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-c3a75813d0b24864aa4f7cd526efd6aa | ord-ce3b51218d7a4b3ea8639ec7b67345cb | BrBr.CCc1ccc(O)cc1>>CCc1ccc(O)c(Br)c1 | BrBr.C(C)C1=CC=C(C=C1)O>>BrC1=C(C=CC(=C1)CC)O | Br[Br:9].[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:8][cH:10]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[c:8]([Br:9])[cH:10]1 | BrBr.CCc1ccc(O)cc1 | CCc1ccc(O)c(Br)c1 | null | null | C(Cl)(Cl)Cl.CO | Functional Group Interconversion | Bromination | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | Br-[Br;H0;D1;+0:1].[O;D1;H1:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:3](-[O;D1;H1:2]):[c:4] | null | [] | null | null | null | null | 8.41 ml of bromine in 100 ml of CHCl3 were added dropwise within 2 hrs. to a solution, cooled to 0° C., of 20 g of 4-ethylphenol in 200 ml of CHCI3 and 100 ml of MeOH. The reaction mixture was left to warm to room temperature and was concentrated. The product was isolated by extraction. There were obtained 33.14 g of 2... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | C(Cl)(Cl)Cl.CO | null | null | BrBr.CCc1ccc(O)cc1>C(Cl)(Cl)Cl.CO>CCc1ccc(O)c(Br)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dfc65f7070c340c88b7acea8fc4cc1db | CCOc1cc(O)cc(C(Nc2ccc(C#N)cc2)C(=O)OC)c1.Nc1cccc(B(O)O)c1>>CCOc1cc(-c2cccc(N)c2)cc(C(Nc2ccc(C#N)cc2)C(=O)OC)c1 | C(#N)C1=CC=C(C=C1)NC(C(=O)OC)C1=CC(=CC(=C1)O)OCC.NC=1C=C(C=CC1)B(O)O>>NC=1C=C(C=CC1)C1=CC(=CC(=C1)OCC)C(C(=O)OC)NC1=CC=C(C=C1)C#N | O[c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[cH:30][c:15]([CH:16]([NH:17][c:18]2[cH:19][cH:20][c:21]([C:22]#[N:23])[cH:24][cH:25]2)[C:26](=[O:27])[O:28][CH3:29])[cH:14]1.OB(O)[c:7]1[cH:8][cH:9][cH:10][c:11]([NH2:12])[cH:13]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11]([NH2:12])[cH:13]2)[cH:14][c:1... | CCOc1cc(O)cc(C(Nc2ccc(C#N)cc2)C(=O)OC)c1.Nc1cccc(B(O)O)c1 | CCOc1cc(-c2cccc(N)c2)cc(C(Nc2ccc(C#N)cc2)C(=O)OC)c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 8e82e1107322fd62a4062bcf4fa2d39a87808625d997a13c1762797b47376e7c | e0e65caf964d4adfc16a221f1dbdadbd1ecd905f70d03ff1de520ebd8aa47216 | c1ccc(NCc2cccc(-c3ccccc3)c2)cc1 | O-B(-O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | null | [] | null | null | null | null | Analogously to Example 155, from methyl (RS)-(4-cyano-phenylamino)-(3-ethoxy-5-hydroxy-phenyl)-acetate via methyl (RS)-(4-cyano-phenylamino)-(3-ethoxy-5-trifluoro-methanesulphonyloxy-phenyl)-acetate by reaction with 3-aminophenylboronic acid there was obtained the compound methyl (RS)-(3′-amino-5-ethoxy-biphenyl-3-yl)-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HO-.B | null | null | null | CCOc1cc(O)cc(C(Nc2ccc(C#N)cc2)C(=O)OC)c1.Nc1cccc(B(O)O)c1>>CCOc1cc(-c2cccc(N)c2)cc(C(Nc2ccc(C#N)cc2)C(=O)OC)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-748f4211b33d470e9039088b6de436fc | CCOc1cc(O)cc(C(Nc2ccc(C#N)cc2)C(=O)OC)c1.OB(O)c1cccs1>>CCOc1cc(-c2cccs2)cc(C(Nc2ccc(C#N)cc2)C(=O)OC)c1 | C(#N)C1=CC=C(C=C1)NC(C(=O)OC)C1=CC(=CC(=C1)O)OCC.S1C(=CC=C1)B(O)O>>C(#N)C1=CC=C(C=C1)NC(C(=O)OC)C1=CC(=CC(=C1)C=1SC=CC1)OCC | O[c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[cH:28][c:13]([CH:14]([NH:15][c:16]2[cH:17][cH:18][c:19]([C:20]#[N:21])[cH:22][cH:23]2)[C:24](=[O:25])[O:26][CH3:27])[cH:12]1.OB(O)[c:7]1[cH:8][cH:9][cH:10][s:11]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][s:11]2)[cH:12][c:13]([CH:14]([NH:15][c:16]2[cH:17][c... | CCOc1cc(O)cc(C(Nc2ccc(C#N)cc2)C(=O)OC)c1.OB(O)c1cccs1 | CCOc1cc(-c2cccs2)cc(C(Nc2ccc(C#N)cc2)C(=O)OC)c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 449a3f909d853734ccd5b58934fe8f3777c713f88474bc06c4a348dfe5f65c47 | e0e65caf964d4adfc16a221f1dbdadbd1ecd905f70d03ff1de520ebd8aa47216 | c1ccc(NCc2cccc(-c3cccs3)c2)cc1 | O-B(-O)-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1.O-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1):[c:9]:[c:10] | null | [] | null | null | null | null | Analogously to Example 145, from methyl (RS)-(4-cyano-phenylamino)-(3-ethoxy-5-hydroxy-phenyl)-acetate via methyl (RS)-(4-cyano-phenylamino)-(3-ethoxy-5-trifluoro-methanesulphonyloxy-phenyl)-acetate by reaction with thiophene-2-boronic acid there was obtained the compound methyl (RS)-(4-cyano-phenylamino)-(3-ethoxy-5-t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Boronic acid | null | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1.c1ccccc1 | HO-.B | null | null | null | CCOc1cc(O)cc(C(Nc2ccc(C#N)cc2)C(=O)OC)c1.OB(O)c1cccs1>>CCOc1cc(-c2cccs2)cc(C(Nc2ccc(C#N)cc2)C(=O)OC)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8f952eae2dd24641aa2939b666ca49f6 | C#C[Si](C)(C)C.CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(Br)cc(CO)c1>>CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(C#C[Si](C)(C)C)cc(CO)c1 | C[Si](C)(C)C#C.BrC=1C=C(C=C(C1)CO)C(C(=O)OCC)NC1=CC=C(C=C1)C#N.