]21 | Other | [Pd].CO | null | null | COc1cccc2c1[C@H]1CCN(Cc3ccccc3)C[C@H]1C2>[Pd].CO>COc1cccc2c1[C@H]1CCNC[C@H]1C2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-cc146a0b13854115a3294a70fa64f354 | COc1ccc(Br)c2c1C(C#N)C(C#N)CC2>>COc1cccc2c1C(C#N)C(C#N)CC2 | BrC1=C2CCC(C(C2=C(C=C1)OC)C#N)C#N.CC(=O)[O-].[Na+]>>COC=1C=CC=C2CCC(C(C12)C#N)C#N | Br[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:8]2[c:7]1[CH2:16][CH2:15][CH:12]([C:13]#[N:14])[CH:9]2[C:10]#[N:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[CH:9]([C:10]#[N:11])[CH:12]([C:13]#[N:14])[CH2:15][CH2:16]2 | COc1ccc(Br)c2c1C(C#N)C(C#N)CC2 | COc1cccc2c1C(C#N)C(C#N)CC2 | null | [Pd].[O-]S(=O)(=O)[O-].[Ba+2] | CO | Functional Group Interconversion | Aromatic dehalogenation | 94addc37b1234c3916ac52b9db2a134e35734d066e92c9df0d41a10d4be2c2b1 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccc2c(c1)CCCC2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5])-[C:6]>>[C:6]-[c:4](:[c:5]):[cH;D2;+0:1]:[c:2]:[c:3] | 85.1 | [{"value": 85.1, "product": "COC=1C=CC=C2CCC(C(C12)C#N)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The product from Example 53 (2.90 g) was treated with 3.0 g 10% Pd/BaSO4 and 1.36 g NaOAc in 250 ml methanol and hydrogenated at 4 atm for 4 h. The reaction was filtered and evaporated; and the product was dissolved in ethyl acetate, washed with 5% NaHCO3, dried (MgSO4), and evaporated to yield 1.80 g of the desired pr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | Br- | [Pd].[O-]S(=O)(=O)[O-].[Ba+2].CO | null | null | COc1ccc(Br)c2c1C(C#N)C(C#N)CC2>[Pd].[O-]S(=O)(=O)[O-].[Ba+2].CO>COc1cccc2c1C(C#N)C(C#N)CC2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-623055db120040d483ebba9a6496e49a | CCOC(=O)C(=O)OCC.CCOC(=O)CCCc1cc(OC)ccc1Br>>CCOC(=O)C(=O)C(CCc1cc(OC)ccc1Br)C(=O)OCC | O.CC(C)([O-])C.[K+].C(C)OC(CCCC1=C(C=CC(=C1)OC)Br)=O.C(C(=O)OCC)(=O)OCC>>C(C)OC(C(C(CCC1=C(C=CC(=C1)OC)Br)C(=O)OCC)=O)=O | CCO[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[O:7].[CH2:8]([CH2:9][CH2:10][c:11]1[cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17][c:18]1[Br:19])[C:20](=[O:21])[O:22][CH2:23][CH3:24]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[CH:8]([CH2:9][CH2:10][c:11]1[cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17][c:18]1[Br:19])[C:20](=[O:2... | CCOC(=O)C(=O)OCC.CCOC(=O)CCCc1cc(OC)ccc1Br | CCOC(=O)C(=O)C(CCc1cc(OC)ccc1Br)C(=O)OCC | null | null | CCOCC | C-C Coupling | OtherReaction | 831b39d9ccf68cb6d272eab2c65f66125e8f825272f7523cabe1d45c78ab2fbb | d0be73e10992279cb1102524f458cbe914ec5b996a4c52f764855ef41c8e23eb | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[C:7]-[C:8]-[CH2;D2;+0:9]-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13]>>[C:7]-[C:8]-[CH;D3;+0:9](-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6] | 89 | [{"value": 89.0, "product": "C(C)OC(C(C(CCC1=C(C=CC(=C1)OC)Br)C(=O)OCC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.8, "product": "C(C)OC(C(C(CCC1=C(C=CC(=C1)OC)Br)C(=O)OCC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | Potassium t-butoxide (26.94 g) was suspended in 130 ml of anhydrous ether and cooled to 0° C. A solution of 60.24 g ethyl -4-(2-bromo-5-methoxy phenyl)butyrate and 43.84 g diethyl oxalate in 60 ml ether was added dropwise over 20 min. After 2 h at 25° C., the reaction was poured into 400 ml H2O and the aqueous layer wa... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester | Ketone | null | null | c1ccccc1 | HO- | CCOCC | 0 | 2 | CCOC(=O)C(=O)OCC.CCOC(=O)CCCc1cc(OC)ccc1Br>CCOCC>CCOC(=O)C(=O)C(CCc1cc(OC)ccc1Br)C(=O)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1b12255dade444fbb86d1602f50259b7 | CN(C)C=O.COC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)OC(C)(C)C>>COCCOCc1cc(O)ccc1C[C@@H](CO)NC(=O)OC(C)(C)C | COC([C@@H](NC(=O)OC(C)(C)C)CC1=CC=C(C=C1)O)=O.[H-].[Na+].[Cl-].[Li+].[BH4-].[Na+].CN(C=O)C>>C(C)(C)(C)OC(=O)N[C@@H](CC1=C(C=C(C=C1)O)COCCOC)CO | N([CH3:3])([CH3:4])[CH:6]=[O:5].[CH3:1][O:2][C:16]([C@H:15]([CH2:14][c:13]1[cH:7][cH:8][c:9]([OH:10])[cH:11][cH:12]1)[NH:18][C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:17]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][c:7]1[cH:8][c:9]([OH:10])[cH:11][cH:12][c:13]1[CH2:14][C@@H:15]([CH2:16][OH:17])[NH:18][C:19... | CN(C)C=O.COC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)OC(C)(C)C | COCCOCc1cc(O)ccc1C[C@@H](CO)NC(=O)OC(C)(C)C | null | null | C(C)O.O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 00d452f033d2acdebf3ac4c04c76e70023edc8026121ba0d8470b5f4d221eced | 4ce9596af059d87d7f691a50ccc0b4745b9b3eeabaf308152f422c9f89fd584c | c1ccccc1 | [C;D1;H3:1]-[O;H0;D2;+0:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5](-[#7:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C;D1;H3:13])-[C:14]-[c:15](:[c:16]):[cH;D2;+0:17]:[c:18]:[c:19].[CH3;D1;+0:20]-N(-[CH3;D1;+0:21])-[CH;D2;+0:22]=[O;H0;D1;+0:23]>>[C;D1;H3:1]-[O;H0;D2;+0:2]-[CH2;D2;+0:20]-[CH2;D2;+0:... | null | [] | null | null | null | null | 13.39 g of N-t-butoxycarbonyltyrosine methyl ester was dissolved in 65 ml of tetrahydrofuran and 65 ml of dimethylformamide. 1.9 g of 60% sodium hydride was added to the solution under stirring while ice-cooled. After the ice bath was removed, the mixture was stirred at room temperature for 30 minutes and then 5.4 g of... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Tertiary amide | Ether.Ether.Primary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | C(C)O.O1CCCC1 | null | null | CN(C)C=O.COC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)OC(C)(C)C>C(C)O.O1CCCC1>COCCOCc1cc(O)ccc1C[C@@H](CO)NC(=O)OC(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e4a23dd9d11840d1854afd3d74c6084e | CCOC(=O)c1c(S(C)=O)sc2ccccc2c1=O>>CCOC(=O)c1c(S)sc2ccccc2c1=O | C(C)OC(=O)C1=C(SC2=C(C1=O)C=CC=C2)S(=O)C.S.[Na]>>C(C)OC(=O)C1=C(SC2=C(C1=O)C=CC=C2)S | C[S:8](=O)[c:7]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:16](=[O:17])[c:15]2[c:10]([s:9]1)[cH:11][cH:12][cH:13][cH:14]2>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([SH:8])[s:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[c:16]1=[O:17] | CCOC(=O)c1c(S(C)=O)sc2ccccc2c1=O | CCOC(=O)c1c(S)sc2ccccc2c1=O | null | null | O1CCCC1 | Miscellaneous | OtherReaction | eef2e1b5ff0f69ab6081f09517432c05434b0ab0589dc0e3684a9e4e2f78d988 | b886beeb8fbfa84bb0f92183b9fe913660dce69c18077df92371b7c354b5aef5 | O=c1ccsc2ccccc12 | C-[S;H0;D3;+0:1](=O)-[c:2](:[#16;a:3]:[c:4]):[c:5]-[C:6](-[#8:7])=[O;D1;H0:8]>>[#8:7]-[C:6](=[O;D1;H0:8])-[c:5]:[c:2](-[SH;D1;+0:1]):[#16;a:3]:[c:4] | 23 | [{"value": 23.0, "product": "C(C)OC(=O)C1=C(SC2=C(C1=O)C=CC=C2)S", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 100 mg (0.337 mmol) of the compound of Example 18 in 1.8 ml of tetrahydrofuran was added 1N sodium hydrogensulfide (0.697 mmol), and the mixture was stirred for 3 hours. Solvent was distilled off and 87 mg of sodium bicarbonate and 6.5 ml of water were added to the residue, which was washed with dichlo... | 10.6084/m9.figshare.5104873.v1 | null | Sulfoxide | Aromatic thiol | null | null | c1csc2ccccc2c1 | HO- | O1CCCC1 | null | 3 | CCOC(=O)c1c(S(C)=O)sc2ccccc2c1=O>O1CCCC1>CCOC(=O)c1c(S)sc2ccccc2c1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c84f1c46a858498aa1a36a9d1af38093 | CI.COc1cc(C=O)c(Br)c(Cl)c1O>>COc1cc(C=O)c(Br)c(Cl)c1OC | BrC1=C(C(=C(C=C1C=O)OC)O)Cl.C1CCC2=NCCCN2CC1.CI.C(C)(C)N(CC)C(C)C.CI>>BrC1=C(C=O)C=C(C(=C1Cl)OC)OC | I[CH3:14].[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[c:8]([Br:9])[c:10]([Cl:11])[c:12]1[OH:13]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[c:8]([Br:9])[c:10]([Cl:11])[c:12]1[O:13][CH3:14] | CI.COc1cc(C=O)c(Br)c(Cl)c1O | COc1cc(C=O)c(Br)c(Cl)c1OC | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | b8b041187bac58376aae824630608e7deb49a01db3d652291f8b379c10d4e434 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | c1ccccc1 | I-[CH3;D1;+0:1].[OH;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:2]-[c:3](:[c:4]):[c:5] | 71 | [{"value": 71.0, "product": "BrC1=C(C=O)C=C(C(=C1Cl)OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | Into 50 ml of acetonitrile were suspended 5.39 g (20.3 mmol), of 6-bromo-5-chlorovanillin, and 3.04 ml (20.3 mmol) of 1.8-diazabicyclo[5,4,0]-7-undecene and 2.53 ml (40.6 mmol) of methyl iodide were added dropwise under cooling with ice. After stirred for 5 hours at room temperature, 3.9 ml (22.33 mmol) if diisopropyle... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | null | null | c1ccccc1 | HI | C(C)#N | null | 5 | CI.COc1cc(C=O)c(Br)c(Cl)c1O>C(C)#N>COc1cc(C=O)c(Br)c(Cl)c1OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-93c2e2181a674049914d3893aea5bed6 | CCOC(=O)CC(=O)c1cc(F)c(F)c(F)c1F.CI.S=C=S>>CCOC(=O)c1c(SC)sc2c(F)c(F)c(F)cc2c1=O | CI.FC1=C(C(=O)CC(=O)OCC)C=C(C(=C1F)F)F.C(=S)=S.C(C)N(CC)CC>>C(C)OC(=O)C1=C(SC2=C(C1=O)C=C(C(=C2F)F)F)SC | F[c:11]1[c:12]([F:13])[c:14]([F:15])[c:16]([F:17])[cH:18][c:19]1[C:20]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])=[O:21].I[CH3:9].[C:7](=[S:8])=[S:10]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([S:8][CH3:9])[s:10][c:11]2[c:12]([F:13])[c:14]([F:15])[c:16]([F:17])[cH:18][c:19]2[c:20]1=[O:21] | CCOC(=O)CC(=O)c1cc(F)c(F)c(F)c1F.CI.S=C=S | CCOC(=O)c1c(SC)sc2c(F)c(F)c(F)cc2c1=O | null | null | CS(=O)C | Aromatic Heterocycle Formation | OtherReaction | 90930908a1d7a3ae484483ce3381026d7c953f2f3989c0c515d480494eb0dab3 | fb7d04511983b89b4e1f5337b203cdb0ea7e85f9161a593cc23135d30f010fdc | O=c1ccsc2ccccc12 | F-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[C;H0;D3;+0:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12]):[c:13].I-[CH3;D1;+0:14].[S;H0;D1;+0:15]=[C;H0;D2;+0:16]=[S;H0;D1;+0:17]>>[C:12]-[#8:11]-[C:9](=[O;D1;H0:10])-[c;H0;D3;+0:8]1:[c;H0;D3;+0:6](=[O;D1;H0:7]):[c:5](:[c:13]):[c;H0;D3;+0:1](:[s;... | 74 | [{"value": 74.0, "product": "C(C)OC(=O)C1=C(SC2=C(C1=O)C=C(C(=C2F)F)F)SC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.8, "product": "C(C)OC(=O)C1=C(SC2=C(C1=O)C=C(C(=C2F)F)F)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 3.00 g (11.4 mmol) of ethyl 2,3,4,5-tetrafluorobenzoylacetate, 870 mg (11.4 mmol) of carbon disulfide and 9 ml of dried dimethyl sulfoxide were added 2.31 g (22.8 mmol) of triethylamine at room temperature, and the mixture was stirred for 1 hour at room temperature. Then, at room temperature, 3.24 g (2... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Ester | Ester.Monosulfide | c1ccccc1 | c1csc2ccccc2c1 | c1csc2ccccc2c1 | HF.I- | CS(=O)C | null | 1 | CCOC(=O)CC(=O)c1cc(F)c(F)c(F)c1F.CI.S=C=S>CS(=O)C>CCOC(=O)c1c(SC)sc2c(F)c(F)c(F)cc2c1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1649d4530bee447eb356e4adaeb56455 | CCOC(=O)c1c(SC)sc2c(F)c(F)c(F)cc2c1=O>>CSc1sc2c(F)c(F)c(F)cc2c(=O)c1C(=O)O | C(C)OC(=O)C1=C(SC2=C(C1=O)C=C(C(=C2F)F)F)SC.C(C)(=O)O.S(O)(O)(=O)=O>>C(=O)(O)C1=C(SC2=C(C1=O)C=C(C(=C2F)F)F)SC | CC[O:19][C:17]([c:16]1[c:3]([S:2][CH3:1])[s:4][c:5]2[c:6]([F:7])[c:8]([F:9])[c:10]([F:11])[cH:12][c:13]2[c:14]1=[O:15])=[O:18]>>[CH3:1][S:2][c:3]1[s:4][c:5]2[c:6]([F:7])[c:8]([F:9])[c:10]([F:11])[cH:12][c:13]2[c:14](=[O:15])[c:16]1[C:17](=[O:18])[OH:19] | CCOC(=O)c1c(SC)sc2c(F)c(F)c(F)cc2c1=O | CSc1sc2c(F)c(F)c(F)cc2c(=O)c1C(=O)O | null | null | O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1ccsc2ccccc12 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#16;a:6]>>[#16;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 54 | [{"value": 54.0, "product": "C(=O)(O)C1=C(SC2=C(C1=O)C=C(C(=C2F)F)F)SC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.6, "product": "C(=O)(O)C1=C(SC2=C(C1=O)C=C(C(=C2F)F)F)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 3 | HOUR | A mixture of 300 mg (0.897 mmol) of the compound of Example 111, 0.54 ml of acetic acid, 0.072 ml of concentrated sulfuric acid and 0.36 ml of water was stirred for 3 hours at 100° C. After cooling by allowing to stand, the crystals deposited were collected by filtration, washed with water, and dried to obtain 147 mg (... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1csc2ccccc2c1 | Other | O | 100 | 3 | CCOC(=O)c1c(SC)sc2c(F)c(F)c(F)cc2c1=O>O>CSc1sc2c(F)c(F)c(F)cc2c(=O)c1C(=O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-650824152b5742c386e87f846affa28e | COc1ccc(CCl)cc1.CSc1sc2c(F)c(F)c(F)cc2c(=O)c1C(=O)O>>COc1ccc(COC(=O)c2c(SC)sc3c(F)c(F)c(F)cc3c2=O)cc1 | C(=O)(O)C1=C(SC2=C(C1=O)C=C(C(=C2F)F)F)SC.COC1=CC=C(CCl)C=C1.C(C)N(CC)CC.[I-].[Na+]>>COC1=CC=C(COC(=O)C2=C(SC3=C(C2=O)C=C(C(=C3F)F)F)SC)C=C1 | Cl[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:28][cH:27]1.[OH:8][C:9](=[O:10])[c:11]1[c:12]([S:13][CH3:14])[s:15][c:16]2[c:17]([F:18])[c:19]([F:20])[c:21]([F:22])[cH:23][c:24]2[c:25]1=[O:26]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][C:9](=[O:10])[c:11]2[c:12]([S:13][CH3:14])[s:15][c:16]3[c:17]([F:18])[c:19]... | COc1ccc(CCl)cc1.CSc1sc2c(F)c(F)c(F)cc2c(=O)c1C(=O)O | COc1ccc(COC(=O)c2c(SC)sc3c(F)c(F)c(F)cc3c2=O)cc1 | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | O=C(OCc1ccccc1)c1csc2ccccc2c1=O | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#16;a:5]:[c:6]:[c:7]-[C:8](=[O;D1;H0:9])-[OH;D1;+0:10]>>[#16;a:5]:[c:6]:[c:7]-[C:8](=[O;D1;H0:9])-[O;H0;D2;+0:10]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 32.4 | [{"value": 32.0, "product": "COC1=CC=C(COC(=O)C2=C(SC3=C(C2=O)C=C(C(=C3F)F)F)SC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.4, "product": "COC1=CC=C(COC(=O)C2=C(SC3=C(C2=O)C=C(C(=C3F)F)F)SC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | To a suspension of 50 mg (0.163 mmol) of the compound of Example 112 in 0.2 ml of chloroform were added 30.7 mg (0.196 mmol) of p-methoxybenzyl chloride, 16.5 mg (0.163 mmol) of triethylamine and 29.4 mg (0.196 mmol) of sodium iodide, and the mixture was stirred for 5 hours at room temperature, which was poured into ic... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | c1ccccc1.c1csc2ccccc2c1 | HCl | C(Cl)(Cl)Cl | null | 5 | COc1ccc(CCl)cc1.CSc1sc2c(F)c(F)c(F)cc2c(=O)c1C(=O)O>C(Cl)(Cl)Cl>COc1ccc(COC(=O)c2c(SC)sc3c(F)c(F)c(F)cc3c2=O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-65534682ee6b4b1b840f36d71ebb8513 | Nc1cc([N+](=O)[O-])ccc1C=O>>Nc1ccc(C=O)c(N)c1 | NC1=C(C=O)C=CC(=C1)[N+](=O)[O-]>>NC1=C(C=O)C=CC(=C1)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([CH:6]=[O:7])[c:8]([NH2:9])[cH:10]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([CH:6]=[O:7])[c:8]([NH2:9])[cH:10]1 | Nc1cc([N+](=O)[O-])ccc1C=O | Nc1ccc(C=O)c(N)c1 | null | [Pd] | null | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | In a manner similar to that described for 10-nitro-20(RS)- and 10-nitro-20(S)-camptothecin, a mixture of 2-amino-4-nitrobenzaldehyde is treated with the tricyclic ketone 11 yielding 11-nitro-20(RS)- or 11-nitro-20(S)-camptothecin which in turn is reduced to 11-amino compound camptothecin by palladium/carbon. Alternativ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd] | null | null | Nc1cc([N+](=O)[O-])ccc1C=O>[Pd]>Nc1ccc(C=O)c(N)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-06f5c13d44cb4445b1c0ad64e71f27b9 | CCOC(=O)C1CCCN(C(=O)OC(C)(C)C)C1.ClCCCBr>>CCOC(=O)C12CCCN(CCC1)C2 | C(C)OC(=O)C1CN(CCC1)C(=O)OC(C)(C)C.C(C)(C)[N-]C(C)C.[Li+].O1CCCC1.BrCCCCl>>C(C)OC(=O)C12CCCN(CCC1)C2 | CC(C)(C)OC(=O)[N:10]1[CH2:9][CH2:8][CH2:7][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:14]1.Cl[CH2:13][CH2:12][CH2:11]Br>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]12[CH2:7][CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13]1)[CH2:14]2 | CCOC(=O)C1CCCN(C(=O)OC(C)(C)C)C1.ClCCCBr | CCOC(=O)C12CCCN(CCC1)C2 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | f0e6b5f83e3ba6a6fa98f66780a4137e5da2f647c6fa968f1e5e4d5e42ebd8b8 | 3f5dc1d93193b3e0a3d863cd886d5171d5b06000b75ac28593dfbd0f57ac702a | C1CC2CCCN(C1)C2 | Br-[CH2;D2;+0:1]-[C:2]-[CH2;D2;+0:3]-Cl.C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:4]1-[C:5]-[CH;D3;+0:6](-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10])-[C:11]-[C:12]-[C:13]-1>>[C:10]-[#8:9]-[C:7](=[O;D1;H0:8])-[C;H0;D4;+0:6]12-[C:5]-[N;H0;D3;+0:4](-[C:13]-[C:12]-[C:11]-1)-[CH2;D2;+0:1]-[C:2]-[CH2;D2;+0:3]-2 | 73 | [{"value": 73.0, "product": "C(C)OC(=O)C12CCCN(CCC1)C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.0, "product": "C(C)OC(=O)C12CCCN(CCC1)C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -35 | CELSIUS | 1 | HOUR | A cooled (-50° C.) solution of 1,3-piperidinedicarboxylic acid 1-(1,1-dimethylethyl) 3-ethyl ester (12.9 g, 50 mmol) in anhydrous tetrahydrofuran (60 mL) was treated (via syringe) with 1.15N lithium diisopropylamide/tetrahydorfuran (52 mmol), stirred for one hour at -15°±5° C., cooled (-35° C.), treated with 1-bromo-3-... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carbamic ester.Ester.Ether.Boc | Ester.Tertiary amine | C1CC[NH]CC1 | C1CC2CCCN(C1)C2 | C1CC2CCCN(C1)C2 | HCl.Br- | O1CCCC1 | -35 | 1 | CCOC(=O)C1CCCN(C(=O)OC(C)(C)C)C1.ClCCCBr>O1CCCC1>CCOC(=O)C12CCCN(CCC1)C2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3f6f7292f4214dacbbc44e42e9963d38 | CCOC(=O)C12CCCN(CC1)C2>>OCC12CCCN(CC1)C2 | [H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.O.[OH-].[Na+].O.C(C)OC(=O)C12CCCN(CC1)C2>>N12CCCC(CC1)(C2)CO | CCO[C:2](=[O:1])[C:3]12[CH2:4][CH2:5][CH2:6][N:7]([CH2:8][CH2:9]1)[CH2:10]2>>[OH:1][CH2:2][C:3]12[CH2:4][CH2:5][CH2:6][N:7]([CH2:8][CH2:9]1)[CH2:10]2 | CCOC(=O)C12CCCN(CC1)C2 | OCC12CCCN(CC1)C2 | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C1CC2CCN(C1)C2 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C:4])(-[C:5])-[C:6]-[#7:7]>>[#7:7]-[C:6]-[C:3](-[CH2;D2;+0:1]-[OH;D1;+0:2])(-[C:4])-[C:5] | null | [] | null | null | 30 | MINUTE | A cooled (0° C.) solution of 1.0N lithium aluminum hydride/tetrahydrofuran (55 mL, 55 mmol) under nitrogen was treated dropwise with a solution of 1-azabicyclo[3.2.1]octane-5-carboxylic acid ethyl ester (9.17 g, 50 mmol) in anhydrous tetrahydrofuran (20 mL), stirred for 30 minutes at room temperature, refluxed for one ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CC2CCN(C1)C2 | HO- | O1CCCC1 | null | 0.5 | CCOC(=O)C12CCCN(CC1)C2>O1CCCC1>OCC12CCCN(CC1)C2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-724adf2a51f8489d97c3c818d08a607f | CCOC(=O)C12CCCN(CCC1)C2>>OCC12CCCN(CCC1)C2 | O.[OH-].[Na+].O.C(C)OC(=O)C12CCCN(CCC1)C2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1>>N12CCCC(CCC1)(C2)CO | CCO[C:2](=[O:1])[C:3]12[CH2:4][CH2:5][CH2:6][N:7]([CH2:8][CH2:9][CH2:10]1)[CH2:11]2>>[OH:1][CH2:2][C:3]12[CH2:4][CH2:5][CH2:6][N:7]([CH2:8][CH2:9][CH2:10]1)[CH2:11]2 | CCOC(=O)C12CCCN(CCC1)C2 | OCC12CCCN(CCC1)C2 | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C1CC2CCCN(C1)C2 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C:4])(-[C:5])-[C:6]-[#7:7]>>[#7:7]-[C:6]-[C:3](-[CH2;D2;+0:1]-[OH;D1;+0:2])(-[C:4])-[C:5] | 98 | [{"value": 98.0, "product": "N12CCCC(CCC1)(C2)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.9, "product": "N12CCCC(CCC1)(C2)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A solution of 1-azabicyclo[3.3.1]nonane-5-carboxylic acid ethyl ester (9.08 g, 46 mmol) in anhydrous tetrahydrofuran (25 mL) was added dropwise to a cooled (-10° C.) solution of 1.0N lithium aluminum hydride/tetrahydrofuran (50 mL, 50 mmol) in a 3-neck, 250-mL flask under nitrogen at a rate to keep the reaction tempera... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CC2CCCN(C1)C2 | HO- | O1CCCC1 | null | 0.25 | CCOC(=O)C12CCCN(CCC1)C2>O1CCCC1>OCC12CCCN(CCC1)C2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a207e32502304f06a21da6f82ecce891 | NO.OCC12CCCN(CCC1)C2>>ON=CC12CCCN(CCC1)C2 | CS(=O)C.Cl.NO.C[O-].[Na+].CO.C[O-].[Na+].N12CCCC(CCC1)(C2)CO.C(C(=O)Cl)(=O)Cl>>N12CCCC(CCC1)(C2)C=NO | [OH:1][NH2:2].O[CH2:3][C:4]12[CH2:5][CH2:6][CH2:7][N:8]([CH2:9][CH2:10][CH2:11]1)[CH2:12]2>>[OH:1][N:2]=[CH:3][C:4]12[CH2:5][CH2:6][CH2:7][N:8]([CH2:9][CH2:10][CH2:11]1)[CH2:12]2 | NO.OCC12CCCN(CCC1)C2 | ON=CC12CCCN(CCC1)C2 | null | null | C(Cl)Cl.C(C)N(CC)CC | Heteroatom Alkylation and Arylation | OtherReaction | 6e036145121e74fec2a8b1c98baa36a6154968367991affa3e65663e26a5dd0f | 5b1c2692f91b6028790c632ddd5f7bb4ef9cf197bdd095bee03fa688aa8c3259 | C1CC2CCCN(C1)C2 | O-[CH2;D2;+0:1]-[C:2](-[C:3])(-[C:4])-[C:5]-[#7:6].[NH2;D1;+0:7]-[O;D1;H1:8]>>[#7:6]-[C:5]-[C:2](-[CH;D2;+0:1]=[N;H0;D2;+0:7]-[O;D1;H1:8])(-[C:3])-[C:4] | 60 | [{"value": 60.0, "product": "N12CCCC(CCC1)(C2)C=NO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.9, "product": "N12CCCC(CCC1)(C2)C=NO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A cooled (-65° C.) solution of oxalyl chloride (5.3 mL, 60 mmol) in anhydrous methylene chloride (100 mL) under nitrogen was treated dropwise with anhydrous dimethylsulfoxide (0.60 g, 120 mmol) in methylene chloride (30 mL) at a rate to keep the reaction temperature below -60° C. After 30 minutes at -65° C., a solution... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary amine | Oxime | null | null | C1CC2CCCN(C1)C2 | HO- | C(Cl)Cl.C(C)N(CC)CC | null | 0.5 | NO.OCC12CCCN(CCC1)C2>C(Cl)Cl.C(C)N(CC)CC>ON=CC12CCCN(CCC1)C2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-37ba75b1b1944de596d5785b37bb6bfe | COC(=O)C12CCCN(CCC1)C2.N>>NC(=O)C12CCCN(CCC1)C2 | COC(=O)C12CCCN(CCC1)C2.N>>N12CCCC(CCC1)(C2)C(=O)N | CO[C:2](=[O:3])[C:4]12[CH2:5][CH2:6][CH2:7][N:8]([CH2:9][CH2:10][CH2:11]1)[CH2:12]2.[NH3:1]>>[NH2:1][C:2](=[O:3])[C:4]12[CH2:5][CH2:6][CH2:7][N:8]([CH2:9][CH2:10][CH2:11]1)[CH2:12]2 | COC(=O)C12CCCN(CCC1)C2.N | NC(=O)C12CCCN(CCC1)C2 | null | C[O-].[Na+].CO | CO | Acylation | OtherReaction | d5b10d4f469e7a196a3b04a6a9e159a7d90514b6df5b50c1197d4b1b774c04e1 | adc0ef6f6c1340dd2dbab737c85bf17fc842769181c5db1a2b4f82b391b28f9f | C1CC2CCCN(C1)C2 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C:5])-[C:6]-[#7:7].[NH3;D0;+0:8]>>[#7:7]-[C:6]-[C:3](-[C;H0;D3;+0:1](-[NH2;D1;+0:8])=[O;D1;H0:2])(-[C:4])-[C:5] | 38 | [{"value": 38.0, "product": "N12CCCC(CCC1)(C2)C(=O)N", "details": "PERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | A solution of 1-azabicyclo[3.3.1]nonane-5-carboxylic acid methyl ester (1.83 g, 10 mmol) in ammonia (50 mL) and methanol (20 mL) was sealed in a bomb and heated at 120°-130° C. for 36 hours (gas chromatography indicated that the reaction was incomplete). Three drops of 25% sodium methoxide/methanol were added, and the ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary amide | null | null | C1CC2CCCN(C1)C2 | HO- | C[O-].[Na+].CO.CO | 150 | null | COC(=O)C12CCCN(CCC1)C2.N>C[O-].[Na+].CO.CO>NC(=O)C12CCCN(CCC1)C2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0445a3a91b3b46b584c36be6a9648625 | NC(=O)C12CCCN(CCC1)C2>>NCC12CCCN(CCC1)C2 | O.[OH-].[Na+].O.N12CCCC(CCC1)(C2)C(=O)N.[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1>>N12CCCC(CCC1)(C2)CN | O=[C:2]([NH2:1])[C:3]12[CH2:4][CH2:5][CH2:6][N:7]([CH2:8][CH2:9][CH2:10]1)[CH2:11]2>>[NH2:1][CH2:2][C:3]12[CH2:4][CH2:5][CH2:6][N:7]([CH2:8][CH2:9][CH2:10]1)[CH2:11]2 | NC(=O)C12CCCN(CCC1)C2 | NCC12CCCN(CCC1)C2 | null | null | CCOCC.O1CCCC1 | Reduction | Reduction of primary amides to amines | 71f4ab6e4ff9fd6ad8fb6a6879cdc6c258d35bb85b9b40ad2783b874bf909ba4 | 8776a0c3e2f32dafe87200a597cd55df0b01414bf133bdc9f8f7e1171014bfad | C1CC2CCCN(C1)C2 | O=[C;H0;D3;+0:1](-[N;D1;H2:2])-[C:3](-[C:4])(-[C:5])-[C:6]-[#7:7]>>[#7:7]-[C:6]-[C:3](-[CH2;D2;+0:1]-[N;D1;H2:2])(-[C:4])-[C:5] | 77 | [{"value": 77.0, "product": "N12CCCC(CCC1)(C2)CN", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.9, "product": "N12CCCC(CCC1)(C2)CN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | A suspension of 1-azabicyclo[3.3.1]nonane-5-carboxamide (1.80 g, 10.7 mmol) in anhydrous tetrahydrofuran (10 mL) under nitrogen was treated (via syringe) with 1.0N lithium aluminum hydride/tetrahydrofuran (25 mL, 25 mmol), and the mixture was refluxed for 4 hours and cooled (0° C.). The mixture was treated carefully dr... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide | null | null | null | C1CC2CCCN(C1)C2 | Other | CCOCC.O1CCCC1 | 0 | null | NC(=O)C12CCCN(CCC1)C2>CCOCC.O1CCCC1>NCC12CCCN(CCC1)C2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-042aee9b85f3448db5bd4bc2f82e203c | COS(=O)(=O)OC.O=C(O)c1c[nH]c2ccccc12>>Cn1cc(C(=O)O)c2ccccc21 | [H-].[Na+].N1C=C(C2=CC=CC=C12)C(=O)O.[OH-].[Na+].COS(=O)(=O)OC>>CN1C=C(C2=CC=CC=C12)C(=O)O | COS(=O)(=O)O[CH3:1].[nH:2]1[cH:3][c:4]([C:5](=[O:6])[OH:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12>>[CH3:1][n:2]1[cH:3][c:4]([C:5](=[O:6])[OH:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12 | COS(=O)(=O)OC.O=C(O)c1c[nH]c2ccccc12 | Cn1cc(C(=O)O)c2ccccc21 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-methylation | 5ce73e9bd608d5491381e563c654ad03f655de6d7aa46423d6263e854c49919a | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | c1ccc2[nH]ccc2c1 | C-O-S(=O)(=O)-O-[CH3;D1;+0:1].[O;D1;H0:2]=[C:3](-[O;D1;H1:4])-[c:5]1:[c:6]:[nH;D2;+0:7]:[c:8](:[c:9]):[c:10]:1>>[CH3;D1;+0:1]-[n;H0;D3;+0:7]1:[c:6]:[c:5](-[C:3](=[O;D1;H0:2])-[O;D1;H1:4]):[c:10]:[c:8]:1:[c:9] | 75.3 | [{"value": 75.0, "product": "CN1C=C(C2=CC=CC=C12)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.3, "product": "CN1C=C(C2=CC=CC=C12)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 30 | MINUTE | A cooled (0° C.) suspension of 60% sodium hydride-oil dispersion (0.96 g, 24 mmol) in anhydrous N,N-dimethylformamide (15 mL) under nitrogen was treated in portions with indole-3-carboxylic acid (1.62 g, 10 mmol), and the mixture was stirred at 45°±5° C. for 30 minutes. Dimethylsulfate (3.03 g, 24 mmol) was added, and ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2[nH]ccc2c1 | c1c[nH]c2ccccc12 | c1c[nH]c2ccccc12 | HO- | CN(C=O)C | 100 | 0.5 | COS(=O)(=O)OC.O=C(O)c1c[nH]c2ccccc12>CN(C=O)C>Cn1cc(C(=O)O)c2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-76e193244c0648009545e2db9839eabd | COC(=O)c1nn(C)c2ccccc12>>Cn1nc(C(=O)O)c2ccccc21 | Cl.CN1N=C(C2=CC=CC=C12)C(=O)OC.[OH-].[Na+]>>CN1N=C(C2=CC=CC=C12)C(=O)O | C[O:7][C:5]([c:4]1[n:3][n:2]([CH3:1])[c:13]2[c:8]1[cH:9][cH:10][cH:11][cH:12]2)=[O:6]>>[CH3:1][n:2]1[n:3][c:4]([C:5](=[O:6])[OH:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12 | COC(=O)c1nn(C)c2ccccc12 | Cn1nc(C(=O)O)c2ccccc21 | null | null | CO.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2[nH]ncc2c1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#7;a:5]:[#7;a:6]>>[#7;a:6]:[#7;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 92.1 | [{"value": 92.0, "product": "CN1N=C(C2=CC=CC=C12)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.1, "product": "CN1N=C(C2=CC=CC=C12)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1-methylindazole-3-carboxylic acid, methyl ester (1.00 g, 0.0053 mol) was stirred in a mixture of methanol (10 mL)/2N NaOH solution (120 mL) at reflux temperature for 2 hours. After cooling, the mixture was diluted with water (100 mL) and acidified with 6N HCl solution. The white solid that formed was col... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1n[nH]c2ccccc12 | Other | CO.O | null | null | COC(=O)c1nn(C)c2ccccc12>CO.O>Cn1nc(C(=O)O)c2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b8ad3a760b1242ffb810507057579d5e | COc1cc(N)c(Cl)cc1C(=O)O>>Nc1cc(O)c(C(=O)O)cc1Cl | [H-].[Na+].C(C)S.NC1=CC(=C(C(=O)O)C=C1Cl)OC>>NC1=CC(=C(C(=O)O)C=C1Cl)O | C[O:5][c:4]1[cH:3][c:2]([NH2:1])[c:11]([Cl:12])[cH:10][c:6]1[C:7](=[O:8])[OH:9]>>[NH2:1][c:2]1[cH:3][c:4]([OH:5])[c:6]([C:7](=[O:8])[OH:9])[cH:10][c:11]1[Cl:12] | COc1cc(N)c(Cl)cc1C(=O)O | Nc1cc(O)c(C(=O)O)cc1Cl | null | null | CN(C=O)C | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]>>[O;D1;H0:6]=[C:5](-[O;D1;H1:7])-[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 83.4 | [{"value": 83.0, "product": "NC1=CC(=C(C(=O)O)C=C1Cl)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.4, "product": "NC1=CC(=C(C(=O)O)C=C1Cl)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A cooled (5° C.) suspension of 60% sodium hydride/oil dispersion (20.0 g, 0.50 mole) in anhydrous dimethylformamide (300 mL) under nitrogen was treated slowly dropwise with ethyl mercaptan (18.7 g, 0.30 mole) so as to maintain a pot temperature below 15° C., then stirred at room temperature for 15 minutes, cooled (5° C... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1 | Other | CN(C=O)C | null | 0.25 | COc1cc(N)c(Cl)cc1C(=O)O>CN(C=O)C>Nc1cc(O)c(C(=O)O)cc1Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5ef4854df60141d78ca949d2c8047a2b | CO.Nc1cc(O)c(C(=O)O)cc1Cl>>COC(=O)c1cc(Cl)c(N)cc1O | S(=O)(=O)(OC)OC.NC1=CC(=C(C(=O)O)C=C1Cl)O.C[O-].