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)C#C[Si](C)(C)C)CO | [CH:19]#[C:20][Si:21]([CH3:22])([CH3:23])[CH3:24].Br[c:18]1[cH:17][c:16]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[NH:7][c:8]2[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]2)[cH:29][c:26]([CH2:27][OH:28])[cH:25]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]1)[c:1... | C#C[Si](C)(C)C.CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(Br)cc(CO)c1 | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(C#C[Si](C)(C)C)cc(CO)c1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | C(C)N(CC)CC | C-C Coupling | Sonogashira alkyne_aryl halide | 15c08902746c61a960c314898ce6bb5fcc5e189f9e057388c59dba9ec9d0c81c | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccc(CNc2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[#14:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C:10]#[CH;D1;+0:11]>>[C;D1;H3:6]-[#14:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C:10]#[C;H0;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | 30 | MINUTE | 403 mg of the ethyl (RS)-(3-bromo-5-hydroxymethyl-phenyl)-(4-cyano-phenylamino)-acetate described in Example 156.2 were suspended in 3.1 ml of triethylamine and 4 mg of triphenylphosphine were added. Argon was conducted through the reaction mixture for 30 min. Then, 7 mg of palladium(II) acetate and 0.22 ml of trimethy... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HBr | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(C)N(CC)CC | null | 0.5 | C#C[Si](C)(C)C.CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(Br)cc(CO)c1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(C)N(CC)CC>CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(C#C[Si](C)(C)C)cc(CO)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ca099d0d7c624a328aad0b0607c66f7b | C1CCNC1.CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(C#C[Si](C)(C)C)cc(CO)c1>>CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(C#C[Si](C)(C)C)cc(CN2CCCC2)c1 | N1CCCC1.C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)C#C[Si](C)(C)C)CO.CS(=O)(=O)Cl>>C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)C#C[Si](C)(C)C)CN1CCCC1 | [NH:28]1[CH2:29][CH2:30][CH2:31][CH2:32]1.O[CH2:27][c:26]1[cH:25][c:18]([C:19]#[C:20][Si:21]([CH3:22])([CH3:23])[CH3:24])[cH:17][c:16]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[NH:7][c:8]2[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]2)[cH:33]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][c:8]1[cH:9][cH:10][c:11]([C... | C1CCNC1.CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(C#C[Si](C)(C)C)cc(CO)c1 | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(C#C[Si](C)(C)C)cc(CN2CCCC2)c1 | null | null | C(C)N(CC)CC.C(Cl)Cl.C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 5b5461e2c999b5ff4ebd02389aabcfa6da1d5461f5b1011870f0b8680e19702d | 87693a475e46c41583976158ec46dcaf8be8cc05c5635654a6a68033770f8d5c | c1ccc(NCc2cccc(CN3CCCC3)c2)cc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]1-[C:6]-[C:7]-[C:8]-[NH;D2;+0:9]-1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:9]1-[C:5]-[C:6]-[C:7]-[C:8]-1):[c:4] | null | [] | null | null | 8 | HOUR | 398 mg of the ethyl (RS)-(4-cyano-phenylamino)-(3-hydroxymethyl-5-trimethylsilanylethynyl-phenyl)-acetate described in Example 156.3 were dissolved in 6 ml of CH2Cl2 g and 0.41 ml of triethylamine followed by 0.1 ml of methanesulphonyl chloride were added dropwise at 0° C. The mixture was stirred overnight and an inter... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.c1ccccc1.C1CC[NH]C1 | HO- | C(C)N(CC)CC.C(Cl)Cl.C1CCOC1 | null | 8 | C1CCNC1.CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(C#C[Si](C)(C)C)cc(CO)c1>C(C)N(CC)CC.C(Cl)Cl.C1CCOC1>CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(C#C[Si](C)(C)C)cc(CN2CCCC2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-01242c882cb54270b05c4b9d92937076 | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(C#C[Si](C)(C)C)cc(CN2CCCC2)c1>>C#Cc1cc(CN2CCCC2)cc(C(Nc2ccc(C#N)cc2)C(=O)OCC)c1 | O.C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)C#C[Si](C)(C)C)CN1CCCC1.