[Na+].CO>>NC1=CC(=C(C(=O)OC)C=C1Cl)O | O[CH3:1].[OH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[c:9]([NH2:10])[cH:11][c:12]1[OH:13]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[c:9]([NH2:10])[cH:11][c:12]1[OH:13] | CO.Nc1cc(O)c(C(=O)O)cc1Cl | COC(=O)c1cc(Cl)c(N)cc1O | null | null | CO.O | Heteroatom Alkylation and Arylation | Esterification of Carboxylic Acids | 961bfcd5802efbb4a2d5a1e38cbfb6654b5b78f769c3570df49b858a6f105ab6 | 0a622556a49b258b9020bd3a5bdd1fa9237e7093cf9b09de3a6b575ffe935dcd | c1ccccc1 | O-[CH3;D1;+0:1].[O;D1;H0:2]=[C:3](-[OH;D1;+0:4])-[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:4]-[C:3](=[O;D1;H0:2])-[c:5] | 87 | [{"value": 87.0, "product": "NC1=CC(=C(C(=O)OC)C=C1Cl)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.8, "product": "NC1=CC(=C(C(=O)OC)C=C1Cl)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of 4-amino-5-chloro-2-hydroxybenzoic acid (1.88 g, 10 mmol) in absolute methanol (20 mL) was treated with 25% sodium methoxide/methanol (2.16 g, 10 mmol), stirred for 30 minutes, and concentrated in vacuo. The solid residue was taken up in anhydrous acetone (30 mL), treated with dimethyl sulfate (1.64 g, 13 ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | CO.O | null | 0.5 | CO.Nc1cc(O)c(C(=O)O)cc1Cl>CO.O>COC(=O)c1cc(Cl)c(N)cc1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4901bf8f54dc48a7ac09c0ddf6fdf741 | COC(=O)c1cc(Cl)c(N)cc1O.COCCBr>>COCCOc1cc(N)c(Cl)cc1C(=O)OC | O.COC(C1=C(C=C(C(=C1)Cl)N)O)=O.[H-].[Na+].COCCBr>>COC(C1=C(C=C(C(=C1)Cl)N)OCCOC)=O | [OH:5][c:6]1[cH:7][c:8]([NH2:9])[c:10]([Cl:11])[cH:12][c:13]1[C:14](=[O:15])[O:16][CH3:17].Br[CH2:4][CH2:3][O:2][CH3:1]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]([NH2:9])[c:10]([Cl:11])[cH:12][c:13]1[C:14](=[O:15])[O:16][CH3:17] | COC(=O)c1cc(Cl)c(N)cc1O.COCCBr | COCCOc1cc(N)c(Cl)cc1C(=O)OC | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2]-[#8:3]):[c:10] | 53 | [{"value": 53.0, "product": "COC(C1=C(C=C(C(=C1)Cl)N)OCCOC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.9, "product": "COC(C1=C(C=C(C(=C1)Cl)N)OCCOC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A suspension of 60% sodium hydride/oil dispersion (1.00 g, 25 mmol) in anhydrous dimethylformamide (40 mL) under nitrogen was treated with 4-amino-5-chloro-2-hydroxybenzoic acid methyl ester (4.03 g, 20 mmol), stirred for 30 minutes, then treated with 2-bromoethyl methyl ether (3.48 g, 25 mmol). The mixture was heated ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | CN(C=O)C | null | 0.5 | COC(=O)c1cc(Cl)c(N)cc1O.COCCBr>CN(C=O)C>COCCOc1cc(N)c(Cl)cc1C(=O)OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1be6548ad9b94f2f8afd6c1d75cd9889 | COCCOc1cc(N)c(Cl)cc1C(=O)OC>>COCCOc1cc(N)c(Cl)cc1C(=O)O | COC(C1=C(C=C(C(=C1)Cl)N)OCCOC)=O.[OH-].[Na+].O>>NC1=CC(=C(C(=O)O)C=C1Cl)OCCOC | C[O:16][C:14]([c:13]1[c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[cH:7][c:8]([NH2:9])[c:10]([Cl:11])[cH:12]1)=[O:15]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]([NH2:9])[c:10]([Cl:11])[cH:12][c:13]1[C:14](=[O:15])[OH:16] | COCCOc1cc(N)c(Cl)cc1C(=O)OC | COCCOc1cc(N)c(Cl)cc1C(=O)O | null | null | C(C)O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 78 | [{"value": 75.0, "product": "NC1=CC(=C(C(=O)O)C=C1Cl)OCCOC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.0, "product": "NC1=CC(=C(C(=O)O)C=C1Cl)OCCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-amino-5-chloro-2-(2-methoxyethoxy)benzoic acid methyl ester (2.75 g, 10.6 mmol) in 95% ethanol (20 mL) was treated with 50% sodium hydroxide (10 mL) and water (10 mL), and refluxed for one hour. The ethanol was removed in vacuo and replaced with water. The aqueous solution was extracted with ether (20 m... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | C(C)O | null | null | COCCOc1cc(N)c(Cl)cc1C(=O)OC>C(C)O>COCCOc1cc(N)c(Cl)cc1C(=O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-55c482b078c24bb4b5e2982805ae9829 | COC(=O)c1ccc(N)cc1.CS(=O)(=O)Cl>>COC(=O)c1ccc(NS(C)(=O)=O)cc1 | Cl.CS(=O)(=O)Cl.N1=CC=CC=C1.NC1=CC=C(C(=O)OC)C=C1>>COC(C1=CC=C(C=C1)NS(=O)(=O)C)=O | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:14][cH:15]1.Cl[S:10]([CH3:11])(=[O:12])=[O:13]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][S:10]([CH3:11])(=[O:12])=[O:13])[cH:14][cH:15]1 | COC(=O)c1ccc(N)cc1.CS(=O)(=O)Cl | COC(=O)c1ccc(NS(C)(=O)=O)cc1 | null | null | C(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | c1ccccc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 95.2 | [{"value": 91.5, "product": "COC(C1=CC=C(C=C1)NS(=O)(=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.2, "product": "COC(C1=CC=C(C=C1)NS(=O)(=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of methanesulfonyl chloride (15.2 g, 132 mmol) in methylene chloride (50 mL) was added dropwise to a stirring slurry of pyridine (41.8 g, 529 mmol) and methyl 4-aminobenzoate (20.0 g, 132 mmol) in methylene chloride (110 mL) cooled by a dry ice/acetone bath. The reaction mixture was allowed to warm to ambien... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1 | HCl | C(Cl)Cl | null | 8 | COC(=O)c1ccc(N)cc1.CS(=O)(=O)Cl>C(Cl)Cl>COC(=O)c1ccc(NS(C)(=O)=O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d21c947da703415f83c8dca17871db03 | CCN(CC)C(=O)COc1cc(N)c(Cl)cc1C(=O)OC>>CCN(CC)C(=O)COc1cc(N)c(Cl)cc1C(=O)O | Cl.[OH-].[Na+].NC1=CC(=C(C(=O)OC)C=C1Cl)OCC(=O)N(CC)CC.CO>>NC1=CC(=C(C(=O)O)C=C1Cl)OCC(=O)N(CC)CC | C[O:20][C:18]([c:17]1[c:10]([O:9][CH2:8][C:6]([N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])=[O:7])[cH:11][c:12]([NH2:13])[c:14]([Cl:15])[cH:16]1)=[O:19]>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[C:6](=[O:7])[CH2:8][O:9][c:10]1[cH:11][c:12]([NH2:13])[c:14]([Cl:15])[cH:16][c:17]1[C:18](=[O:19])[OH:20] | CCN(CC)C(=O)COc1cc(N)c(Cl)cc1C(=O)OC | CCN(CC)C(=O)COc1cc(N)c(Cl)cc1C(=O)O | null | null | O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 68.1 | [{"value": 68.0, "product": "NC1=CC(=C(C(=O)O)C=C1Cl)OCC(=O)N(CC)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.1, "product": "NC1=CC(=C(C(=O)O)C=C1Cl)OCC(=O)N(CC)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A solution of 4-amino-5-chloro-2-[2-(diethylamino)-2-oxoethoxy]benzoic acid, methyl ester (7.87 g, 25 mmol) in water (70 g) containing methanol (40 g) was treated with 50% sodium hydroxide (10 g) and heated to 60° C. for 30 minutes. The mixture was neutralized with 3N HCl until a precipitate formed (pH 3), and the soli... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | O | 60 | null | CCN(CC)C(=O)COc1cc(N)c(Cl)cc1C(=O)OC>O>CCN(CC)C(=O)COc1cc(N)c(Cl)cc1C(=O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-257d8a8cf6e94ad4a79fa20e809fe6eb | C=CCBr.COC(=O)c1cc(Cl)c(N)cc1O>>C=CCOc1cc(N)c(Cl)cc1C(=O)O | O.COC(C1=C(C=C(C(=C1)Cl)N)O)=O.[H-].[Na+].C(C=C)Br>>NC1=CC(=C(C(=O)O)C=C1Cl)OCC=C | Br[CH2:3][CH:2]=[CH2:1].C[O:15][C:13]([c:12]1[c:5]([OH:4])[cH:6][c:7]([NH2:8])[c:9]([Cl:10])[cH:11]1)=[O:14]>>[CH2:1]=[CH:2][CH2:3][O:4][c:5]1[cH:6][c:7]([NH2:8])[c:9]([Cl:10])[cH:11][c:12]1[C:13](=[O:14])[OH:15] | C=CCBr.COC(=O)c1cc(Cl)c(N)cc1O | C=CCOc1cc(N)c(Cl)cc1C(=O)O | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | c47049bacd28cc701f2e77df376a2fcefecd5392e081f9a62473cff265d23a8c | 017337a0828c32d10d28543003ae15a8b492b5e2f69019c65a4461eabc617d95 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].C-[O;H0;D2;+0:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[C;D1;H2:3]=[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-[c:8](:[c:10]):[c:7]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:4] | 62.2 | [{"value": 62.2, "product": "NC1=CC(=C(C(=O)O)C=C1Cl)OCC=C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.2, "product": "NC1=CC(=C(C(=O)O)C=C1Cl)OCC=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A suspension of 60% sodium hydride/oil dispersion (1.52 g, 38 mmol) in anhydrous dimethylformamide (50 mL) under nitrogen was treated in portions with 4-amino-5-chloro-2-hydroxybenzoic acid methyl ester (6.05 g, 30 mmol), stirred at room temperature for 30 minutes, and treated with allyl bromide (4.60 g, 38 mmol). The ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Carboxylic acid.Ether | null | null | c1ccccc1 | HBr | CN(C=O)C | null | 0.5 | C=CCBr.COC(=O)c1cc(Cl)c(N)cc1O>CN(C=O)C>C=CCOc1cc(N)c(Cl)cc1C(=O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4a61892e548641678c1f2f77ac5daff8 | CSCCCl.Nc1cc(O)c(C(=O)O)cc1Cl>>CSCCOc1cc(N)c(Cl)cc1C(=O)O | [H-].[Na+].NC1=CC(=C(C(=O)O)C=C1Cl)O.ClCCSC>>NC1=CC(=C(C(=O)O)C=C1Cl)OCCSC | Cl[CH2:4][CH2:3][S:2][CH3:1].[OH:5][c:6]1[cH:7][c:8]([NH2:9])[c:10]([Cl:11])[cH:12][c:13]1[C:14](=[O:15])[OH:16]>>[CH3:1][S:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]([NH2:9])[c:10]([Cl:11])[cH:12][c:13]1[C:14](=[O:15])[OH:16] | CSCCCl.Nc1cc(O)c(C(=O)O)cc1Cl | CSCCOc1cc(N)c(Cl)cc1C(=O)O | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#16:3].[O;D1;H0:4]=[C:5](-[O;D1;H1:6])-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[#16:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-[c:8](:[c:10]):[c:7]-[C:5](=[O;D1;H0:4])-[O;D1;H1:6] | 57 | [{"value": 57.0, "product": "NC1=CC(=C(C(=O)O)C=C1Cl)OCCSC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.5, "product": "NC1=CC(=C(C(=O)O)C=C1Cl)OCCSC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 15 | MINUTE | A cooled (5° C.) suspension of 60% sodium hydride oil dispersion (0.52 g, 13 mmoles) in anhydrous dimethylformamide (15 mL) under nitrogen was treated in portions with 4-amino-5-chloro-2-hydroxybenzoic acid (0.94 g, 5 mmoles), stirred for 15 minutes at 25° C., treated with (2-chloroethyl)methyl sulfide (1.66 g, 15 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HCl | CN(C=O)C | 25 | 0.25 | CSCCCl.Nc1cc(O)c(C(=O)O)cc1Cl>CN(C=O)C>CSCCOc1cc(N)c(Cl)cc1C(=O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-40169b770c9f42239cde7e0d4cb368b9 | COc1cc(N)c(Cl)cc1C(=O)O.NCC12CCCN(CC1)C2>>COc1cc(N)c(Cl)cc1C(=O)NCC12CCCN(CC1)C2 | NC1=CC(=C(C(=O)O)C=C1Cl)OC.C(=O)(N1C=NC=C1)N1C=NC=C1.N12CCCC(CC1)(C2)CN>>NC1=CC(=C(C(=O)NCC23CCCN(CC2)C3)C=C1Cl)OC | O[C:11]([c:10]1[c:3]([O:2][CH3:1])[cH:4][c:5]([NH2:6])[c:7]([Cl:8])[cH:9]1)=[O:12].[NH2:13][CH2:14][C:15]12[CH2:16][CH2:17][CH2:18][N:19]([CH2:20][CH2:21]1)[CH2:22]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[c:7]([Cl:8])[cH:9][c:10]1[C:11](=[O:12])[NH:13][CH2:14][C:15]12[CH2:16][CH2:17][CH2:18][N:19]([CH2:20][CH2:21]1)[C... | COc1cc(N)c(Cl)cc1C(=O)O.NCC12CCCN(CC1)C2 | COc1cc(N)c(Cl)cc1C(=O)NCC12CCCN(CC1)C2 | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCC12CCCN(CC1)C2)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 70 | [{"value": 70.0, "product": "NC1=CC(=C(C(=O)NCC23CCCN(CC2)C3)C=C1Cl)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.8, "product": "NC1=CC(=C(C(=O)NCC23CCCN(CC2)C3)C=C1Cl)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A suspension of 4-amino-5-chloro-2-methoxybenzoic acid (1.72 g, 8.5 mmol) in anhydrous tetrahydrofuan (10 mL) under nitrogen was treated with 1,1'-carbonyldiimidazole (1.46 g, 9.0 mmol), stirred for one hour, then degassed under a stream of nitrogen for 10 minutes. A solution of 1-azabicyclo[3.2.1]octane-5-methanamine ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC2CCN(C1)C2 | HO- | O1CCCC1 | null | 1 | COc1cc(N)c(Cl)cc1C(=O)O.NCC12CCCN(CC1)C2>O1CCCC1>COc1cc(N)c(Cl)cc1C(=O)NCC12CCCN(CC1)C2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2a7ae11fb7f447428407b154948c0592 | CNc1cc(OC)c(C(=O)O)cc1Cl.NCC12CCCN(CCC1)C2>>CNc1cc(OC)c(C(=O)NCC23CCCN(CCC2)C3)cc1Cl | N12CCCC(CCC1)(C2)CN.ClC=1C(=CC(=C(C(=O)O)C1)OC)NC.C(=O)(N1C=NC=C1)N1C=NC=C1>>N12CCCC(CCC1)(C2)CNC(C2=C(C=C(C(=C2)Cl)NC)OC)=O | O[C:9]([c:8]1[c:5]([O:6][CH3:7])[cH:4][c:3]([NH:2][CH3:1])[c:23]([Cl:24])[cH:22]1)=[O:10].[NH2:11][CH2:12][C:13]12[CH2:14][CH2:15][CH2:16][N:17]([CH2:18][CH2:19][CH2:20]1)[CH2:21]2>>[CH3:1][NH:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8]([C:9](=[O:10])[NH:11][CH2:12][C:13]23[CH2:14][CH2:15][CH2:16][N:17]([CH2:18][CH2:19][CH2... | CNc1cc(OC)c(C(=O)O)cc1Cl.NCC12CCCN(CCC1)C2 | CNc1cc(OC)c(C(=O)NCC23CCCN(CCC2)C3)cc1Cl | null | null | CO.O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCC12CCCN(CCC1)C2)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 73.3 | [{"value": 73.0, "product": "N12CCCC(CCC1)(C2)CNC(C2=C(C=C(C(=C2)Cl)NC)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.3, "product": "N12CCCC(CCC1)(C2)CNC(C2=C(C=C(C(=C2)Cl)NC)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | A solution of 5-chloro-2-methoxy-4-(methylamino)benzoic acid (1.08 g, 5 mmol) in anhydrous tetrahydrofuran (7 mL) under nitrogen was treated with 1,1'-carbonyldiimidazole (0.90 g, 5.5 mmol), stirred one hour, degassed under a stream of nitrogen for 10 minutes, and cooled (0° C.). A solution of 1-azabicyclo[3.3.1]nonane... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC2CCCN(C1)C2 | HO- | CO.O1CCCC1 | 0 | 1 | CNc1cc(OC)c(C(=O)O)cc1Cl.NCC12CCCN(CCC1)C2>CO.O1CCCC1>CNc1cc(OC)c(C(=O)NCC23CCCN(CCC2)C3)cc1Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-27b03df9a5db4ae9b9cafbfe76f1aac5 | COCCOc1cc(N)c(Cl)cc1C(=O)O.NCC12CCCN(CCC1)C2>>COCCOc1cc(N)c(Cl)cc1C(=O)NCC12CCCN(CCC1)C2 | N12CCCC(CCC1)(C2)CN.NC1=CC(=C(C(=O)O)C=C1Cl)OCCOC.C(=O)(N1C=NC=C1)N1C=NC=C1>>NC1=CC(=C(C(=O)NCC23CCCN(CCC2)C3)C=C1Cl)OCCOC | O[C:14]([c:13]1[c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[cH:7][c:8]([NH2:9])[c:10]([Cl:11])[cH:12]1)=[O:15].[NH2:16][CH2:17][C:18]12[CH2:19][CH2:20][CH2:21][N:22]([CH2:23][CH2:24][CH2:25]1)[CH2:26]2>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]([NH2:9])[c:10]([Cl:11])[cH:12][c:13]1[C:14](=[O:15])[NH:16][CH2:17][C:18]1... | COCCOc1cc(N)c(Cl)cc1C(=O)O.NCC12CCCN(CCC1)C2 | COCCOc1cc(N)c(Cl)cc1C(=O)NCC12CCCN(CCC1)C2 | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCC12CCCN(CCC1)C2)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 49 | [{"value": 49.0, "product": "NC1=CC(=C(C(=O)NCC23CCCN(CCC2)C3)C=C1Cl)OCCOC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.0, "product": "NC1=CC(=C(C(=O)NCC23CCCN(CCC2)C3)C=C1Cl)OCCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | A solution of 4-amino-5-chloro-2-(2-methoxyethoxy)benzoic acid (2.09 g, 8.5 mmol) in anhydrous tetrahydrofuran (10 mL) under nitrogen was treated with 1,1'-carbonyldiimidazole (1.46 g, 9.0 mmol), stirred for one hour, degassed under a stream of nitrogen over 10 minutes, and cooled (0° C.). A solution of 1-azabicyclo[3.