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)CN1CCCC1)C#C | C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][c:5]([CH2:6][N:7]2[CH2:8][CH2:9][CH2:10][CH2:11]2)[cH:12][c:13]([CH:14]([NH:15][c:16]2[cH:17][cH:18][c:19]([C:20]#[N:21])[cH:22][cH:23]2)[C:24](=[O:25])[O:26][CH2:27][CH3:28])[cH:29]1>>[CH:1]#[C:2][c:3]1[cH:4][c:5]([CH2:6][N:7]2[CH2:8][CH2:9][CH2:10][CH2:11]2)[cH:12][c:13]([CH:14]([NH... | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(C#C[Si](C)(C)C)cc(CN2CCCC2)c1 | C#Cc1cc(CN2CCCC2)cc(C(Nc2ccc(C#N)cc2)C(=O)OCC)c1 | null | null | C1CCOC1 | Deprotection | TMS deprotection from alkyne | e85676bb81da384790c9c858d44f182cdd01e3a79f77f7a239fe38487234cb96 | 56d526d7c9cb1bd7bee4940e216a9b1dd4597fd025a186b8d6e4675d8f4db26b | c1ccc(NCc2cccc(CN3CCCC3)c2)cc1 | C-[Si](-C)(-C)-[C;H0;D2;+0:1]#[C:2]-[c:3]>>[CH;D1;+0:1]#[C:2]-[c:3] | 24.6 | [{"value": 24.6, "product": "C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)CN1CCCC1)C#C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | 130 mg of the ethyl (RS)-(4-cyano-phenylamino)-(3-pyrrolidin-1-ylmethyl-5-trimethylsilanylethynyl-phenyl)-acetate described in Example 156.4 were dissolved in 2 ml of THF and treated at 0° C. with 0.43 ml of a 1 molar solution of tetrabutylammonium fluoride in THF. After 5 hrs. at 0° C. water was added to the reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne.Silyl protective group | Alkyne | null | null | c1ccccc1.C1CC[NH]C1.c1ccccc1 | Other | C1CCOC1 | null | 5 | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(C#C[Si](C)(C)C)cc(CN2CCCC2)c1>C1CCOC1>C#Cc1cc(CN2CCCC2)cc(C(Nc2ccc(C#N)cc2)C(=O)OCC)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-95c7c21a21b646cd96c5166a49adad2b | CC(C)(CO)CO.COc1cc(Br)c(C=O)cc1OC>>COc1cc(Br)c(C2OCC(C)(C)CO2)cc1OC | BrC1=C(C=O)C=C(C(=C1)OC)OC.CC(CO)(CO)C.C1(=CC=C(C=C1)S(=O)(=O)O)C>>BrC1=C(C=C(C(=C1)OC)OC)C1OCC(CO1)(C)C | O[CH2:10][C:11]([CH3:12])([CH3:13])[CH2:14][OH:15].[CH3:1][O:2][c:3]1[cH:4][c:5]([Br:6])[c:7]([CH:8]=[O:9])[cH:16][c:17]1[O:18][CH3:19]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([Br:6])[c:7]([CH:8]2[O:9][CH2:10][C:11]([CH3:12])([CH3:13])[CH2:14][O:15]2)[cH:16][c:17]1[O:18][CH3:19] | CC(C)(CO)CO.COc1cc(Br)c(C=O)cc1OC | COc1cc(Br)c(C2OCC(C)(C)CO2)cc1OC | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 09991f411aacffcc904d1b314d4846ed4bc3fcd70ecd0a878cedf349d9162730 | 7ac65b5a5f576337ce8e86e0130eb9b4757ca21b2419a0e82bbdfd5def30ee73 | c1ccc(C2OCCCO2)cc1 | O-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C:5]-[OH;D1;+0:6].[O;H0;D1;+0:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:3]-[C:2]1(-[C;D1;H3:4])-[C:5]-[O;H0;D2;+0:6]-[CH;D3;+0:8](-[c:9](:[c:10]):[c:11])-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-1 | 104.8 | [{"value": 104.8, "product": "BrC1=C(C=C(C(=C1)OC)OC)C1OCC(CO1)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3.6 g of 2-bromo-4,5-dimethoxybenzaldehyde and 3.22 g of 2,2-dimethyl-1,3-propanediol were dissolved in 200 ml of toluene and boiled at reflux in the presence of 0.8 g of p-toluenesulphonic acid for 3 hrs. Then, the reaction mixture was left to cool to room temperature and was washed with NaHCO3 solution, water and sat... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary alcohol.Primary alcohol | Ether.Ether | null | C1COCOC1 | c1ccccc1.C1COCOC1 | HO- | C1(=CC=CC=C1)C | null | null | CC(C)(CO)CO.COc1cc(Br)c(C=O)cc1OC>C1(=CC=CC=C1)C>COc1cc(Br)c(C2OCC(C)(C)CO2)cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4e312c7d5cef478daadc0b3f0424a9fc | CC(=O)OC(C)=O.[H]/N=C(\NO)c1cc(OC)c(OC)cc1C1OCC(C)(C)CO1>>COc1cc(-c2noc(C)n2)c(C2OCC(C)(C)CO2)cc1OC | CC1(COC(OC1)C1=C(/C(=N/[H])/NO)C=C(C(=C1)OC)OC)C.C1CCC2=NCCCN2CC1.C(C)(=O)OC(C)=O>>CC1(COC(OC1)C1=C(C=C(C(=C1)OC)OC)C1=NOC(=N1)C)C | CC(=O)O[C:9](=O)[CH3:10].[H]/[N:11]=[C:6](/[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:22]([O:23][CH3:24])[cH:21][c:12]1[CH:13]1[O:14][CH2:15][C:16]([CH3:17])([CH3:18])[CH2:19][O:20]1)[NH:7][OH:8]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][o:8][c:9]([CH3:10])[n:11]2)[c:12]([CH:13]2[O:14][CH2:15][C:16]([CH3:17])([CH3:18])[CH2:19... | CC(=O)OC(C)=O.