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC2CCCN(C1)C2 | HO- | O1CCCC1 | 0 | 1 | COCCOc1cc(N)c(Cl)cc1C(=O)O.NCC12CCCN(CCC1)C2>O1CCCC1>COCCOc1cc(N)c(Cl)cc1C(=O)NCC12CCCN(CCC1)C2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-29b0a5406f954cd686619309354da83b | NCC12CCCN(CCC1)C2.O=C(O)c1c[nH]c2ccccc12>>O=C(NCC12CCCN(CCC1)C2)c1c[nH]c2ccccc12 | C[O-].[Na+].CO.S(=O)(Cl)Cl.N12CCCC(CCC1)(C2)CN.C(C)N(CC)CC.N1C=C(C2=CC=CC=C12)C(=O)O>>N12CCCC(CCC1)(C2)CNC(=O)C2=CNC1=CC=CC=C21 | [NH2:3][CH2:4][C:5]12[CH2:6][CH2:7][CH2:8][N:9]([CH2:10][CH2:11][CH2:12]1)[CH2:13]2.O[C:2](=[O:1])[c:14]1[cH:15][nH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12>>[O:1]=[C:2]([NH:3][CH2:4][C:5]12[CH2:6][CH2:7][CH2:8][N:9]([CH2:10][CH2:11][CH2:12]1)[CH2:13]2)[c:14]1[cH:15][nH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22... | NCC12CCCN(CCC1)C2.O=C(O)c1c[nH]c2ccccc12 | O=C(NCC12CCCN(CCC1)C2)c1c[nH]c2ccccc12 | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCC12CCCN(CCC1)C2)c1c[nH]c2ccccc12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[c:7]:1.[C:8]-[C:9]-[NH2;D1;+0:10]>>[C:8]-[C:9]-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[c:7]:1 | 57.2 | [{"value": 57.0, "product": "N12CCCC(CCC1)(C2)CNC(=O)C2=CNC1=CC=CC=C21", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.2, "product": "N12CCCC(CCC1)(C2)CNC(=O)C2=CNC1=CC=CC=C21", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 55 | CELSIUS | 1 | HOUR | A cooled (0° C.) suspension/solution of indole-3-carboxylic acid (0.92 g, 5.7 mmol) in anhydrous tetrahydrofuran (10 mL) was treated dropwise with thionyl chloride (0.72 g, 6.0 mmol), and the solution was refluxed for one hour and concentrated in vacuo. A cooled (0° C.) solution of 1-azabicyclo[3.3.1]nonane-5-methanami... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CC2CCCN(C1)C2.c1ccc2[nH]ccc2c1 | HO- | O1CCCC1 | 55 | 1 | NCC12CCCN(CCC1)C2.O=C(O)c1c[nH]c2ccccc12>O1CCCC1>O=C(NCC12CCCN(CCC1)C2)c1c[nH]c2ccccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5e3856e4880a45e59753efe824ac617e | Cn1cc(C(=O)O)c2ccccc21.NCC12CCCN(CCC1)C2>>O=C(NCC12CCCN(CCC1)C2)c1c[nH]c2ccccc12 | N12CCCC(CCC1)(C2)CN.CN1C=C(C2=CC=CC=C12)C(=O)O.C(=O)(N1C=NC=C1)N1C=NC=C1.CN(C=O)C>>N12CCCC(CCC1)(C2)CNC(=O)C2=CNC1=CC=CC=C21 | C[n:16]1[cH:15][c:14]([C:2](O)=[O:1])[c:22]2[c:17]1[cH:18][cH:19][cH:20][cH:21]2.[NH2:3][CH2:4][C:5]12[CH2:6][CH2:7][CH2:8][N:9]([CH2:10][CH2:11][CH2:12]1)[CH2:13]2>>[O:1]=[C:2]([NH:3][CH2:4][C:5]12[CH2:6][CH2:7][CH2:8][N:9]([CH2:10][CH2:11][CH2:12]1)[CH2:13]2)[c:14]1[cH:15][nH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:... | Cn1cc(C(=O)O)c2ccccc21.NCC12CCCN(CCC1)C2 | O=C(NCC12CCCN(CCC1)C2)c1c[nH]c2ccccc12 | null | null | CO.C(Cl)Cl.O1CCCC1 | Acylation | OtherReaction | bc16af2d4a965c15729fe77d296d53d42b81335eb8cb47aa1eea0c3f040c41cc | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCC12CCCN(CCC1)C2)c1c[nH]c2ccccc12 | C-[n;H0;D3;+0:1]1:[c:2]:[c:3](-[C;H0;D3;+0:4](-O)=[O;D1;H0:5]):[c:6]:[c:7]:1:[c:8].[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:3]1:[c:2]:[nH;D2;+0:1]:[c:7](:[c:8]):[c:6]:1 | 79.6 | [{"value": 76.0, "product": "N12CCCC(CCC1)(C2)CNC(=O)C2=CNC1=CC=CC=C21", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.6, "product": "N12CCCC(CCC1)(C2)CNC(=O)C2=CNC1=CC=CC=C21", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | A solution of 1-methyl-1H-indole-3-carboxylic acid (1.53 g, 8.7 mmol) in anhydrous tetrahydrofuran (8 mL) under nitrogen was treated with 1.49 g (9.2 mmol) of 1,1'-carbonyldiimidazole (CDI) and stirred for 10 minutes. At this point a thick suspension formed, and anhydrous N,N-dimethylformamide (8 mL) was added. After a... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | c1c[nH]c2ccccc12 | c1ccc2[nH]ccc2c1 | C1CC2CCCN(C1)C2.c1ccc2[nH]ccc2c1 | HO- | CO.C(Cl)Cl.O1CCCC1 | null | 0.166667 | Cn1cc(C(=O)O)c2ccccc21.NCC12CCCN(CCC1)C2>CO.C(Cl)Cl.O1CCCC1>O=C(NCC12CCCN(CCC1)C2)c1c[nH]c2ccccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-249065f6497c4fd0a7b024f92416e2ba | COc1cc(N)c(Cl)cc1C(=O)O.OCC12CCCN(CC1)C2>>COc1cc(N)c(Cl)cc1C(=O)OCC12CCCN(CC1)C2 | C(CCC)[Li].CCCCCC.N12CCCC(CC1)(C2)CO.NC1=CC(=C(C(=O)O)C=C1Cl)OC.C(=O)(N1C=NC=C1)N1C=NC=C1>>N12CCCC(CC1)(C2)COC(C2=C(C=C(C(=C2)Cl)N)OC)=O | O[C:11]([c:10]1[c:3]([O:2][CH3:1])[cH:4][c:5]([NH2:6])[c:7]([Cl:8])[cH:9]1)=[O:12].[OH:13][CH2:14][C:15]12[CH2:16][CH2:17][CH2:18][N:19]([CH2:20][CH2:21]1)[CH2:22]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[c:7]([Cl:8])[cH:9][c:10]1[C:11](=[O:12])[O:13][CH2:14][C:15]12[CH2:16][CH2:17][CH2:18][N:19]([CH2:20][CH2:21]1)[CH2... | COc1cc(N)c(Cl)cc1C(=O)O.OCC12CCCN(CC1)C2 | COc1cc(N)c(Cl)cc1C(=O)OCC12CCCN(CC1)C2 | null | null | O1CCCC1 | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | O=C(OCC12CCCN(CC1)C2)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 47.3 | [{"value": 47.0, "product": "N12CCCC(CC1)(C2)COC(C2=C(C=C(C(=C2)Cl)N)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.3, "product": "N12CCCC(CC1)(C2)COC(C2=C(C=C(C(=C2)Cl)N)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 4-amino-5-chloro-2-methoxybenzoic acid (1.62 g, 8.0 mmol) in anhydrous tetrahydrofuran (10 mL) under nitrogen was treated with 1,1'-carbonyldiimidazole (1.38 g, 8.5 mmol), stirred one hour, and degassed under a stream of nitrogen over 10 minutes. Meanwhile, a cooled (-10° C.) solution of 1-azabicyclo[3.2.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1.C1CC2CCN(C1)C2 | HO- | O1CCCC1 | null | 1 | COc1cc(N)c(Cl)cc1C(=O)O.OCC12CCCN(CC1)C2>O1CCCC1>COc1cc(N)c(Cl)cc1C(=O)OCC12CCCN(CC1)C2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6541df2d7c0d4d2fa50faf847fad032f | O=C(O)c1c[nH]c2ccccc12.OCC12CCCN(CC1)C2>>O=C(OCC12CCCN(CC1)C2)c1c[nH]c2ccccc12 | C(CCC)[Li].CCCCCC.N12CCCC(CC1)(C2)CO.N1C=C(C2=CC=CC=C12)C(=O)O.C(=O)(N1C=NC=C1)N1C=NC=C1>>N12CCCC(CC1)(C2)COC(=O)C2=CNC1=CC=CC=C21 | O[C:2](=[O:1])[c:13]1[cH:14][nH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12.[OH:3][CH2:4][C:5]12[CH2:6][CH2:7][CH2:8][N:9]([CH2:10][CH2:11]1)[CH2:12]2>>[O:1]=[C:2]([O:3][CH2:4][C:5]12[CH2:6][CH2:7][CH2:8][N:9]([CH2:10][CH2:11]1)[CH2:12]2)[c:13]1[cH:14][nH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12 | O=C(O)c1c[nH]c2ccccc12.OCC12CCCN(CC1)C2 | O=C(OCC12CCCN(CC1)C2)c1c[nH]c2ccccc12 | null | null | O1CCCC1 | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | O=C(OCC12CCCN(CC1)C2)c1c[nH]c2ccccc12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[c:7]:1.[C:8]-[C:9]-[OH;D1;+0:10]>>[C:8]-[C:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[c:7]:1 | 52.4 | [{"value": 52.0, "product": "N12CCCC(CC1)(C2)COC(=O)C2=CNC1=CC=CC=C21", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.4, "product": "N12CCCC(CC1)(C2)COC(=O)C2=CNC1=CC=CC=C21", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of indole-3-carboxylic acid (1.45 g, 9 mmol) in anhydrous tetrahydrofuran (10 mL) under nitrogen was treated with 1,1'-carbonyldiimidazole (1.53 g, 9.4 mmol), stirred for one hour, and degassed with a stream of nitrogen over 10 minutes. Meanwhile, a cooled (-10° C.) solution of 1-azabicyclo[3.2.1]octane-5-me... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | C1CC2CCN(C1)C2.c1ccc2[nH]ccc2c1 | HO- | O1CCCC1 | null | 1 | O=C(O)c1c[nH]c2ccccc12.OCC12CCCN(CC1)C2>O1CCCC1>O=C(OCC12CCCN(CC1)C2)c1c[nH]c2ccccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a25b2cb2221d43fab68ec429840ec1e6 | Cn1cc(C(=O)O)c2ccccc21.OCC12CCCN(CC1)C2>>Cn1cc(C(=O)OCC23CCCN(CC2)C3)c2ccccc21 | C(CCC)[Li].CCCCCC.N12CCCC(CC1)(C2)CO.CN1C=C(C2=CC=CC=C12)C(=O)O.C(=O)(N1C=NC=C1)N1C=NC=C1>>N12CCCC(CC1)(C2)COC(=O)C2=CN(C1=CC=CC=C21)C | O[C:5]([c:4]1[cH:3][n:2]([CH3:1])[c:22]2[c:17]1[cH:18][cH:19][cH:20][cH:21]2)=[O:6].[OH:7][CH2:8][C:9]12[CH2:10][CH2:11][CH2:12][N:13]([CH2:14][CH2:15]1)[CH2:16]2>>[CH3:1][n:2]1[cH:3][c:4]([C:5](=[O:6])[O:7][CH2:8][C:9]23[CH2:10][CH2:11][CH2:12][N:13]([CH2:14][CH2:15]2)[CH2:16]3)[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22... | Cn1cc(C(=O)O)c2ccccc21.OCC12CCCN(CC1)C2 | Cn1cc(C(=O)OCC23CCCN(CC2)C3)c2ccccc21 | null | null | O1CCCC1 | Acylation | Esterification of Carboxylic Acids | d9bd78214ee7dbc907e499722ae01849a72d188753963443e5df9fe42c31c43b | 3652e761944e8ef7ee40675a156c8ae39909c72166786934d88652debf2ec1ac | O=C(OCC12CCCN(CC1)C2)c1c[nH]c2ccccc12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6](-[C;D1;H3:7]):[c:8]:1.[C:9]-[C:10]-[OH;D1;+0:11]>>[C:9]-[C:10]-[O;H0;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6](-[C;D1;H3:7]):[c:8]:1 | 58 | [{"value": 58.0, "product": "N12CCCC(CC1)(C2)COC(=O)C2=CN(C1=CC=CC=C21)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.6, "product": "N12CCCC(CC1)(C2)COC(=O)C2=CN(C1=CC=CC=C21)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 1-methyl-1H-indole-3-carboxylic acid (1.75 g, 10 mmol) in anhydrous tetrahydrofuran (10 mL) under nitrogen was treated with 1,1'-carbonyldiimidazole (1.79 g, 11 mmol), stirred for one hour, and degassed under a stream of nitrogen over 10 minutes. Meanwhile a cooled (-10° C.) solution of 1-azabicyclo[3.2.1... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | C1CC2CCN(C1)C2.c1c[nH]c2ccccc12 | HO- | O1CCCC1 | null | 1 | Cn1cc(C(=O)O)c2ccccc21.OCC12CCCN(CC1)C2>O1CCCC1>Cn1cc(C(=O)OCC23CCCN(CC2)C3)c2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9f608317b9754efda2c9e04eca249eb4 | COc1cc(N)c(Cl)cc1C(=O)O.OCC12CCCN(CCC1)C2>>COc1cc(N)c(Cl)cc1C(=O)OCC12CCCN(CCC1)C2 | C(CCC)[Li].CCCCCC.N12CCCC(CCC1)(C2)CO.NC1=CC(=C(C(=O)O)C=C1Cl)OC.C(=O)(N1C=NC=C1)N1C=NC=C1>>N12CCCC(CCC1)(C2)COC(C2=C(C=C(C(=C2)Cl)N)OC)=O | O[C:11]([c:10]1[c:3]([O:2][CH3:1])[cH:4][c:5]([NH2:6])[c:7]([Cl:8])[cH:9]1)=[O:12].[OH:13][CH2:14][C:15]12[CH2:16][CH2:17][CH2:18][N:19]([CH2:20][CH2:21][CH2:22]1)[CH2:23]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[c:7]([Cl:8])[cH:9][c:10]1[C:11](=[O:12])[O:13][CH2:14][C:15]12[CH2:16][CH2:17][CH2:18][N:19]([CH2:20][CH2:2... | COc1cc(N)c(Cl)cc1C(=O)O.OCC12CCCN(CCC1)C2 | COc1cc(N)c(Cl)cc1C(=O)OCC12CCCN(CCC1)C2 | null | null | O1CCCC1 | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | O=C(OCC12CCCN(CCC1)C2)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 57.3 | [{"value": 57.0, "product": "N12CCCC(CCC1)(C2)COC(C2=C(C=C(C(=C2)Cl)N)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.3, "product": "N12CCCC(CCC1)(C2)COC(C2=C(C=C(C(=C2)Cl)N)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 4-amino-5-chloro-2-methoxybenzoic acid (2.02 g, 10 mmol) in anhydrous tetrahydrofuran (10 mL) under nitrogen was treated with 1,1'-carbonyldiimidazole (1.70 g, 10.5 mmol), stirred for one hour, then degassed with a stream of nitrogen over 10 minutes. Meanwhile, a cooled (-10° C.) solution of 1-azabicyclo[... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1.C1CC2CCCN(C1)C2 | HO- | O1CCCC1 | null | 1 | COc1cc(N)c(Cl)cc1C(=O)O.OCC12CCCN(CCC1)C2>O1CCCC1>COc1cc(N)c(Cl)cc1C(=O)OCC12CCCN(CCC1)C2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-805756e25c6e47c98a7e9f3b4a6eca54 | O=C(O)c1c[nH]c2ccccc12.OCC12CCCN(CCC1)C2>>O=C(OCC12CCCN(CCC1)C2)c1c[nH]c2ccccc12 | C(CCC)[Li].CCCCCC.N12CCCC(CCC1)(C2)CO.N1C=C(C2=CC=CC=C12)C(=O)O.C(=O)(N1C=NC=C1)N1C=NC=C1>>N12CCCC(CCC1)(C2)COC(=O)C2=CNC1=CC=CC=C21 | O[C:2](=[O:1])[c:14]1[cH:15][nH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12.[OH:3][CH2:4][C:5]12[CH2:6][CH2:7][CH2:8][N:9]([CH2:10][CH2:11][CH2:12]1)[CH2:13]2>>[O:1]=[C:2]([O:3][CH2:4][C:5]12[CH2:6][CH2:7][CH2:8][N:9]([CH2:10][CH2:11][CH2:12]1)[CH2:13]2)[c:14]1[cH:15][nH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]1... | O=C(O)c1c[nH]c2ccccc12.OCC12CCCN(CCC1)C2 | O=C(OCC12CCCN(CCC1)C2)c1c[nH]c2ccccc12 | null | null | O1CCCC1 | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | O=C(OCC12CCCN(CCC1)C2)c1c[nH]c2ccccc12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[c:7]:1.[C:8]-[C:9]-[OH;D1;+0:10]>>[C:8]-[C:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[c:7]:1 | 60 | [{"value": 60.0, "product": "N12CCCC(CCC1)(C2)COC(=O)C2=CNC1=CC=CC=C21", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.0, "product": "N12CCCC(CCC1)(C2)COC(=O)C2=CNC1=CC=CC=C21", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of indole-3-carboxylic acid (1.62 g, 10 mmol) in anhydrous tetrahydrofuran (10 mL) under nitrogen was treated with 1,1'-carbonyldiimidazole (1.70 g, 10.5 mmol), stirred for one hour, and degassed with a stream of nitrogen for 10 minutes giving a suspension. Meanwhile, a cooled (-10° C.) solution of 1-azabicy... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | C1CC2CCCN(C1)C2.c1ccc2[nH]ccc2c1 | HO- | O1CCCC1 | null | 1 | O=C(O)c1c[nH]c2ccccc12.OCC12CCCN(CCC1)C2>O1CCCC1>O=C(OCC12CCCN(CCC1)C2)c1c[nH]c2ccccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4406e0402c004a7288caf0b804f30d30 | Cn1nc(C(=O)N2C=CNC2)c2ccccc21.OCC12CCCN(CC1)C2>>Cn1nc(C(=O)OCC23CCCN(CC2)C3)c2ccccc21 | N12CCCC(CC1)(C2)CO.C(CCC)[Li].CCCCCC.N1(CNC=C1)C(=O)C1=NN(C2=CC=CC=C12)C>>N12CCCC(CC1)(C2)COC(=O)C2=NN(C1=CC=CC=C21)C | C1=CN([C:5]([c:4]2[n:3][n:2]([CH3:1])[c:22]3[c:17]2[cH:18][cH:19][cH:20][cH:21]3)=[O:6])CN1.[OH:7][CH2:8][C:9]12[CH2:10][CH2:11][CH2:12][N:13]([CH2:14][CH2:15]1)[CH2:16]2>>[CH3:1][n:2]1[n:3][c:4]([C:5](=[O:6])[O:7][CH2:8][C:9]23[CH2:10][CH2:11][CH2:12][N:13]([CH2:14][CH2:15]2)[CH2:16]3)[c:17]2[cH:18][cH:19][cH:20][cH:2... | Cn1nc(C(=O)N2C=CNC2)c2ccccc21.OCC12CCCN(CC1)C2 | Cn1nc(C(=O)OCC23CCCN(CC2)C3)c2ccccc21 | null | null | O1CCCC1 | Acylation | OtherReaction | 8edc29c6893178a6858d8b5ac545e0fdd2b118e1fbf01c3899745cd412374b17 | 0b63fdab604c55d4e8e6de999528c93d919889391aba78782e3e6672485adf50 | O=C(OCC12CCCN(CC1)C2)c1n[nH]c2ccccc12 | [C;D1;H3:1]-[#7;a:2]1:[#7;a:3]:[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-N2-C-N-C=C-2):[c:7]:[c:8]:1.