[H]/N=C(\NO)c1cc(OC)c(OC)cc1C1OCC(C)(C)CO1 | COc1cc(-c2noc(C)n2)c(C2OCC(C)(C)CO2)cc1OC | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 83d74419ff23822a71a72198e1add1da14c578c3a3aedd8c2d7641eb708a2ed0 | f5e2612cf363c86441510a6512f4e0e218eb5eb4b9bc4bc3067da236e5bd3085 | c1ccc(C2OCCCO2)c(-c2ncon2)c1 | C-C(=O)-O-[C;H0;D3;+0:1](=O)-[C;D1;H3:2].[#8:3]-[C:4](-[c:5](:[c:6]):[c;H0;D3;+0:7](/[C;H0;D3;+0:8](=[N;H0;D2;+0:9]/[H])-[NH;D2;+0:10]-[OH;D1;+0:11]):[c:12]:[c:13])-[#8:14]>>[#8:3]-[C:4](-[c:5](:[c:6]):[c;H0;D3;+0:7](-[c;H0;D3;+0:8]1:[n;H0;D2;+0:9]:[c;H0;D3;+0:1](-[C;D1;H3:2]):[o;H0;D2;+0:11]:[n;H0;D2;+0:10]:1):[c:12]:... | null | [] | null | null | 1 | HOUR | A mixture of 1.34 g of (E)- and/or (Z)-2-(5,5-dimethyl-[1,3]dioxan-2-yl)-N-hydroxy-4,5-dimethoxy-benzamidine, 1.20 ml of DBU and 0.61 ml of acetic anhydride in 50 ml of DMF was stirred for 1 hr. at room temperature and subsequently for 2 hrs. at 80° C. Subsequently, the DMF was removed in a vacuum and the residue was t... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.C1COCOC1 | HO- | CN(C)C=O | null | 1 | CC(=O)OC(C)=O.[H]/N=C(\NO)c1cc(OC)c(OC)cc1C1OCC(C)(C)CO1>CN(C)C=O>COc1cc(-c2noc(C)n2)c(C2OCC(C)(C)CO2)cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3892e0a5d0954b078cc4ca89364d53b1 | COc1cc(-c2noc(C)n2)c(C2OCC(C)(C)CO2)cc1OC>>COc1cc(C=O)c(-c2noc(C)n2)cc1OC | C(=O)(O)[O-].[Na+].CC1(COC(OC1)C1=C(C=C(C(=C1)OC)OC)C1=NOC(=N1)C)C.Cl>>COC1=CC(=C(C=O)C=C1OC)C1=NOC(=N1)C | CC1(C)CO[CH:6]([c:8]2[c:5](-[c:9]3[n:10][o:11][c:12]([CH3:13])[n:14]3)[cH:4][c:3]([O:2][CH3:1])[c:16]([O:17][CH3:18])[cH:15]2)[O:7]C1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[c:8](-[c:9]2[n:10][o:11][c:12]([CH3:13])[n:14]2)[cH:15][c:16]1[O:17][CH3:18] | COc1cc(-c2noc(C)n2)c(C2OCC(C)(C)CO2)cc1OC | COc1cc(C=O)c(-c2noc(C)n2)cc1OC | null | null | CC(=O)C | Miscellaneous | Acetal hydrolysis to aldehyde | 9643cd1f284304118e26aebdc76b0b03ee6faac15f6438b853cf9a59ad303209 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | c1ccc(-c2ncon2)cc1 | C-C1(-C)-C-O-[CH;D3;+0:1](-[c;H0;D3;+0:2]2:[c:3]:[c:4]:[c:5]:[c:6]:[c;H0;D3;+0:7]:2-[c;H0;D3;+0:8]2:[#7;a:9]:[#8;a:10]:[c:11](-[C;D1;H3:12]):[#7;a:13]:2)-[O;H0;D2;+0:14]-C-1>>[C;D1;H3:12]-[c:11]1:[#7;a:13]:[c;H0;D3;+0:8](-[c;H0;D3;+0:2]2:[c:3]:[c:4]:[c:5]:[c:6]:[c;H0;D3;+0:7]:2-[CH;D2;+0:1]=[O;H0;D1;+0:14]):[#7;a:9]:[#... | null | [] | null | null | null | null | g of 3-[2-(5,5-dimethyl-[1,3]dioxan-2-yl)-4,5-dimethoxy-phenyl]-5-methyl-[1,2,4]-oxadiazole were stirred in 100 ml of acetone in the presence of 10 ml of concentrated HCl for 3 hrs. at room temperature. Then, the pH of the reaction mixture was adjusted to 7 with saturated NaHCO3 solution, the acetone was removed in a v... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | C1COCOC1.c1ncon1.c1ccccc1 | c1ccccc1.c1ncon1 | c1ccccc1.c1ncon1 | HO- | CC(=O)C | null | null | COc1cc(-c2noc(C)n2)c(C2OCC(C)(C)CO2)cc1OC>CC(=O)C>COc1cc(C=O)c(-c2noc(C)n2)cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0d2a57f66e734e69843a47f74f457a02 | CCOC(=O)C(Nc1ccc(C#N)cc1)c1ccc(OC)c(SC)c1>>CCOC(=O)C(Nc1ccc(C#N)cc1)c1ccc(O)c(SC)c1 | B(Br)(Br)Br.C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=C(C=C1)OC)SC>>C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=C(C=C1)O)SC | C[O:20][c:19]1[cH:18][cH:17][c:16]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[NH:7][c:8]2[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]2)[cH:24][c:21]1[S:22][CH3:23]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]1)[c:16]1[cH:17][cH:18][c:19]([OH:20])[c:21]([S:22][CH... | CCOC(=O)C(Nc1ccc(C#N)cc1)c1ccc(OC)c(SC)c1 | CCOC(=O)C(Nc1ccc(C#N)cc1)c1ccc(O)c(SC)c1 | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(CNc2ccccc2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 64 | [{"value": 64.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | A 1M solution of BBr3 in CH2Cl2 (4.5 ml, 4.5 mmol) was added at −78° C. to a solution of the ethyl (RS)-(4-cyano-phenylamino)-(4-methoxy-3-methylsulphanyl-phenyl)-acetate (320 mg, 0.899 mmol) obtained in Example 167.2 in CH2Cl2 (10 ml). The mixture was stirred at −78° C. for 5 min., at 0° C. for 30 min. and at room tem... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccccc1 | Other | C(Cl)Cl | 0 | 2 | CCOC(=O)C(Nc1ccc(C#N)cc1)c1ccc(OC)c(SC)c1>C(Cl)Cl>CCOC(=O)C(Nc1ccc(C#N)cc1)c1ccc(O)c(SC)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4dcf6d507e144db5bc4676cb76c08169 | CC(C)I.CCOC(=O)C(Nc1ccc(C#N)cc1)c1ccc(O)c(SC)c1>>CCOC(=O)C(Nc1ccc(C#N)cc1)c1ccc(OC(C)C)c(SC)c1 | O.C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=C(C=C1)O)SC.C(=O)([O-])[O-].[Cs+].[Cs+].C(C)(C)I>>C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=C(C=C1)OC(C)C)SC | I[CH:21]([CH3:22])[CH3:23].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]1)[c:16]1[cH:17][cH:18][c:19]([OH:20])[c:24]([S:25][CH3:26])[cH:27]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]1)[c:16]1[cH:17][cH:18][c... | CC(C)I.CCOC(=O)C(Nc1ccc(C#N)cc1)c1ccc(O)c(SC)c1 | CCOC(=O)C(Nc1ccc(C#N)cc1)c1ccc(OC(C)C)c(SC)c1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | bff4876be49b448135c783dd3eeeb68ab3cc5bdc91beadda8a9095106cd5c747 | cf768afb66ed5041aefdce1fa6d1e40995a1ab7c4b4a4ca47544fe49ee1e629f | c1ccc(CNc2ccccc2)cc1 | I-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[CH;D3;+0:1](-[C;D1;H3:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 63 | [{"value": 63.0, "product": "C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=C(C=C1)OC(C)C)SC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.8, "product": "C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=C(C=C1)OC(C)C)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of the ethyl (RS)-(4-cyano-phenylamino)-(4-hydroxy-3-methylsulphanyl-phenyl)-acetate (198 mg, 0.58 mmol) described in Example 168.1, Cs2CO3 (227 mg, 0.64 mmol) and isopropyl iodide (58 μl, 0.58 mmol) in acetone (3 ml) was heated under reflux for 4 h. Water was added and the mixture was extracted with CH2Cl... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HI | CC(=O)C | null | null | CC(C)I.CCOC(=O)C(Nc1ccc(C#N)cc1)c1ccc(O)c(SC)c1>CC(=O)C>CCOC(=O)C(Nc1ccc(C#N)cc1)c1ccc(OC(C)C)c(SC)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a350d40117d1481bb553c6a2595b1590 | CCc1cc(Br)ccc1OC.CN(C)C=O>>CCc1cc(C=O)ccc1OC | [Li]CCCC.CCCCCC.CN(C)C=O.BrC1=CC(=C(C=C1)OC)CC>>C(C)C=1C=C(C=O)C=CC1OC | Br[c:5]1[cH:4][c:3]([CH2:2][CH3:1])[c:10]([O:11][CH3:12])[cH:9][cH:8]1.CN(C)[CH:6]=[O:7]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[cH:8][cH:9][c:10]1[O:11][CH3:12] | CCc1cc(Br)ccc1OC.CN(C)C=O | CCc1cc(C=O)ccc1OC | null | null | C1CCOC1 | C-C Coupling | Bouveault aldehyde synthesis | 4664d189e1ff40b394aee0a7d0943c7bfc06c1f81f238cff6865649dda594153 | afd09ced98f25d311f21cc04ba6a50fe7e5516de47e17484683ded13d323b1b2 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-N(-C)-[CH;D2;+0:6]=[O;D1;H0:7]>>[O;D1;H0:7]=[CH;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 42.4 | [{"value": 42.0, "product": "C(C)C=1C=C(C=O)C=CC1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.4, "product": "C(C)C=1C=C(C=O)C=CC1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 1.5 | HOUR | A solution of 4-bromo-2-ethyl-1-methoxybenzene (J. Chem. Soc., Perkin Trans. 1, 1987, 1423; 2.13 g, 9.9 mmol) in THF (30 ml) was cooled to −78° C. A 1.6M solution of n-BuLi in hexane (7.42 ml, 11.9 mmol) was added slowly and the mixture was stirred for 1.5 h. at −78° C. The mixture was warmed slowly to −10° C. and subs... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Aldehyde | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | C1CCOC1 | -78 | 1.5 | CCc1cc(Br)ccc1OC.CN(C)C=O>C1CCOC1>CCc1cc(C=O)ccc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-76eafce56c074c27a5e5c2fbaad2ef64 | CCc1ccccc1O>>CCc1cc(C=O)ccc1O | C(C)C1=C(C=CC=C1)O.COC(Cl)Cl.Cl.Cl>>C(C)C=1C=C(C=O)C=CC1O | [CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:8][cH:9][c:10]1[OH:11]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[cH:8][cH:9][c:10]1[OH:11] | CCc1ccccc1O | CCc1cc(C=O)ccc1O | null | Cl[Ti](Cl)(Cl)Cl | C(Cl)Cl | Miscellaneous | OtherReaction | c25c41cbe22c67cd8a516e3f8fc0980bea758f12933876480aae20d5765822e2 | 3cccf922e74135722ee21a46ad7578302a8603e1f71d6f2113cd42de4ba0cf73 | c1ccccc1 | [c:1]:[c:2]:[cH;D2;+0:3]:[c:4]:[c:5]>>[O;D1;H0:6]=[C:7]-[c;H0;D3;+0:3](:[c:2]:[c:1]):[c:4]:[c:5] | 45 | [{"value": 45.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | TiCl4 (45.6 g, 238 mmol) was added slowly to a solution of 2-ethylphenol (15 g, 119 mmol) in CH2Cl2 (150 ml) was at 0° C. The mixture was warmed to room temperature and dichloromethyl methyl ether (18.3 ml, 200 mmol) was added (strong HCl evolution). The mixture was stirred for 4 h. at room temperature, subsequently co... | 10.6084/m9.figshare.5104873.v1 | null | null | Aldehyde | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | Cl[Ti](Cl)(Cl)Cl.C(Cl)Cl | null | 4 | CCc1ccccc1O>Cl[Ti](Cl)(Cl)Cl.C(Cl)Cl>CCc1cc(C=O)ccc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f233c8a7bce4492686f5cd122b3674c3 | CC(C)I.CCc1cc(C=O)ccc1O>>CCc1cc(C=O)ccc1OC(C)C | C(C)C=1C=C(C=O)C=CC1O.C(=O)([O-])[O-].[K+].[K+].C(C)(C)I>>C(C)C=1C=C(C=O)C=CC1OC(C)C | I[CH:12]([CH3:13])[CH3:14].[CH3:1][CH2:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[cH:8][cH:9][c:10]1[OH:11]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[cH:8][cH:9][c:10]1[O:11][CH:12]([CH3:13])[CH3:14] | CC(C)I.CCc1cc(C=O)ccc1O | CCc1cc(C=O)ccc1OC(C)C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | bff4876be49b448135c783dd3eeeb68ab3cc5bdc91beadda8a9095106cd5c747 | cf768afb66ed5041aefdce1fa6d1e40995a1ab7c4b4a4ca47544fe49ee1e629f | c1ccccc1 | I-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[CH;D3;+0:1](-[C;D1;H3:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 61 | [{"value": 61.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | A mixture of the 3-ethyl-4-hydroxy-benzaldehyde (7.8 g, 51.9 mmol) obtained in Example 179.1, K2CO3 (10.8 g, 78 mmol) and isopropyl iodide (7.86 ml, 78 mmol) was heated in DMF (65 ml) for 3 h. to 80° C. and subsequently stirred for 12 h. at room temperature. The mixture was poured into ice-cold 0.5M HCl and extracted w... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HI | CN(C)C=O | null | 12 | CC(C)I.CCc1cc(C=O)ccc1O>CN(C)C=O>CCc1cc(C=O)ccc1OC(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7f16407ba89f4b48a1dbdc4301c76647 | CCOC(=O)C(Nc1ccc(C#N)cc1)c1ccc(O)c(CC)c1.O=C1OCCO1>>CCOC(=O)C(Nc1ccc(C#N)cc1)c1ccc(OCCO)c(CC)c1 | C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=C(C=C1)O)CC.C1(OCCO1)=O>>C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=C(C=C1)OCCO)CC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]1)[c:16]1[cH:17][cH:18][c:19]([OH:20])[c:24]([CH2:25][CH3:26])[cH:27]1.O=C1O[CH2:21][CH2:22][O:23]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]1)[c:16]1[cH:17][cH:1... | CCOC(=O)C(Nc1ccc(C#N)cc1)c1ccc(O)c(CC)c1.O=C1OCCO1 | CCOC(=O)C(Nc1ccc(C#N)cc1)c1ccc(OCCO)c(CC)c1 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 34950df4dc1bc6c778d9cfa26c728e443e4886f7382a4283f1fbae4a959b8c37 | c6f5c5ba2d936b513bc18d6bcb095f40591aa3ba8700a9f5b8ecbbdd690dab72 | c1ccc(CNc2ccccc2)cc1 | O=C1-O-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-1.[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[OH;D1;+0:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 24.5 | [{"value": 24.0, "product": "C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=C(C=C1)OCCO)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 24.5, "product": "C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=C(C=C1)OCCO)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 155 | CELSIUS | null | null | A solution of the ethyl (RS)-(4-cyano-phenylamino)-(3-ethyl-4-hydroxy-phenyl)-acetate (400 mg, 1.23 mmol) described in Example 180.1, ethylene carbonate (110 mg, 1.23 mmol) and tetrabutylammonium bromide (264 mg, 1.23 mmol) in DMF (0.6 ml) was heated to 155° C. for 6 h. The reaction mixture was concentrated and the res... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Aromatic alcohol | Ether.Primary alcohol | C1COCO1 | null | c1ccccc1.c1ccccc1 | Other | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.CN(C)C=O | 155 | null | CCOC(=O)C(Nc1ccc(C#N)cc1)c1ccc(O)c(CC)c1.O=C1OCCO1>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.CN(C)C=O>CCOC(=O)C(Nc1ccc(C#N)cc1)c1ccc(OCCO)c(CC)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-42d7c47aba7846b8bd4af77b1781e2f6 | CC(C)N=C=O.CCOC(=O)C(Nc1ccc(C#N)cc1)c1ccc(N)c(CC)c1>>CCOC(=O)C(Nc1ccc(C#N)cc1)c1ccc(NC(=O)NC(C)C)c(CC)c1 | C(C)(C)N=C=O.C(C)(C)N=C=O.NC1=C(C=C(C=C1)C(C(=O)OCC)NC1=CC=C(C=C1)C#N)CC>>C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=C(C=C1)NC(=O)NC(C)C)CC | [C:21](=[O:22])=[N:23][CH:24]([CH3:25])[CH3:26].