[C:9]-[C:10]-[OH;D1;+0:11]>>[C:9]-[C:10]-[O;H0;D2;+0:11]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c:4]1:[#7;a:3]:[#7;a:2](-[C;D1;H3:1]):[c:8]:[c:7]:1 | 53.1 | [{"value": 53.0, "product": "N12CCCC(CC1)(C2)COC(=O)C2=NN(C1=CC=CC=C21)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.1, "product": "N12CCCC(CC1)(C2)COC(=O)C2=NN(C1=CC=CC=C21)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A cooled (0° C.) solution of 1-azabicyclo[3.2.1]oct-5-ylmethanol (1.70 g, 12 mmol) in anhydrous tetrahydrofuran (15 mL) under nitrogen was treated (via syringe) with 2.45N n-butyllithium/hexane (12 mmol), then stirred at room temperature for thirty minutes and concentrated in vacuo to remove all hexane. Anhydrous tetra... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Enamine.Tertiary amide.Primary alcohol | Ester | C1=CNCN1 | null | C1CC2CCN(C1)C2.c1n[nH]c2ccccc12 | Other | O1CCCC1 | null | 3 | Cn1nc(C(=O)N2C=CNC2)c2ccccc21.OCC12CCCN(CC1)C2>O1CCCC1>Cn1nc(C(=O)OCC23CCCN(CC2)C3)c2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1339d8a661144dc8b56716544887dca6 | C=CCOc1cc(N)c(Cl)cc1C(=O)O.NCC12CCCN(CC1)C2>>C=CCOc1cc(N)c(Cl)cc1C(=O)NCC12CCCN(CC1)C2 | NC1=CC(=C(C(=O)O)C=C1Cl)OCC=C.N12CCCC(CC1)(C2)CN>>NC1=CC(=C(C(=O)NCC23CCCN(CC2)C3)C=C1Cl)OCC=C | O[C:13]([c:12]1[c:5]([O:4][CH2:3][CH:2]=[CH2:1])[cH:6][c:7]([NH2:8])[c:9]([Cl:10])[cH:11]1)=[O:14].[NH2:15][CH2:16][C:17]12[CH2:18][CH2:19][CH2:20][N:21]([CH2:22][CH2:23]1)[CH2:24]2>>[CH2:1]=[CH:2][CH2:3][O:4][c:5]1[cH:6][c:7]([NH2:8])[c:9]([Cl:10])[cH:11][c:12]1[C:13](=[O:14])[NH:15][CH2:16][C:17]12[CH2:18][CH2:19][CH... | C=CCOc1cc(N)c(Cl)cc1C(=O)O.NCC12CCCN(CC1)C2 | C=CCOc1cc(N)c(Cl)cc1C(=O)NCC12CCCN(CC1)C2 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCC12CCCN(CC1)C2)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Following the procedure of Example 1, the title compound is prepared from 4-amino-5-chloro-2-(2-propenyloxy)benzoic acid and 1-azabicyclo[3.2.1]octan-5-methanamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC2CCN(C1)C2 | HO- | null | null | null | C=CCOc1cc(N)c(Cl)cc1C(=O)O.NCC12CCCN(CC1)C2>>C=CCOc1cc(N)c(Cl)cc1C(=O)NCC12CCCN(CC1)C2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e3905ec671db4476912df221b80d4a05 | CCOC(=O)C=[N+]=[N-].O=C1CCCCCCC1>>CCOC(=O)C1CCCCCCCC1=O | C1(CCCCCCC1)=O.F[B-](F)(F)F.C(C)[O+](CC)CC.[N+](=[N-])=CC(=O)OCC>>C(C)OC(=O)C1C(CCCCCCC1)=O | [N-]=[N+]=[CH:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[CH2:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1=[O:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1=[O:15] | CCOC(=O)C=[N+]=[N-].O=C1CCCCCCC1 | CCOC(=O)C1CCCCCCCC1=O | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | f4358bd2f3aee366b34c2d0a955f09f77d20286ffd3a4c0291e733957f7927ad | 4f5428734ef204d1fb311ee2d76e19b4e3b64154d65d22fa6a8abd7ae101915a | O=C1CCCCCCCC1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D2;+0:5]=[N+]=[N-].[C:6]-[C:7]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[CH2;D2;+0:10]-[C:11]-[C:12]>>[C:6]-[C:7]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[CH;D3;+0:5](-[C:3](=[O;D1;H0:4])-[#8:2]-[C:1])-[CH2;D2;+0:10]-[C:11]-[C:12] | null | [] | 0 | CELSIUS | 4 | HOUR | Cyclooctanone (25 g, 198 mmol) is dissolved in methylene chloride (500 mL) and the solution is cooled to 0° C. Triethyloxonium tetrafluoroborate (121.6 g, 640 mmol) is added. Ethyl diazoacetate (41.61 g, 365 mmol) is then added dropwise over 25 minutes, and the reaction is stirred at 0° C. for 4 hours. The reaction is ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Diazo | Ketone.Ester | C1CCCCCCC1 | C1CCCCCCCC1 | C1CCCCCCCC1 | Other | C(Cl)Cl | 0 | 4 | CCOC(=O)C=[N+]=[N-].O=C1CCCCCCC1>C(Cl)Cl>CCOC(=O)C1CCCCCCCC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-457a83af2b8e486aa8de7028583f3486 | CCOC(=O)C1CCCCCCCC1=O.[NH4+]>>CCOC(=O)C1CCCCCCCC(=O)N1 | [OH-].[NH4+].CS(=O)(=O)O.C(C)OC(=O)C1C(CCCCCCC1)=O.[N-]=[N+]=[N-].[Na+]>>O=C1NC(CCCCCCC1)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1=[O:15].[NH4+:16]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[O:15])[NH:16]1 | CCOC(=O)C1CCCCCCCC1=O.[NH4+] | CCOC(=O)C1CCCCCCCC(=O)N1 | null | null | C(Cl)(Cl)Cl | Functional Group Addition | OtherReaction | dab08ea5b22dba23d2341d507cac6bea4785139ff0bce40600f0aa70079110c9 | 579fa31aaf6029bc11db649a382a0ef8bdbfe77711c459bfaf065d9de2dbfbb7 | O=C1CCCCCCCCN1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[CH;D3;+0:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9])-[C:10]-[C:11].[NH4+;D0:12]>>[C:1]-[C:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[NH;D2;+0:12]-[CH;D3;+0:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9])-[C:10]-[C:11] | null | [] | 0 | CELSIUS | 30 | MINUTE | 2-Ethoxycarbonyl-cyclononanone (13.72 g, 64.7 mmol) is dissolved in chloroform (200 mL) and cooled to 0° C. Methanesulfonic acid (62.4 g, 650 mmol) is added, followed by sodium azide (12.68 g, 195 mmol). The reaction is stirred at room temperature for 30 minutes, and then heated to reflux for 4 hours. The reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ester.Secondary amide | C1CCCCCCCC1 | C1CCCCNCCCC1 | C1CCCCNCCCC1 | null | C(Cl)(Cl)Cl | 0 | 0.5 | CCOC(=O)C1CCCCCCCC1=O.[NH4+]>C(Cl)(Cl)Cl>CCOC(=O)C1CCCCCCCC(=O)N1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-506b9adb631a461cb9ffccba8d2f7bb0 | BrBr.CCOC(=O)C1CCCCCCCC(=O)N1>>CCOC(=O)[C@@H]1CCCCCC[C@H](Br)C(=O)N1 | BrBr.P(Cl)(Cl)(Cl)(Cl)Cl.II.O=C1NC(CCCCCCC1)C(=O)OCC>>Br[C@@H]1C(N[C@@H](CCCCCC1)C(=O)OCC)=O | Br[Br:14].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:15](=[O:16])[NH:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C@@H:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([Br:14])[C:15](=[O:16])[NH:17]1 | BrBr.CCOC(=O)C1CCCCCCCC(=O)N1 | CCOC(=O)[C@@H]1CCCCCC[C@H](Br)C(=O)N1 | null | null | C(Cl)Cl | Functional Group Interconversion | Bromination | 0eec1c7220b5e11cd6f23f5cad283ea61e0679382fe547aa2e4e5e76415cfb6a | 0c353a1260488c22c3ffb72de5623420c3ec35470a0b3a2045b11c29224f458e | O=C1CCCCCCCCN1 | Br-[Br;H0;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]-[#7:6]-[C:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[C:10]-[C:11]>>[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]-[#7:6]-[C:7](=[O;D1;H0:8])-[C@@H;D3;+0:9](-[Br;H0;D1;+0:1])-[C:10]-[C:11] | null | [] | 0 | CELSIUS | 15 | MINUTE | Ethyl 2-oxo-1-azacyclodecane-10-carboxylate (4.0 g, 17.6 mmol) is dissolved in methylene chloride (50 mL), and cooled to 0° C. Phosphorus pentachloride (3.85 g, 18.5 mmol) and iodine (0.051 g, 0.2 mmol) are added. The reaction is stirred for 15 minutes at 0° C. Then, bromine (3.10 g, 19.4 mmol) is added, and the reacti... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary halide | C1CCCCNCCCC1 | C1CCCCNCCCC1 | C1CCCCNCCCC1 | HBr | C(Cl)Cl | 0 | 0.25 | BrBr.CCOC(=O)C1CCCCCCCC(=O)N1>C(Cl)Cl>CCOC(=O)[C@@H]1CCCCCC[C@H](Br)C(=O)N1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-dcb68cc3bff744d997cc097884f62d34 | CCOC(=O)[C@@H]1CCCCCC[C@H](Br)C(=O)N1>>CCOC(=O)[C@@H]1CCCCCC[C@H](OC(C)=O)C(=O)N1 | Br[C@@H]1C(N[C@@H](CCCCCC1)C(=O)OCC)=O>>C(C)(=O)O[C@@H]1C(N[C@@H](CCCCCC1)C(=O)OCC)=O | Br[C@H:13]1[CH2:12][CH2:11][CH2:10][CH2:1][CH2:8][CH2:7][C@@H:6]([C:4](=[O:3])[O:14][CH2:15][CH3:16])[NH:20][C:18]1=[O:19]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C@@H:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([O:14][C:15]([CH3:16])=[O:17])[C:18](=[O:19])[NH:20]1 | CCOC(=O)[C@@H]1CCCCCC[C@H](Br)C(=O)N1 | CCOC(=O)[C@@H]1CCCCCC[C@H](OC(C)=O)C(=O)N1 | null | C(C)(=O)[O-].[Ag+] | CN(C=O)C.C(C)(=O)OCC | Miscellaneous | OtherReaction | 13d89ff76626018539378bea9b2dd36c53f4d944ec29433c9578ce63d5256397 | 6525c54fe846f0fa59c15bd6b671acee5a1b77633e0eba0e10f45d27e96ae1f5 | O=C1CCCCCCCCN1 | Br-[C@H;D3;+0:1]1-[C:2]-[C:3]-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[C:7]-[C:8](-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[O;H0;D2;+0:11]-[CH2;D2;+0:12]-[C;D1;H3:13])-[#7:14]-[C:15]-1=[O;D1;H0:16]>>[C;D1;H3:13]-[C;H0;D3;+0:12](=[O;D1;H0:17])-[O;H0;D2;+0:11]-[C@H;D3;+0:1]1-[C:2]-[C:3]-[CH2;D2;+0:4]-[C:18]-[CH2;D2;+0:6]-[C:7... | null | [] | 100 | CELSIUS | null | null | Cis ethyl 3-bromo-2-oxo-1-azacyclodecane-10-carboxylate (2.96 g, 9.67 mmol) is dissolved in dimethylformamide (30 mL). Silver acetate (6.35 g, 38 mmol) is added, and the reaction is heated to 100° C. for 3 hours. After cooling back to room temperature, the reaction is diluted with ethyl acetate (100 mL), filtered throu... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester | Ester.Ester | C1CCCCNCCCC1 | C1CCCCNCCCC1 | C1CCCCNCCCC1 | Br- | C(C)(=O)[O-].[Ag+].CN(C=O)C.C(C)(=O)OCC | 100 | null | CCOC(=O)[C@@H]1CCCCCC[C@H](Br)C(=O)N1>C(C)(=O)[O-].[Ag+].CN(C=O)C.C(C)(=O)OCC>CCOC(=O)[C@@H]1CCCCCC[C@H](OC(C)=O)C(=O)N1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d4fb9e46ad954be7a349fa818cd8a137 | CCOC(=O)C1CCCCCCC(=O)C(=O)N1.C[Si](C)(C)[CH2][Mg][Cl]>>CCOC(=O)C1CCCCCCC(O)(C[Si](C)(C)C)C(=O)N1 | C[Si](C)(C)C[Mg]Cl.O=C1NC(CCCCCCC1=O)C(=O)OCC>>C[Si](C)(C)CC1(C(NC(CCCCCC1)C(=O)OCC)=O)O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](=[O:14])[C:20](=[O:21])[NH:22]1.[Cl][Mg][CH2:15][Si:16]([CH3:17])([CH3:18])[CH3:19]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:14])([CH2:15][Si:16]([CH3:17])([CH3:18])[CH3:19])... | CCOC(=O)C1CCCCCCC(=O)C(=O)N1.C[Si](C)(C)[CH2][Mg][Cl] | CCOC(=O)C1CCCCCCC(O)(C[Si](C)(C)C)C(=O)N1 | null | null | CCOCC | C-C Coupling | Grignard from ketone to alcohol | 5f5e7255c18c21fef298467b179ec1f4f56424d16c6fc1d165c33612b9c843be | 5854166cd4ea706bc07d74dc79eb8f4a990bc6c5eacbf0ca947d88ee86e78fdf | O=C1CCCCCCCCN1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7:5]-[C:6](=[O;D1;H0:7])-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[C:10]-[C:11].[C;D1;H3:12]-[#14:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[CH2;D2;+0:16]-[Mg]-[Cl]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7:5]-[C:6](=[O;D1;H0:7])-[C;H0;D4;+0:8](-[OH;D1;+0:9])(-[CH2;D2;+0:16]-[#14:13](-[C;D1;H3:12])(-[C;D1... | null | [] | 0 | CELSIUS | 20 | MINUTE | Ethyl 2,3-di-oxo-1-azacyclodecane-10-carboxylate (5.02 g, 20.81 mmol) is dissolved in ether (50 mL), and cooled to 0° C. Trimethylsilylmethylmagnesium chloride (42.0 mL of a 1.0M solution in ether, 42.0 mmol) is added dropwise, the reaction is stirred at 0° C. for 20 minutes, and then heated to reflux overnight. The re... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ketone | Tertiary alcohol | C1CCCCNCCCC1 | C1CCCCNCCCC1 | C1CCCCNCCCC1 | Mg | CCOCC | 0 | 0.333333 | CCOC(=O)C1CCCCCCC(=O)C(=O)N1.C[Si](C)(C)[CH2][Mg][Cl]>CCOCC>CCOC(=O)C1CCCCCCC(O)(C[Si](C)(C)C)C(=O)N1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-33f9adfd6f284316b20090b99cc163ce | CCOC(=O)C1CCCCCCC(O)(C[Si](C)(C)C)C(=O)N1>>C=C1CCCCCCC(C(=O)OCC)NC1=O | C[Si](C)(C)CC1(C(NC(CCCCCC1)C(=O)OCC)=O)O.B(F)(F)F.CCOCC>>C=C1C(NC(CCCCCC1)C(=O)OCC)=O | C[Si](C)(C)[CH2:1][C:2]1(O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]([C:10](=[O:11])[O:12][CH2:13][CH3:14])[NH:15][C:16]1=[O:17]>>[CH2:1]=[C:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]([C:10](=[O:11])[O:12][CH2:13][CH3:14])[NH:15][C:16]1=[O:17] | CCOC(=O)C1CCCCCCC(O)(C[Si](C)(C)C)C(=O)N1 | C=C1CCCCCCC(C(=O)OCC)NC1=O | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 08ed58de1dbc0a0a0052264d5574865af5675238cbdaadd8f99b21f9961cf196 | 70726fffd1247b98d91d1ce6bd15a8de9817aaf84343b50627ddafec4dfb3c6c | C=C1CCCCCCCNC1=O | C-[Si](-C)(-C)-[CH2;D2;+0:1]-[C;H0;D4;+0:2](-O)(-[C:3]-[C:4])-[C:5](=[O;D1;H0:6])-[#7:7]-[C:8]-[C:9](-[#8:10])=[O;D1;H0:11]>>[#8:10]-[C:9](=[O;D1;H0:11])-[C:8]-[#7:7]-[C:5](=[O;D1;H0:6])-[C;H0;D3;+0:2](=[CH2;D1;+0:1])-[C:3]-[C:4] | null | [] | null | null | 26 | HOUR | Ethyl 3-(trimethylsilylmethyl)-3-hydroxy-2-oxo-1-azacyclodecane-10-carboxylate (0.98 g, 2.98 mmol) is dissolved in methylene chloride (50 mL), and boron trifluoride etherate (1.8 mL, 15 mmol) is added. The reaction is stirred at room temperature for 26 hours. The reaction is then quenched with saturated ammonium chlori... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol.Silyl protective group | Vinyl | C1CCCCNCCCC1 | C1CCCCNCCCC1 | C1CCCCNCCCC1 | HO- | C(Cl)Cl | null | 26 | CCOC(=O)C1CCCCCCC(O)(C[Si](C)(C)C)C(=O)N1>C(Cl)Cl>C=C1CCCCCCC(C(=O)OCC)NC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0675e965fa4340e2acbd5041468c8136 | CC(=O)Cl.O=C1N[C@@H](C(=O)O)CCCCCC[C@@H]1CS>>CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)O)NC1=O | SC[C@@H]1C(N[C@H](CCCCCC1)C(=O)O)=O.C(C)(=O)Cl>>C(C)(=O)SC[C@@H]1C(N[C@H](CCCCCC1)C(=O)O)=O | Cl[C:2]([CH3:1])=[O:3].[SH:4][CH2:5][C@H:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([C:14](=[O:15])[OH:16])[NH:17][C:18]1=[O:19]>>[CH3:1][C:2](=[O:3])[S:4][CH2:5][C@H:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([C:14](=[O:15])[OH:16])[NH:17][C:18]1=[O:19] | CC(=O)Cl.O=C1N[C@@H](C(=O)O)CCCCCC[C@@H]1CS | CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)O)NC1=O | null | null | N1=CC=CC=C1 | Acylation | thioether_nucl_sub | 774e8f449f87493fdbd93fdbbfef7c7bc086966dfce8806abcb487630046ef59 | cf70b55890699bc889b230d5ae9783daf8be8d20d1ad4c06197ffaf659088f4e | O=C1CCCCCCCCN1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7:4]-[C:5](=[O;D1;H0:6])-[C:7]-[C:8]-[SH;D1;+0:9]>>[#7:4]-[C:5](=[O;D1;H0:6])-[C:7]-[C:8]-[S;H0;D2;+0:9]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | null | [] | null | null | 8 | HOUR | Trans 3-mercaptomethyl-2-oxo-1-azacyclodecane-10-carboxylic acid (0.75 g, 3.06 mmol) is dissolved in pyridine (20 mL). Acetyl chloride (0.26 g, 3.37 mmol) is added, and the reaction is stirred at room temperature overnight. The reaction is quenched by cooling to 0° C., adding concentrated hydrochloric acid (20 mL), dil... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aliphatic thiol | Carbo-thioester | null | null | C1CCCCNCCCC1 | HCl | N1=CC=CC=C1 | null | 8 | CC(=O)Cl.O=C1N[C@@H](C(=O)O)CCCCCC[C@@H]1CS>N1=CC=CC=C1>CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)O)NC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6d7f78a9e4854515844933e38954e2d1 | CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)O)NC1=O>>CC(=O)SC[C@H]1CCCCCC[C@H](C(N)=O)NC1=O | C(C)(=O)SC[C@@H]1C(N[C@H](CCCCCC1)C(=O)O)=O.CN1CCOCC1.ClC(=O)OCC>>C(C)(=O)SC[C@@H]1C(N[C@H](CCCCCC1)C(=O)N)=O | O[C:14]([C@H:13]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]([CH2:5][S:4][C:2]([CH3:1])=[O:3])[C:18](=[O:19])[NH:17]1)=[O:16]>>[CH3:1][C:2](=[O:3])[S:4][CH2:5][C@H:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([C:14]([NH2:15])=[O:16])[NH:17][C:18]1=[O:19] | CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)O)NC1=O | CC(=O)SC[C@H]1CCCCCC[C@H](C(N)=O)NC1=O | null | null | C(Cl)Cl.O1CCCC1 | Functional Group Interconversion | OtherReaction | e1b1a1f71ee10336b9e90a021457b106dbfe08a22161aaad6804675a8134a46f | 5d384be3554a01fd49be5eb779c3b10075a4cc9a2373eb20aaa867286d4e28a9 | O=C1CCCCCCCCN1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7]>>[C:4]-[C:3](-[C;H0;D3;+0:1](-[N;D1;H2:8])=[O;D1;H0:2])-[#7:5]-[C:6]=[O;D1;H0:7] | null | [] | -20 | CELSIUS | 30 | MINUTE | Trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid (0.30 g, 1.05 mmol) is dissolved in tetrahydrofuran (5.0 mL). 4-Methylmorpholine (0.14 mL, 1.05 mmol) is then added, and the reaction is cooled to -20° C. Ethyl chloroformate (0.1 mL, 1.05 mmol) is then added, and the reaction is stirred at -20° C. fo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | C1CCCCNCCCC1 | null | C(Cl)Cl.O1CCCC1 | -20 | 0.5 | CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)O)NC1=O>C(Cl)Cl.O1CCCC1>CC(=O)SC[C@H]1CCCCCC[C@H](C(N)=O)NC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b118b628f60746c29335fc3e59194550 | CC(=O)SC[C@H]1CCCCCC[C@H](C(N)=O)NC1=O>>NC(=O)[C@H]1CCCCCC[C@H](CS)C(=O)N1 | C(C)(=O)SC[C@@H]1C(N[C@H](CCCCCC1)C(=O)N)=O.[OH-].[Na+].Cl>>SC[C@@H]1C(N[C@H](CCCCCC1)C(=O)N)=O | CC(=O)[S:13][CH2:12][C@H:11]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]([C:2]([NH2:1])=[O:3])[NH:16][C:14]1=[O:15]>>[NH2:1][C:2](=[O:3])[C@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C@H:11]([CH2:12][SH:13])[C:14](=[O:15])[NH:16]1 | CC(=O)SC[C@H]1CCCCCC[C@H](C(N)=O)NC1=O | NC(=O)[C@H]1CCCCCC[C@H](CS)C(=O)N1 | null | null | C(C)O | Reduction | OtherReaction | 7702cd666d5d9a9f1bdea3600e3b84cc62dd11d3f2cea261702317a39db4e581 | 18d802456fe85193570fdb3a00b25c8956a03b5a0210f708f961e42c1669d76e | O=C1CCCCCCCCN1 | C-C(=O)-[S;H0;D2;+0:1]-[C:2]-[C:3]-[C:4](=[O;D1;H0:5])-[#7:6]>>[#7:6]-[C:4](=[O;D1;H0:5])-[C:3]-[C:2]-[SH;D1;+0:1] | null | [] | null | null | 1 | HOUR | Trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxamide (0.16 g, 0.56 mmol) is dissolved in ethanol (5.0 mL). An aqueous solution of 1N sodium hydroxide (0.60 mL, 0.60 mmol) is added, and the reaction is stirred for 1 hour. The reaction is acidified with 1N hydrochloric acid to a pH of about 3, and the solvent... | 10.6084/m9.figshare.5104873.v1 | null | Carbo-thioester | Aliphatic thiol | null | null | C1CCCCNCCCC1 | HO- | C(C)O | null | 1 | CC(=O)SC[C@H]1CCCCCC[C@H](C(N)=O)NC1=O>C(C)O>NC(=O)[C@H]1CCCCCC[C@H](CS)C(=O)N1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-37b24b9090dc4d9a9382a6652abf7b0e | CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)O)NC1=O.Nc1cccnc1>>CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)Nc2cccnc2)NC1=O | C(C)(=O)SC[C@@H]1C(N[C@H](CCCCCC1)C(=O)O)=O.NC=1C=NC=CC1.ON1N=NC2=C1C=CC=C2.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>>C(C)(=O)SC[C@@H]1C(N[C@H](CCCCCC1)C(=O)NC=1C=NC=CC1)=O | O[C:14]([C@H:13]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]([CH2:5][S:4][C:2]([CH3:1])=[O:3])[C:24](=[O:25])[NH:23]1)=[O:15].[NH2:16][c:17]1[cH:18][cH:19][cH:20][n:21][cH:22]1>>[CH3:1][C:2](=[O:3])[S:4][CH2:5][C@H:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([C:14](=[O:15])[NH:16][c:17]2[cH:18][cH... | CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)O)NC1=O.Nc1cccnc1 | CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)Nc2cccnc2)NC1=O | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1CCCCCCC[C@H](C(=O)Nc2cccnc2)N1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]:[#7;a:12]:[c:13]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]:[#7;a:12]:[c:13])-[#7:5]-[C:6]=[O;D1;H0:7] | null | [] | 0 | CELSIUS | 8 | HOUR | Trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid (0.100 g, 0.35 mmol), 3-aminopyridine (0.036 g, 0.38 mmol), 1-hydroxybenzotriazole (0.047 g, 0.035 mmol), and 4-methylmorpholine (0.077 mL, 0.70 mmol) are dissolved in methylene chloride (2.5 mL), and the reaction is cooled to 0° C. To this solution i... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CCCCNCCCC1.c1ccncc1 | HO- | C(Cl)Cl | 0 | 8 | CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)O)NC1=O.Nc1cccnc1>C(Cl)Cl>CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)Nc2cccnc2)NC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-039d993767fd48bca5979ee161469481 | CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)Nc2cccnc2)NC1=O>>O=C1N[C@@H](C(=O)Nc2cccnc2)CCCCCC[C@@H]1CS | C(C)(=O)SC[C@@H]1C(N[C@H](CCCCCC1)C(=O)NC=1C=NC=CC1)=O.Cl>>Cl.SC[C@@H]1C(N[C@H](CCCCCC1)C(=O)NC=1C=NC=CC1)=O | CC(=O)[S:23][CH2:22][C@@H:21]1[C:3](=[O:2])[NH:4][C@@H:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][cH:12][n:13][cH:14]2)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1>>[O:2]=[C:3]1[NH:4][C@@H:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][cH:12][n:13][cH:14]2)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C@@H:21]1[CH2... | CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)Nc2cccnc2)NC1=O | O=C1N[C@@H](C(=O)Nc2cccnc2)CCCCCC[C@@H]1CS | null | null | C(C)O | Reduction | OtherReaction | 7702cd666d5d9a9f1bdea3600e3b84cc62dd11d3f2cea261702317a39db4e581 | 18d802456fe85193570fdb3a00b25c8956a03b5a0210f708f961e42c1669d76e | O=C1CCCCCCC[C@H](C(=O)Nc2cccnc2)N1 | C-C(=O)-[S;H0;D2;+0:1]-[C:2]-[C:3]-[C:4](=[O;D1;H0:5])-[#7:6]>>[#7:6]-[C:4](=[O;D1;H0:5])-[C:3]-[C:2]-[SH;D1;+0:1] | null | [] | null | null | 90 | MINUTE | 3-{N-[[trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecan-10-yl]-carbonyl]-amino}-pyridine (0.040 g, 0.11 mmol) is dissolved in ethanol (1.0 mL). An aqueous solution of nitrogen-degasded 1N sodium hydroxide (0.33 mL, 0.33 mmol) is added, and the reaction is stirred for 90 minutes. The reaction is quenched with 1N hydroch... | 10.6084/m9.figshare.5104873.v1 | null | Carbo-thioester | Aliphatic thiol | null | null | C1CCCCNCCCC1.c1ccncc1 | HO- | C(C)O | null | 1.5 | CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)Nc2cccnc2)NC1=O>C(C)O>O=C1N[C@@H](C(=O)Nc2cccnc2)CCCCCC[C@@H]1CS |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-78b42a7c2bd74f04a8c7a9f150514491 | CC(=O)OCCN.CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)O)NC1=O>>CC(=O)OCCNC(=O)[C@H]1CCCCCC[C@H](CSC(C)=O)C(=O)N1 | C(C)(=O)SC[C@@H]1C(N[C@H](CCCCCC1)C(=O)O)=O.Cl.C(C)(=O)OCCN.ON1N=NC2=C1C=CC=C2.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>>C(C)(=O)OCCNC(=O)[C@H]1CCCCCC[C@@H](C(N1)=O)CSC(C)=O | [CH3:1][C:2](=[O:3])[O:4][CH2:5][CH2:6][NH2:7].O[C:8](=[O:9])[C@H:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C@H:17]([CH2:18][S:19][C:20]([CH3:21])=[O:22])[C:23](=[O:24])[NH:25]1>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][CH2:6][NH:7][C:8](=[O:9])[C@H:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C@H:17]([CH2:1... | CC(=O)OCCN.CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)O)NC1=O | CC(=O)OCCNC(=O)[C@H]1CCCCCC[C@H](CSC(C)=O)C(=O)N1 | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1CCCCCCCCN1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[C:9]-[NH2;D1;+0:10]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[C:9]-[C:8])-[#7:5]-[C:6]=[O;D1;H0:7] | null | [] | 0 | CELSIUS | 8 | HOUR | Trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid (0.15 g, 0.52 mmol), 1-acetoxy-2-aminoethane hydrochloride (0.073 g, 0.52 mmol), 1-hydroxybenzotriazole (0.12 g, 0.52 mmol), and 4-methylmorpholine (0.17 mL, 1.56 mmol) are dissolved in methylene chloride (3.0 mL), and the reaction is cooled to 0° C. ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CCCCNCCCC1 | HO- | C(Cl)Cl | 0 | 8 | CC(=O)OCCN.CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)O)NC1=O>C(Cl)Cl>CC(=O)OCCNC(=O)[C@H]1CCCCCC[C@H](CSC(C)=O)C(=O)N1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ee7debe1bbd340b6a45aa36abc48f31c | BrCc1ccccc1.CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)O)NC1=O>>CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)OCc2ccccc2)NC1=O | C(C)(=O)SC[C@@H]1C(N[C@H](CCCCCC1)C(=O)O)=O.C(C1=CC=CC=C1)Br.C([O-])([O-])=O.[Cs+].[Cs+]>>C(C)(=O)SC[C@@H]1C(N[C@H](CCCCCC1)C(=O)OCC1=CC=CC=C1)=O | Br[CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1.[CH3:1][C:2](=[O:3])[S:4][CH2:5][C@H:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([C:14](=[O:15])[OH:16])[NH:24][C:25]1=[O:26]>>[CH3:1][C:2](=[O:3])[S:4][CH2:5][C@H:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([C:14](=[O:15])[O:16][CH2:17][c:... | BrCc1ccccc1.CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)O)NC1=O | CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)OCc2ccccc2)NC1=O | null | null | CN(C=O)C.O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | O=C1CCCCCCC[C@H](C(=O)OCc2ccccc2)N1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7:5]-[C:6]-[C:7](=[O;D1;H0:8])-[OH;D1;+0:9]>>[#7:5]-[C:6]-[C:7](=[O;D1;H0:8])-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 8 | HOUR | Trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid (0.15 g, 0.52 mmol) is dissolved in dimethylformamide (2.5 mL). Benzyl bromide (0.062 mL, 0.52 mmol) and cesium carbonate (0.085 g, 0.26 mmol) are added, and the reaction is stirred at room temperature overnight. The reaction is diluted with water, an... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | C1CCCCNCCCC1.c1ccccc1 | HBr | CN(C=O)C.O | null | 8 | BrCc1ccccc1.CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)O)NC1=O>CN(C=O)C.O>CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)OCc2ccccc2)NC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-dd7e11ffe6e943828cba55b069dff563 | CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)N2C(=O)OC[C@H]2Cc2ccccc2)NC1=O.[OH-]>>CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)O)NC1=O | C(C)(=O)SC[C@@H]1C(N[C@H](CCCCCC1)C(=O)N1C(OC[C@H]1CC1=CC=CC=C1)=O)=O.O.[OH-].[Li+]>>C(C)(=O)SC[C@@H]1C(N[C@H](CCCCCC1)C(=O)O)=O | O=C1OC[C@@H](Cc2ccccc2)N1[C:14]([C@H:13]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]([CH2:5][S:4][C:2]([CH3:1])=[O:3])[C:18](=[O:19])[NH:17]1)=[O:15].[OH-:16]>>[CH3:1][C:2](=[O:3])[S:4][CH2:5][C@H:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([C:14](=[O:15])[OH:16])[NH:17][C:18]1=[O:19] | CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)N2C(=O)OC[C@H]2Cc2ccccc2)NC1=O.[OH-] | CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)O)NC1=O | null | null | O.O1CCCC1 | Acylation | OtherReaction | 1600b14cd479cdb7d3a4405c4b04d21fc0e71f247fcc6d65cda537ac98ed7da2 | d7ed181e654e8ac131125bbdc5aee5dc90548ccf7549838daacff3be49378f55 | O=C1CCCCCCCCN1 | O=C1-O-C-[C@@H](-C-c2:c:c:c:c:c:2)-N-1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[OH-;D0:8]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[OH;D1;+0:8])-[#7:5]-[C:6]=[O;D1;H0:7] | null | [] | 0 | CELSIUS | 45 | MINUTE | The more polar major chiral isomer of N-[[trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecan-10-yl]-carbonyl]-(R)-4-benzyl-2-oxazolidinone (1.23 g, 2.75 mmol) is dissolved in tetrahydrofuran (45.0 mL) and water (15.0 mL), and the reaction is cooled to 0° C. Lithium hydroxide hydrate (0.116 g, 2.75 mmol) is added, and the... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Substituted dicarboximide | Carboxylic acid | C1COCN1.c1ccccc1 | null | C1CCCCNCCCC1 | HO- | O.O1CCCC1 | 0 | 0.75 | CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)N2C(=O)OC[C@H]2Cc2ccccc2)NC1=O.[OH-]>O.O1CCCC1>CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)O)NC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-cd1d5c5dc1cf4e4bb0fa6676330d839a | CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)O)NC1=O.CCOC(=O)[C@@H]1C[C@@H](O)CN1>>CCOC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@H]1CCCCCC[C@H](CSC(C)=O)C(=O)N1 | C(C)(=O)SC[C@@H]1C(N[C@H](CCCCCC1)C(=O)O)=O.ON1N=NC2=C1C=CC=C2.CN1CCOCC1.Cl.C(C)OC([C@H]1NC[C@@H](C1)O)=O.Cl.CN(C)CCCN=C=NCC>>C(C)OC([C@H]1N(C[C@@H](C1)O)C(=O)[C@H]1CCCCCC[C@@H](C(N1)=O)CSC(C)=O)=O | O[C:12](=[O:13])[C@H:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C@H:21]([CH2:22][S:23][C:24]([CH3:25])=[O:26])[C:27](=[O:28])[NH:29]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[C@@H:6]1[CH2:7][C@@H:8]([OH:9])[CH2:10][NH:11]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C@@H:6]1[CH2:7][C@@H:8]([OH:9])[CH2:10][N:11]1[C:12](=[O:13])... | CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)O)NC1=O.CCOC(=O)[C@@H]1C[C@@H](O)CN1 | CCOC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@H]1CCCCCC[C@H](CSC(C)=O)C(=O)N1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | a590d96426a2fbaed42913d9daf8a16471a16de4978200f1d35a30a10009ebe7 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C1CCCCCCC[C@H](C(=O)N2CCCC2)N1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[C:12]1-[C:13]-[C:14]-[C:15]-[NH;D2;+0:16]-1>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:16]1-[C:15]-[C:14]-[C:13]-[C:12]-1-[C:10](=[O;D1;H0:11])-[#8:9]-[C:8])-[#7:5]-[C:6]=[O;D1;H0:7] | null | [] | 0 | CELSIUS | 8 | HOUR | The enantiomer of trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid of Example 16(0.23 g, 0.80 mmol), 1-hydroxybenzotriazole (0.11 g, 0.80 mmol), 4-methylmorpholine (0.22 mL, 2.0 mmol), and L-hydroxyproline ethyl ester hydrochloride (0.16 g, 0.80 mmol) are dissolved in methylene chloride (5.0 mL), an... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.C1CCCCNCCCC1 | HO- | C(Cl)Cl | 0 | 8 | CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)O)NC1=O.CCOC(=O)[C@@H]1C[C@@H](O)CN1>C(Cl)Cl>CCOC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@H]1CCCCCC[C@H](CSC(C)=O)C(=O)N1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b0cbfac023104194ba68e11d16883fb1 | CC(C)(C)OC(=O)CC1CCCCCCC(CO)NC1=O.O=C(O)Cc1cccs1>>CC(=O)SCC1CCCCCCC(CC(=O)OC(C)(C)C)C(=O)N1 | C(C)(C)(C)OC(=O)CC1C(NC(CCCCCC1)CO)=O.C(C)N(CC)CC.S1C(=CC=C1)CC(=O)O.C(C)N(CC)CC.C1(=CC=C(C=C1)S(=O)(=O)[O-])C.FC1=[N+](C=CC=C1)C>>C(C)(=O)SCC1CCCCCCC(C(N1)=O)CC(=O)OC(C)(C)C | O[CH2:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([CH2:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[C:22](=[O:23])[NH:24]1.OC([CH2:1][c:2]1ccc[s:4]1)=[O:3]>>[CH3:1][C:2](=[O:3])[S:4][CH2:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([CH2:14][C:15](=[O:16])[O:17][C:18]([C... | CC(C)(C)OC(=O)CC1CCCCCCC(CO)NC1=O.O=C(O)Cc1cccs1 | CC(=O)SCC1CCCCCCC(CC(=O)OC(C)(C)C)C(=O)N1 | null | null | C1=CC=CC=C1.CC(=O)C | Protection | OtherReaction | 189263d4d19565b9c5c001a81e8abf2a60b1807919ec489920cd4293a1993653 | 7a83c40990eef465e85ff66652874583517e7c7b69d7750d5f2438fef535f94e | O=C1CCCCCCCCN1 | O-C(=[O;H0;D1;+0:1])-[CH2;D2;+0:2]-[c;H0;D3;+0:3]1:[s;H0;D2;+0:4]:c:c:c:1.O-[CH2;D2;+0:5]-[C:6](-[C:7])-[#7:8]-[C:9]=[O;D1;H0:10]>>[C:7]-[C:6](-[CH2;D2;+0:5]-[S;H0;D2;+0:4]-[C;H0;D3;+0:3](-[CH3;D1;+0:2])=[O;H0;D1;+0:1])-[#7:8]-[C:9]=[O;D1;H0:10] | null | [] | null | null | 90 | MINUTE | 3-t-Butoxycarbonylmethyl-10-hydroxymethyl-2-oxo-1-azacyclodecane (0.50 g, 1.67 mmol) is dissolved in acetone (5.0 mL) and benzene (5.0 mL). Triethylamine (0.26 mL, 1.9 mmol) is added, followed by 2-fluoro-1-methylpyridinium toluene-4-sulfonate (0.54 g, 1.9 mmol), and the reaction is stirred at room temperature for 90 m... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Carbo-thioester | c1ccsc1 | null | C1CCCCNCCCC1 | HO- | C1=CC=CC=C1.CC(=O)C | null | 1.5 | CC(C)(C)OC(=O)CC1CCCCCCC(CO)NC1=O.O=C(O)Cc1cccs1>C1=CC=CC=C1.CC(=O)C>CC(=O)SCC1CCCCCCC(CC(=O)OC(C)(C)C)C(=O)N1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9f6126e0435c45d1b9864f1d5abc955e | CCOC(=O)C1CCCCCCC(=O)C(=O)N1.COP(=O)(CC(=O)OC(C)(C)C)OC>>CCOC(=O)C1CCCCCCC(=CC(=O)OC(C)(C)C)C(=O)N1 | O=C1NC(CCCCCCC1=O)C(=O)OCC.COP(=O)(OC)CC(=O)OC(C)(C)C>>C(C)(C)(C)OC(=O)C=C1C(NC(CCCCCC1)C(=O)OCC)=O | O=[C:13]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[NH:24][C:22]1=[O:23].COP(=O)(OC)[CH2:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](=[CH:14][C:15](=[O:16])[O:17][C:18]([... | CCOC(=O)C1CCCCCCC(=O)C(=O)N1.COP(=O)(CC(=O)OC(C)(C)C)OC | CCOC(=O)C1CCCCCCC(=CC(=O)OC(C)(C)C)C(=O)N1 | null | null | C1(=CC=CC=C1)C.C1CCOC1 | C-C Coupling | Wittig with Phosphonium | 46e674202571f664c893c061280f1959b89d65a5bd2e0a27e97f4079bf0d5665 | 79a946b42eb7e7aee42e09efe41630192c1745e07085cd7f7f88cc7b599f9082 | [CH]=C1CCCCCCCNC1=O | C-O-P(=O)(-O-C)-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].O=[C;H0;D3;+0:9](-[C:10]-[C:11])-[C:12](=[O;D1;H0:13])-[#7:14]-[C:15]-[C:16](-[#8:17])=[O;D1;H0:18]>>[#8:17]-[C:16](=[O;D1;H0:18])-[C:15]-[#7:14]-[C:12](=[O;D1;H0:13])-[C;H0;D3;+0:9](=[CH;D2;+0:1]-[C:2](=[O;D1;H0:3])-... | null | [] | null | null | 25 | MINUTE | Potassium hexamethyldisilylamide (40.5 mL of a 0.58M solution in toluene, 23.5 mmol) is added to THF (60 mL), and then cooled to 0° C. t-Butyl dimethylphosphonoacetate (4.6 mL, 23.5 mmol) is added dropwise, and the reaction is warmed to room temperature and stirred for 25 minutes. Ethyl 2,3-di-oxo-1-azacyclodecane-10-c... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ester | C1CCCCNCCCC1 | C1CCCCNCCCC1 | C1CCCCNCCCC1 | HO- | C1(=CC=CC=C1)C.C1CCOC1 | null | 0.416667 | CCOC(=O)C1CCCCCCC(=O)C(=O)N1.COP(=O)(CC(=O)OC(C)(C)C)OC>C1(=CC=CC=C1)C.C1CCOC1>CCOC(=O)C1CCCCCCC(=CC(=O)OC(C)(C)C)C(=O)N1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-17a0cf59456c4baa92e9560f5124e23f | CCOC(=O)C1CCCCCCC(=CC(=O)OC(C)(C)C)C(=O)N1>>CCOC(=O)C1CCCCCCC(CC(=O)OC(C)(C)C)C(=O)N1 | C(C)(C)(C)OC(=O)C=C1C(NC(CCCCCC1)C(=O)OCC)=O>>C(C)(C)(C)OC(=O)CC1C(NC(CCCCCC1)C(=O)OCC)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](=[CH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[C:22](=[O:23])[NH:24]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([CH2:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([C... | CCOC(=O)C1CCCCCCC(=CC(=O)OC(C)(C)C)C(=O)N1 | CCOC(=O)C1CCCCCCC(CC(=O)OC(C)(C)C)C(=O)N1 | null | [Pd] | C(C)(=O)OCC | Reduction | Hydrogenation (double to single) | c528462945509c32a83b30347f7f4ef4d89ae59c56cc702e111e9c5086d00dff | 9a50abf8d2e4cd9195d7a0cadbe97483a261a81cf70b653cfddd5ecf76d383a6 | O=C1CCCCCCCCN1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7:5]-[C:6](=[O;D1;H0:7])-[C;H0;D3;+0:8](=[CH;D2;+0:9]-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[C;D1;H3:16])-[C:17]-[C:18]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7:5]-[C:6](=[O;D1;H0:7])-[CH;D3;+0:8](-[CH2;D2;+0:9]-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13](-[C;D1;H3:... | null | [] | null | null | 4.5 | HOUR | Ethyl 3-t-butoxycarbonylmethylidene-2-oxo-1-azacyclodecane-10-carboxylate (2.85 g, 8.4 mmol) is dissolved in ethyl acetate (75 mL). 10% Pd/C (2.0 g) is added, and the reaction is stirred under an atmosphere of hydrogen for 4.5 hours. The reaction is filtered through Celite, and the solvent is removed. The crude product... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | C1CCCCNCCCC1 | C1CCCCNCCCC1 | C1CCCCNCCCC1 | null | [Pd].C(C)(=O)OCC | null | 4.5 | CCOC(=O)C1CCCCCCC(=CC(=O)OC(C)(C)C)C(=O)N1>[Pd].C(C)(=O)OCC>CCOC(=O)C1CCCCCCC(CC(=O)OC(C)(C)C)C(=O)N1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-429516784f194c80be8e088df5ef86d4 | CCOC(=O)C1CCCCCCC(CC(=O)OC(C)(C)C)C(=O)N1>>CC(C)(C)OC(=O)CC1CCCCCCC(CO)NC1=O | C(C)(C)(C)OC(=O)CC1C(NC(CCCCCC1)C(=O)OCC)=O.[BH4-].[Na+].CO>>C(C)(C)(C)OC(=O)CC1C(NC(CCCCCC1)CO)=O | CCO[C:17]([CH:16]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH:9]([CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C:20](=[O:21])[NH:19]1)=[O:18]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:17][OH:18])[NH:19][C:20]1=[O:21] | CCOC(=O)C1CCCCCCC(CC(=O)OC(C)(C)C)C(=O)N1 | CC(C)(C)OC(=O)CC1CCCCCCC(CO)NC1=O | null | null | C(C)(C)(C)O | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | O=C1CCCCCCCCN1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7]>>[C:4]-[C:3](-[CH2;D2;+0:1]-[OH;D1;+0:2])-[#7:5]-[C:6]=[O;D1;H0:7] | null | [] | 55 | CELSIUS | 1 | HOUR | The major isomer of ethyl 3-t-butoxycarbonylmethyl-2-oxo-1-azacyclodecane-10-carboxylate (0.68 g, 2.0 mmol) is dissolved in t-butanol (10 mL). Sodium borohydride (0.23 g, 6.0 mmol) is added and the reaction is warmed to 55° C. Methanol (2.0 mL) is added over a twenty minute period, and the reaction is kept at 55° C. fo... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CCCCNCCCC1 | HO- | C(C)(C)(C)O | 55 | 1 | CCOC(=O)C1CCCCCCC(CC(=O)OC(C)(C)C)C(=O)N1>C(C)(C)(C)O>CC(C)(C)OC(=O)CC1CCCCCCC(CO)NC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3ff5ad5cf75d47f1b22289091515d997 | CC(C)(C)OC(=O)CC1CCCCCCC(CS)NC1=O>>O=C(O)CC1CCCCCCC(CS)NC1=O | SCC1CCCCCCC(C(N1)=O)CC(=O)OC(C)(C)C>>SCC1CCCCCCC(C(N1)=O)CC(=O)O | CC(C)(C)[O:3][C:2](=[O:1])[CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]([CH2:13][SH:14])[NH:15][C:16]1=[O:17]>>[O:1]=[C:2]([OH:3])[CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]([CH2:13][SH:14])[NH:15][C:16]1=[O:17] | CC(C)(C)OC(=O)CC1CCCCCCC(CS)NC1=O | O=C(O)CC1CCCCCCC(CS)NC1=O | null | null | C(Cl)Cl | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | O=C1CCCCCCCCN1 | C-C(-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 | 8 | HOUR | 10-Mercaptomethyl-3-t-butoxycarbonylmethyl-2-oxo-1-azacyclodecane (0.21 g, 0.69 mmol) is dissolved in methylene chloride (15 mL). Gaseous hydrogen chloride is bubbled through the solvent for 15 minutes, and then the reaction is sealed and stirred overnight. The solvent is evaporated the next day to give 10-mercaptometh... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | C1CCCCNCCCC1 | Other | C(Cl)Cl | null | 8 | CC(C)(C)OC(=O)CC1CCCCCCC(CS)NC1=O>C(Cl)Cl>O=C(O)CC1CCCCCCC(CS)NC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4ea35438c1a34afdb409c8baaa96ef06 | CCOC(=O)CC(CCCCCCCCCCC(CC(=O)OCC)C(=O)OCc1ccccc1)NC(=O)OC(C)(C)C>>CCOC(=O)CC(CCCCCCCCCCC(CC(=O)OCC)C(=O)O)NC(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)NC(CC(=O)OCC)CCCCCCCCCCC(CC(=O)OCC)C(=O)OCC1=CC=CC=C1>>C(C)(C)(C)OC(=O)NC(CC(=O)OCC)CCCCCCCCCCC(CC(=O)OCC)C(=O)O | c1ccc(C[O:27][C:25]([CH:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[NH:28][C:29](=[O:30])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35])[CH2:19][C:20](=[O:21])[O:22][CH2:23][CH3:24])=[O:26])cc1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]... | CCOC(=O)CC(CCCCCCCCCCC(CC(=O)OCC)C(=O)OCc1ccccc1)NC(=O)OC(C)(C)C | CCOC(=O)CC(CCCCCCCCCCC(CC(=O)OCC)C(=O)O)NC(=O)OC(C)(C)C | null | [Pd] | C(C)(=O)OCC | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | null | [C:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1>>[C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4] | null | [] | null | null | 2 | HOUR | Diethyl 2-t-butoxycarbonylamino-13-benzyloxycarbonyl-1,14-tetradecanedicarboxylate (5.0 g, 8.87 mmol) is dissolved in ethyl acetate (150.0 mL), and 10% Pd-C (2.6 g) is added. The reaction flask is put under an atmosphere of hydrogen and stirred for 2 hours. The product is then filtered through a pad of Celite, and the ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | null | Other | [Pd].C(C)(=O)OCC | null | 2 | CCOC(=O)CC(CCCCCCCCCCC(CC(=O)OCC)C(=O)OCc1ccccc1)NC(=O)OC(C)(C)C>[Pd].C(C)(=O)OCC>CCOC(=O)CC(CCCCCCCCCCC(CC(=O)OCC)C(=O)O)NC(=O)OC(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-856e1c74c5fa4bfaa718c434d3d2dcd8 | CCOC(=O)CC(CCCCCCCCCCC(CC(=O)OCC)C(=O)O)NC(=O)OC(C)(C)C.ClCCl>>CCOC(=O)CC(N)CCCCCCCCCCC(CC(=O)OCC)C(=O)O.Cl | C(C)(C)(C)OC(=O)NC(CC(=O)OCC)CCCCCCCCCCC(CC(=O)OCC)C(=O)O.C(Cl)Cl>>Cl.NC(CC(=O)OCC)CCCCCCCCCCC(CC(=O)OCC)C(=O)O | CC(C)(C)OC(=O)[NH:8][CH:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]([CH2:20][C:21](=[O:22])[O:23][CH2:24][CH3:25])[C:26](=[O:27])[OH:28].ClC[Cl:29]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([NH2:8])[CH2:9][CH2:10][CH2:11][CH2:12]... | CCOC(=O)CC(CCCCCCCCCCC(CC(=O)OCC)C(=O)O)NC(=O)OC(C)(C)C.ClCCl | CCOC(=O)CC(N)CCCCCCCCCCC(CC(=O)OCC)C(=O)O.Cl | null | null | null | Miscellaneous | OtherReaction | 20ca630092c9d0b186049ded8d4724cd41b8cec5a9770e37b4b0e3b10fb39ea3 | b777363b1194e165a6e8ffea7fe0d21d29ef4e8f6652e2bc49cad8e827d3c935 | null | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7].Cl-C-[Cl;H0;D1;+0:8]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:2](-[C:3])-[NH2;D1;+0:1].[ClH;D0;+0:8] | null | [] | null | null | 2.5 | HOUR | Diethyl 2-t-butoxycarbonylamino-13-carboxy-1,14-tetradecanedicarboxylate (3.98 g, 8.40 mmol) is dissolved in methylene chloride (150.0 mL), and hydrogen chloride gas is bubbled through the solution for 15 minutes. The sealed reaction is stirred for 2.5 hours, and then the solvent is evaporated to give diethyl 2-amino-1... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carbamic ester.Ether.Boc | Primary amine | null | null | null | HCl | null | null | 2.5 | CCOC(=O)CC(CCCCCCCCCCC(CC(=O)OCC)C(=O)O)NC(=O)OC(C)(C)C.ClCCl>>CCOC(=O)CC(N)CCCCCCCCCCC(CC(=O)OCC)C(=O)O.Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-951c6a1597cb49a28e3182feddd4d406 | CCOC(=O)C1CCCCCCCCCCC(C(=O)OCC)C(=O)N1>>O=C(O)C1CCCCCCCCCCC(C(=O)O)C(=O)N1 | Cl.O=C1NC(CCCCCCCCCCC1C(=O)OCC)C(=O)OCC.[OH-].[Na+]>>O=C1NC(CCCCCCCCCCC1C(=O)O)C(=O)O | CC[O:3][C:2](=[O:1])[CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([C:16](=[O:17])[O:18]CC)[C:19](=[O:20])[NH:21]1>>[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([C:16](=[O:17])[OH:18])[C:19](=[O:20])[NH:21]1 | CCOC(=O)C1CCCCCCCCCCC(C(=O)OCC)C(=O)N1 | O=C(O)C1CCCCCCCCCCC(C(=O)O)C(=O)N1 | null | null | C(C)O | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | O=C1CCCCCCCCCCCCN1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5](=[O;D1;H0:6])-[#7:7]-[C:8]-[C:9](=[O;D1;H0:10])-[O;H0;D2;+0:11]-C-C>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[C:4]-[C:5](=[O;D1;H0:6])-[#7:7]-[C:8]-[C:9](=[O;D1;H0:10])-[OH;D1;+0:11] | null | [] | null | null | 3 | HOUR | Diethyl 2-oxo-1-azacyclotetradecane-3,14-dicarboxylate (1.14 g, 3.2 mmol; mixture of both diastereomers) is dissolved in ethanol (32.0 mL). Sodium hydroxide (9.6 mL of a 1N aqueous solution, 9.6 mmol) is added dropwise, and the solution is stirred at room temperature for 3 hours. The reaction is then acidified to pH 3 ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | C1CCCCCCNCCCCCC1 | Other | C(C)O | null | 3 | CCOC(=O)C1CCCCCCCCCCC(C(=O)OCC)C(=O)N1>C(C)O>O=C(O)C1CCCCCCCCCCC(C(=O)O)C(=O)N1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d4e78d67f9574f95b9763ece1f167e82 | O=C(O)C1CCCCCCCCCCC(C(=O)O)C(=O)N1>>C=C1CCCCCCCCCCC(C(=O)O)NC1=O | Cl.N1CCCCC1.O=C1NC(CCCCCCCCCCC1C(=O)O)C(=O)O.C=O>>C=C1C(NC(CCCCCCCCCC1)C(=O)O)=O | O=[C:1](O)[CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([C:14](=[O:15])[OH:16])[C:18](=[O:19])[NH:17]1>>[CH2:1]=[C:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([C:14](=[O:15])[OH:16])[NH:17][C:18]1=[O:19] | O=C(O)C1CCCCCCCCCCC(C(=O)O)C(=O)N1 | C=C1CCCCCCCCCCC(C(=O)O)NC1=O | null | null | N1=CC=CC=C1 | Miscellaneous | OtherReaction | 606ce5b982dd54d5ddad914cad200a87e4e95b65ba2c1a08c497beef81ebff6f | 52fef7a0b69b8402c1bf3297cc4d8b52084cb5f5aab54ba262b4908f5ccbe01d | C=C1CCCCCCCCCCCNC1=O | O-[C;H0;D3;+0:1](=O)-[CH;D3;+0:2](-[C:3]-[C:4])-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[CH;D3;+0:8](-[C:9](=[O;D1;H0:10])-[O;D1;H1:11])-[C:12]-[C:13]>>[C:13]-[C:12]-[CH;D3;+0:8](-[C:9](=[O;D1;H0:10])-[O;D1;H1:11])-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[C;H0;D3;+0:2](=[CH2;D1;+0:1])-[C:3]-[C:4] | null | [] | 65 | CELSIUS | null | null | 2-oxo-1-azacyclotetradecane-3,14-dicarboxylic acid (0.868 g, 2.9 mmol) is dissolved in pyridine (15.0 mL). Piperidine (0.060 mL, 0.59 mmol) is added, followed by paraformaldehyde (0.133 g, 4.43 mmol), and the reaction is heated to 65° C. for 4 hours. The reaction is then cooled to 0° C., and concentrated hydrochloric a... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amide | Secondary amide.Vinyl | C1CCCCCCNCCCCCC1 | C1CCCCCCNCCCCCC1 | C1CCCCCCNCCCCCC1 | Other | N1=CC=CC=C1 | 65 | null | O=C(O)C1CCCCCCCCCCC(C(=O)O)C(=O)N1>N1=CC=CC=C1>C=C1CCCCCCCCCCC(C(=O)O)NC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f8fa4f864ba6411e93d231ab3c63d6ce | BrCCCCCCCBr.COC(=O)CC(=O)OC(C)(C)C>>COC(=O)C(CCCCCCCBr)C(=O)OC(C)(C)C | BrCCCCCCCBr.[H-].[Na+].C(CC(=O)OC)(=O)OC(C)(C)C>>BrCCCCCCCC(C(=O)OC(C)(C)C)C(=O)OC | Br[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][Br:13].[CH3:1][O:2][C:3](=[O:4])[CH2:5][C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][Br:13])[C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20] | BrCCCCCCCBr.COC(=O)CC(=O)OC(C)(C)C | COC(=O)C(CCCCCCCBr)C(=O)OC(C)(C)C | null | null | CN(C=O)C | C-C Coupling | OtherReaction | 8175b6573d6439ec7ccc45bf6b48843ab56b46dccfc6504384c4766d09f35cc7 | d1817e44576d3a158547867a56245217a593d4f828a6d6dfaa8ed11276894e44 | null | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[#8:8]-[C:9](=[O;D1;H0:10])-[CH2;D2;+0:11]-[C:12](=[O;D1;H0:13])-[#8:14]-[C;D1;H3:15]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[CH;D3;+0:11](-[C:9](=[O;D1;H0:10])-[#8:8]-[C:5](-[C;D1;H3:4])(-[C;D1;H3:6])-[C;D1;H3:7])-[C:12](=[O;D1;H0:13])-[#8:14]-[C;D1;H3:15] | null | [] | null | null | 3 | HOUR | Sodium hydride (3.04 g of a 50% oil dispersion, 127 mmol) is suspended in dimethylformamide (300 ml) and the suspension is cooled to 0° C. t-Butyl methyl malonate (20.08 g, 115 mmol) is added dropwise slowly and the reaction mixture is warmed to room temperature. 1,7-Dibromoheptane (29.75 g, 115 mmol) is added dropwise... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester | Ester.Ester | null | null | null | HBr | CN(C=O)C | null | 3 | BrCCCCCCCBr.COC(=O)CC(=O)OC(C)(C)C>CN(C=O)C>COC(=O)C(CCCCCCCBr)C(=O)OC(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2f96668fb4f34f4cb203add2e1dbf0d7 | COC(=O)C(CCCCCCCBr)C(=O)OC(C)(C)C.[I-]>>COC(=O)C(CCCCCCCI)C(=O)OC(C)(C)C | BrCCCCCCCC(C(=O)OC(C)(C)C)C(=O)OC.[I-].[Na+]>>ICCCCCCCC(C(=O)OC(C)(C)C)C(=O)OC | Br[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20].[I-:13]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][I:13])[C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20] | COC(=O)C(CCCCCCCBr)C(=O)OC(C)(C)C.[I-] | COC(=O)C(CCCCCCCI)C(=O)OC(C)(C)C | null | null | CC(=O)C | Functional Group Interconversion | OtherReaction | e944a2acb95a43a23818321f2ac2f96ba2f2b8d34f52c1cfd1e3802d2403177f | e2ca6f9fe1078a3836d617896a4e5cc310fb155ca459b021e2b549b3e61f1df7 | null | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[I-;H0;D0:4]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[I;H0;D1;+0:4] | null | [] | null | null | null | null | t-Butyl methyl 7-bromoheptylmalonate (8.81 g, 25.1 mmol) is dissolved in acetone (50 ml). Sodium iodide (3.7 g, 25.1 mmol) is added and the mixture is stirred at reflux for 2 hours. The reaction mixture is filtered and the filtrate is concentrated to dryness. The residue is dissolved in methylene chloride and filtered ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Primary halide | null | null | null | Br- | CC(=O)C | null | null | COC(=O)C(CCCCCCCBr)C(=O)OC(C)(C)C.[I-]>CC(=O)C>COC(=O)C(CCCCCCCI)C(=O)OC(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-13270cd53a13413d86e4aa414a30ff1f | COC(=O)CC(CCCCCCCSC[C@H](N)CC(=O)OC)C(=O)OC(C)(C)C.ClCCl>>COC(=O)CC(CCCCCCCSC[C@H](N)CC(=O)OC)C(=O)O.Cl | N[C@H](CC(=O)OC)CSCCCCCCCC(CC(=O)OC)C(=O)OC(C)(C)C.C(Cl)Cl>>Cl.N[C@H](CC(=O)OC)CSCCCCCCCC(CC(=O)OC)C(=O)O | CC(C)(C)[O:25][C:23]([CH:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][S:14][CH2:15][C@H:16]([NH2:17])[CH2:18][C:19](=[O:20])[O:21][CH3:22])=[O:24].ClC[Cl:26]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][S:14][CH2:15][C@H:16]([... | COC(=O)CC(CCCCCCCSC[C@H](N)CC(=O)OC)C(=O)OC(C)(C)C.ClCCl | COC(=O)CC(CCCCCCCSC[C@H](N)CC(=O)OC)C(=O)O.Cl | null | null | null | Miscellaneous | OtherReaction | 1bdde8ea72e11cfbcc043bc42d0b84bb99dcaa21c1178d188748f396a79f95e1 | 24c87f8d54dd79ab3c2ede7dc82b7333299b3ef9471862dc0277670fba8260f4 | null | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].Cl-C-[Cl;H0;D1;+0:5]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[ClH;D0;+0:5] | null | [] | null | null | 2 | HOUR | Dimethyl (2R)-2-amino-12-t-butoxycarbonyl-4-thia-1,13-tridecanedicarboxylate (3.39 g, 8.36 mmol) is dissolved in methylene chloride (50 ml) and hydrogen chloride gas is bubbled through the solution for 5 minutes. The reaction mixture is stirred for 2 hours at room temperature. The solvent is evaporated to give dimethyl... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Ester.Boc | Carboxylic acid | null | null | null | HCl | null | null | 2 | COC(=O)CC(CCCCCCCSC[C@H](N)CC(=O)OC)C(=O)OC(C)(C)C.ClCCl>>COC(=O)CC(CCCCCCCSC[C@H](N)CC(=O)OC)C(=O)O.Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d95927d178064a35970f180e99ed80b8 | COC(=O)C1CCCCCCCSC[C@@H](C(=O)OC)NC1=O>>O=C(O)C1CCCCCCCSC[C@@H](C(=O)O)NC1=O | COC(=O)C1C(N[C@@H](CSCCCCCCC1)C(=O)OC)=O.[OH-].[Na+]>>C(=O)(O)C1C(N[C@@H](CSCCCCCCC1)C(=O)O)=O | C[O:3][C:2](=[O:1])[CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][S:12][CH2:13][C@@H:14]([C:15](=[O:16])[O:17]C)[NH:18][C:19]1=[O:20]>>[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][S:12][CH2:13][C@@H:14]([C:15](=[O:16])[OH:17])[NH:18][C:19]1=[O:20] | COC(=O)C1CCCCCCCSC[C@@H](C(=O)OC)NC1=O | O=C(O)C1CCCCCCCSC[C@@H](C(=O)O)NC1=O | null | null | CO | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | O=C1CCCCCCCCSCCN1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C:9](=[O;D1;H0:10])-[O;H0;D2;+0:11]-C>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[C:4]-[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C:9](=[O;D1;H0:10])-[OH;D1;+0:11] | null | [] | null | null | 4 | HOUR | Methyl (3R)-6-methoxycarbonyl-5oxo-1-thia-4-azacyclotridecane-3-carboxylate (2.39 g, 7.21 mmol) is suspended in methanol (75 ml) and 1N sodium hydroxide (22.0 ml, 22.0 mmol) is added. The mixture is stirred for 4 hours at room temperature. The solvent is evaporated and the residue is dissolved in water (150 ml). The aq... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | C1CCCCNCCSCCCC1 | Other | CO | null | 4 | COC(=O)C1CCCCCCCSC[C@@H](C(=O)OC)NC1=O>CO>O=C(O)C1CCCCCCCSC[C@@H](C(=O)O)NC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-65e3bf11fde04d758153eba4550a656c | O=C(O)C1CCCCCCCSC[C@@H](C(=O)O)NC1=O>>C=C1CCCCCCCSC[C@@H](C(=O)O)NC1=O | Cl.N1CCCCC1.C(=O)(O)C1C(N[C@@H](CSCCCCCCC1)C(=O)O)=O.C=O>>C=C1C(N[C@@H](CSCCCCCCC1)C(=O)O)=O | O=[C:1](O)[CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][S:10][CH2:11][C@@H:12]([C:13](=[O:14])[OH:15])[NH:16][C:17]1=[O:18]>>[CH2:1]=[C:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][S:10][CH2:11][C@@H:12]([C:13](=[O:14])[OH:15])[NH:16][C:17]1=[O:18] | O=C(O)C1CCCCCCCSC[C@@H](C(=O)O)NC1=O | C=C1CCCCCCCSC[C@@H](C(=O)O)NC1=O | null | null | N1=CC=CC=C1 | Miscellaneous | OtherReaction | ff8c773c54c3749caf140ff97e4a140e15d8bb81dd68b71552c083576e448385 | f72397e2bf1ed63b336420ad8491805dec3139bd28093f1f8ae2a191ad5039cf | C=C1CCCCCCCSCCNC1=O | O-[C;H0;D3;+0:1](=O)-[CH;D3;+0:2](-[C:3]-[C:4])-[C:5](=[O;D1;H0:6])-[#7:7]-[C:8]-[C:9](=[O;D1;H0:10])-[O;D1;H1:11]>>[C:4]-[C:3]-[C;H0;D3;+0:2](=[CH2;D1;+0:1])-[C:5](=[O;D1;H0:6])-[#7:7]-[C:8]-[C:9](=[O;D1;H0:10])-[O;D1;H1:11] | null | [] | 65 | CELSIUS | 2 | HOUR | (3R)-6-Carboxy-5-oxo-1-thia-4-azacyclotridecane -3-carboxylic acid (1.71 g, 5.64 mmol) is dissolved in pyridine (20 ml) and piperidine (0.096 g, 1.13 mmol) is added followed by paraformaldehyde (0.25 g, 8.46 mmol). The mixture is heated to 65° C. and stirred for 2 hours. The mixture is cooled to room temperature, poure... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Vinyl | C1CCCCNCCSCCCC1 | C1CCCCNCCSCCCC1 | C1CCCCNCCSCCCC1 | Other | N1=CC=CC=C1 | 65 | 2 | O=C(O)C1CCCCCCCSC[C@@H](C(=O)O)NC1=O>N1=CC=CC=C1>C=C1CCCCCCCSC[C@@H](C(=O)O)NC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8a5922e693b148e3b13ed802c0393b83 | COC(=O)[C@@H]1CSCCCCCCCC(CSC(C)=O)C(=O)N1>>O=C1N[C@H](C(=O)O)CSCCCCCCCC1CS | C(C)(=O)SCC1C(N[C@@H](CSCCCCCCC1)C(=O)OC)=O.O.[OH-].[Li+].Cl>>SCC1C(N[C@@H](CSCCCCCCC1)C(=O)O)=O | CC(=O)[S:19][CH2:18][CH:17]1[C:2](=[O:1])[NH:3][C@H:4]([C:5](=[O:6])[O:7]C)[CH2:8][S:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1>>[O:1]=[C:2]1[NH:3][C@H:4]([C:5](=[O:6])[OH:7])[CH2:8][S:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]1[CH2:18][SH:19] | COC(=O)[C@@H]1CSCCCCCCCC(CSC(C)=O)C(=O)N1 | O=C1N[C@H](C(=O)O)CSCCCCCCCC1CS | null | null | null | Reduction | OtherReaction | 1bcd8cbb2f136b4bcba1690e9ba45c4e43c89ba76f0e22de82a7d3fe318c82a9 | 5654c46fe4cb226f88ec3c899c7f9be1825c357673ea686958f9ef4883ee1db3 | O=C1CCCCCCCCSCCN1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C:9]-[S;H0;D2;+0:10]-C(-C)=O>>[O;D1;H0:7]=[C:6](-[#7:5]-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1])-[C:8]-[C:9]-[SH;D1;+0:10] | null | [] | null | null | 3 | HOUR | Methyl (3R)-6-(acetylthiomethyl)-5-oxo-1-thia-4-azacyclotridecane-3-carboxylate (Isomer B) (0.16 g, 0.44 mmol) is partially dissolved in nitrogen degassed tetrahydrofuran (10 ml) and water (5 ml). Lithium hydroxide monohydrate (0.056 g, 1.33 mmol) is added and the mixture is stirred at room temperature for 3 hours. The... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Carbo-thioester | Carboxylic acid.Aliphatic thiol | null | null | C1CCCCNCCSCCCC1 | HO- | null | null | 3 | COC(=O)[C@@H]1CSCCCCCCCC(CSC(C)=O)C(=O)N1>>O=C1N[C@H](C(=O)O)CSCCCCCCCC1CS |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2e9b771a72464fd2a4cf50637c02194b | C=C1CCCCCCCSC[C@@H](C(=O)O)NC1=O.CCO>>C=C1CCCCCCCSC[C@@H](C(=O)OCC)NC1=O | C=C1C(N[C@@H](CSCCCCCCC1)C(=O)O)=O.C(C)O>>C=C1C(N[C@@H](CSCCCCCCC1)C(=O)OCC)=O | [CH2:1]=[C:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][S:10][CH2:11][C@@H:12]([C:13](=[O:14])[OH:15])[NH:18][C:19]1=[O:20].O[CH2:16][CH3:17]>>[CH2:1]=[C:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][S:10][CH2:11][C@@H:12]([C:13](=[O:14])[O:15][CH2:16][CH3:17])[NH:18][C:19]1=[O:20] | C=C1CCCCCCCSC[C@@H](C(=O)O)NC1=O.CCO | C=C1CCCCCCCSC[C@@H](C(=O)OCC)NC1=O | null | null | null | Heteroatom Alkylation and Arylation | Esterification of Carboxylic Acids | 3f9a9ace480b666da05fcfe5450d12b5c1ea5b0d435c195e1dd4bd20281604bb | dcbf04ec563ed0e9dfc79070490a028958024079a671c385858bb18cc8ec995a | C=C1CCCCCCCSCCNC1=O | O-[CH2;D2;+0:1]-[C;D1;H3:2].[#7:3]-[C:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7]>>[#7:3]-[C:4]-[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C;D1;H3:2] | null | [] | null | null | 8 | HOUR | (3R)-6-Methylidene-5-oxo-1-thia-4-azacyclotridecane-3-carboxylic acid (0.16 g), 0.62 mmol) is dissolved in ethanol (5 ml) and hydrogen chloride gas is bubbled through the solution for 5 minutes. The solution is stirred overnight at room temperature and the solvent is evaporated to give ethyl (3R)-6-methylidene-5-oxo-1-... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | C1CCCCNCCSCCCC1 | HO- | null | null | 8 | C=C1CCCCCCCSC[C@@H](C(=O)O)NC1=O.CCO>>C=C1CCCCCCCSC[C@@H](C(=O)OCC)NC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2c4718ae54194d608dd1f148f41104d9 | BrCc1ccccc1.CC(=O)SCC1CCCCCCCSC[C@@H](C(=O)O)NC1=O>>CC(=O)SCC1CCCCCCCSC[C@@H](C(=O)OCc2ccccc2)NC1=O | C(C)(=O)SCC1C(N[C@@H](CSCCCCCCC1)C(=O)O)=O.C([O-])([O-])=O.[Cs+].[Cs+].C(C1=CC=CC=C1)Br>>C(C)(=O)SCC1C(N[C@@H](CSCCCCCCC1)C(=O)OCC1=CC=CC=C1)=O | Br[CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1.[CH3:1][C:2](=[O:3])[S:4][CH2:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][S:14][CH2:15][C@@H:16]([C:17](=[O:18])[OH:19])[NH:27][C:28]1=[O:29]>>[CH3:1][C:2](=[O:3])[S:4][CH2:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][S:14][CH2:1... | BrCc1ccccc1.CC(=O)SCC1CCCCCCCSC[C@@H](C(=O)O)NC1=O | CC(=O)SCC1CCCCCCCSC[C@@H](C(=O)OCc2ccccc2)NC1=O | null | null | O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | O=C1CCCCCCCCSC[C@@H](C(=O)OCc2ccccc2)N1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7:5]-[C:6]-[C:7](=[O;D1;H0:8])-[OH;D1;+0:9]>>[#7:5]-[C:6]-[C:7](=[O;D1;H0:8])-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 8 | HOUR | (3R)-6-(Acetylthiomethyl)-5-oxo-1-thia-4-azacyclotridecane-3-carboxylic acid (0.62 g, 1.78 mmol) is dissolved in dimethylformide (8 ml) and cesium carbonate (0.64 g, 1.96 mmol) is added, followed by benzyl bromide (0.31 g, 1.78 mmol). The mixture is stirred overnight at room temperature, poured into water (300 ml) and ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | C1CCCCNCCSCCCC1.c1ccccc1 | HBr | O | null | 8 | BrCc1ccccc1.CC(=O)SCC1CCCCCCCSC[C@@H](C(=O)O)NC1=O>O>CC(=O)SCC1CCCCCCCSC[C@@H](C(=O)OCc2ccccc2)NC1=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f3916e44658846b1b722f56ff1174fcc | BrCc1ccccc1.CC(C)(C)C(=O)SCC1CCCCCCCSC[C@@H](C(=O)O)NC1=O>>CC(C)(C)C(=O)SCC1CCCCCCCSC[C@@H](C(=O)OCc2ccccc2)NC1=O | O.C([O-])([O-])=O.[Cs+].[Cs+].C(C(C)(C)C)(=O)SCC1C(N[C@@H](CSCCCCCCC1)C(=O)O)=O.C(C1=CC=CC=C1)Br>>C(C(C)(C)C)(=O)SCC1C(N[C@@H](CSCCCCCCC1)C(=O)OCC1=CC=CC=C1)=O | Br[CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1.[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[S:7][CH2:8][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][S:17][CH2:18][C@@H:19]([C:20](=[O:21])[OH:22])[NH:30][C:31]1=[O:32]>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[S:7][CH2:8][CH:9]1[CH2:10][CH2:11]... | BrCc1ccccc1.CC(C)(C)C(=O)SCC1CCCCCCCSC[C@@H](C(=O)O)NC1=O | CC(C)(C)C(=O)SCC1CCCCCCCSC[C@@H](C(=O)OCc2ccccc2)NC1=O | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | O=C1CCCCCCCCSC[C@@H](C(=O)OCc2ccccc2)N1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7:5]-[C:6]-[C:7](=[O;D1;H0:8])-[OH;D1;+0:9]>>[#7:5]-[C:6]-[C:7](=[O;D1;H0:8])-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 8 | HOUR | (3R)-6-(Pivaloylthiomethyl)-5-oxo-1-thia-4-azacyclotridecane-3-carboxylic acid (0.25 g, 0.64 mmol) is dissolved in dimethylformamide (5 ml) and cesium carbonate (0.23 g, 0.71 mmol) is added, followed by benzyl bromide (0.11 g, 0.64 mmol). The mixture is stirred overnight at room temperature, poured into water (300 ml) ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | C1CCCCNCCSCCCC1.c1ccccc1 | HBr | CN(C=O)C | null | 8 | BrCc1ccccc1.CC(C)(C)C(=O)SCC1CCCCCCCSC[C@@H](C(=O)O)NC1=O>CN(C=O)C>CC(C)(C)C(=O)SCC1CCCCCCCSC[C@@H](C(=O)OCc2ccccc2)NC1=O |
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