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]1)[c:16]1[cH:17][cH:18][c:19]([NH2:20])[c:27]([CH2:28][CH3:29])[cH:30]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]1... | CC(C)N=C=O.CCOC(=O)C(Nc1ccc(C#N)cc1)c1ccc(N)c(CC)c1 | CCOC(=O)C(Nc1ccc(C#N)cc1)c1ccc(NC(=O)NC(C)C)c(CC)c1 | null | null | C1CCOC1 | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc(CNc2ccccc2)cc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[N;H0;D2;+0:4]=[C;H0;D2;+0:5]=[O;D1;H0:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[NH;D2;+0:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 62.4 | [{"value": 62.0, "product": "C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=C(C=C1)NC(=O)NC(C)C)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.4, "product": "C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=C(C=C1)NC(=O)NC(C)C)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of isopropyl isocyanate (130 mg, 1.55 mmol) in THF (2 ml) was added to a solution of the ethyl (RS)-(4-amino-3-ethyl-phenyl)-(4-cyano-phenylamino)-acetate (500 mg, 1.55 mmol) described in Example 186.1 in THF (10 ml). The mixture was stirred overnight at room temperature. Thereafter, further isopropyl isocya... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccccc1 | null | C1CCOC1 | null | 8 | CC(C)N=C=O.CCOC(=O)C(Nc1ccc(C#N)cc1)c1ccc(N)c(CC)c1>C1CCOC1>CCOC(=O)C(Nc1ccc(C#N)cc1)c1ccc(NC(=O)NC(C)C)c(CC)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8d322502ccc248049f260c1b309c1daa | COc1cc(C)cc(C)c1.O=C1CCC(=O)N1Br>>COc1cc(C)cc(CBr)c1 | CC=1C=C(C=C(C1)C)OC.BrN1C(CCC1=O)=O.N(=NC(C#N)(C)C)C(C#N)(C)C>>BrCC1=CC(=CC(=C1)C)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH3:9])[cH:11]1.O=C1CCC(=O)N1[Br:10]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH2:9][Br:10])[cH:11]1 | COc1cc(C)cc(C)c1.O=C1CCC(=O)N1Br | COc1cc(C)cc(CBr)c1 | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 68 | [{"value": 68.0, "product": "BrCC1=CC(=CC(=C1)C)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.9, "product": "BrCC1=CC(=CC(=C1)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 3,5-dimethylanisole (13.60 g, 100 mmol), N-bromosuccinimide (18.35 g, 100 mmol) and 2,2′-azobis(2-methylpropionitrile) in CCl4 was heated under reflux for 1 h. The succinimide was filtered off, the filtrate was concentrated and the residue was chromatographed (SiO2, CH2Cl2hexane 1:4). There were obtaine... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | COc1cc(C)cc(C)c1.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>COc1cc(C)cc(CBr)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6ee0720ca9764c30ad0b0bdcf602e7e7 | COc1cc(C)cc(CBr)c1>>COc1cc(C)cc(C=O)c1 | [N+](=O)([O-])C(C)C.BrCC1=CC(=CC(=C1)C)OC.CC[O-].[Na+]>>COC=1C=C(C=O)C=C(C1)C | Br[CH2:9][c:8]1[cH:7][c:5]([CH3:6])[cH:4][c:3]([O:2][CH3:1])[cH:11]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH:9]=[O:10])[cH:11]1 | COc1cc(C)cc(CBr)c1 | COc1cc(C)cc(C=O)c1 | null | null | CCO | Functional Group Interconversion | OtherReaction | 58275b6d2237b60eec809a98524dd5509385280e465d11c6e117bcda9b506a40 | a6ad2c3ebd2a6d96768557808a4c04d3f87ec47615690d5a7123fffa828fc27a | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[O;D1;H0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 77.2 | [{"value": 77.0, "product": "COC=1C=C(C=O)C=C(C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.2, "product": "COC=1C=C(C=O)C=C(C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Nitropropane (6.77 ml, 71.3 mmol) and subsequently 1-bromomethyl-3-methoxy-5-methyl-benzene (14.6 g, 67.9 mmol) were added to a solution of NaOEt (4.72 g, 67.9 mmol) in EtOH (60 ml). The mixture was heated for 1.5 h. to 65° C. After cooling the colorless precipitate of filtered off and the filtrate was concentrated. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Aldehyde | null | null | c1ccccc1 | null | CCO | null | null | COc1cc(C)cc(CBr)c1>CCO>COc1cc(C)cc(C=O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cdee9b61f41e40f48a4e847666dd8773 | C=Cc1cc(OC)cc(C(Nc2ccc(C#N)cc2)C(=O)OCC)c1>>CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(CC)cc(OC)c1 | C1CCOC1.C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)C=C)OC>>C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)OC)CC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]1)[c:16]1[cH:17][c:18]([CH:19]=[CH2:20])[cH:21][c:22]([O:23][CH3:24])[cH:25]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]1)[c:16]1[cH:17][c:18]([CH2:19][CH3:20])[cH... | C=Cc1cc(OC)cc(C(Nc2ccc(C#N)cc2)C(=O)OCC)c1 | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(CC)cc(OC)c1 | null | [Pd] | CCO | Reduction | Hydrogenation (double to single) | 8276b4fb5ddc7d15dec6d92474e91e2dbb2fb8b81e5b5720762e5d89cb27aa69 | 1ccae9f2e86499601fc3421041ff4588c8e6fd53048e86c3b6ed12ae873609c0 | c1ccc(CNc2ccccc2)cc1 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[CH3;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 99.8 | [{"value": 99.0, "product": "C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)OC)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.8, "product": "C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)OC)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Pd-C (10%, 236 mg, 0.22 mmol) was added a solution of the ethyl (RS)-(4-cyano-phenylamino)-(3-methoxy-5-vinyl-phenyl)-acetate (1.495 g, 4.44 mmol) obtained in Example198.3 in EtOH (40 ml) and THF (4 ml) and the mixture was hydrogenated for 1 h. at room temperature. The reaction mixture was filtered, the filtrate was co... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | null | null | c1ccccc1.c1ccccc1 | null | [Pd].CCO | null | null | C=Cc1cc(OC)cc(C(Nc2ccc(C#N)cc2)C(=O)OCC)c1>[Pd].CCO>CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(CC)cc(OC)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5878529f0f764e53a242544318d2f37a | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(O)cc(CC)c1.OB(O)c1ccccc1>>CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(CC)cc(Oc2ccccc2)c1 | N1=CC=CC=C1.C1(=CC=CC=C1)B(O)O.C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)O)CC>>C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)OC1=CC=CC=C1)CC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]1)[c:16]1[cH:17][c:18]([CH2:19][CH3:20])[cH:21][c:22]([OH:23])[cH:30]1.OB(O)[c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]1... | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(O)cc(CC)c1.OB(O)c1ccccc1 | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(CC)cc(Oc2ccccc2)c1 | null | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-] | C(Cl)Cl | Heteroatom Alkylation and Arylation | Chan-Lam etherification | 6350c2e2ba8974cd73ee6523ede3b5f50e2acfea27607ceb21851222664d49c7 | 67a414b522726d7922fbf9add1aabcf2645110cf298c29aa16507aae85ca1b48 | c1ccc(NCc2cccc(Oc3ccccc3)c2)cc1 | O-B(-O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[O;H0;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9] | 81.4 | [{"value": 81.0, "product": "C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)OC1=CC=CC=C1)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.4, "product": "C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)OC1=CC=CC=C1)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 60 | HOUR | Copper(II) acetate (223 mg, 1.20 mmol), phenylboronic acid (164 mg, 1.32 mmol) and molecular sieve 4A were added to a solution of the ethyl (RS)-(4-cyano-phenylamino)-(3-ethyl-5-hydroxy-phenyl)-acetate (390 mg, 1.20 mmol) obtained in Example 200.1 in CH2Cl2 (12 ml). Pyridine (476 mg, 6.01 mmol) was added dropwise and t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Boronic acid | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HO-.B | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].C(Cl)Cl | null | 60 | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(O)cc(CC)c1.OB(O)c1ccccc1>C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].C(Cl)Cl>CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(CC)cc(Oc2ccccc2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2fb32836a8804ebc9cbdf07faac3397c | C1CCC2=NCCCN2CC1.CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(C)cc(N)c1.Clc1ncccn1>>CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(C)cc(N=C2CCCCCN2CCCNc2ncccn2)c1 | NC=1C=C(C=C(C1)C)C(C(=O)OCC)NC1=CC=C(C=C1)C#N.ClC1=NC=CC=N1.C(C)(C)N(CC)C(C)C.N12CCCCCC2=NCCC1>>C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)N=C1N(CCCCC1)CCCNC1=NC=CC=N1)C | [C:23]12=[N:29][CH2:30][CH2:31][CH2:32][N:33]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]1)[c:16]1[cH:17][c:18]([CH3:19])[cH:20][c:21]([NH2:22])[cH:40]1.Cl[c:34]1[n:35][cH:36][cH:37][cH:38][n:39]1>>[CH3:1][CH2:2][O:3][C:4]... | C1CCC2=NCCCN2CC1.CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(C)cc(N)c1.Clc1ncccn1 | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(C)cc(N=C2CCCCCN2CCCNc2ncccn2)c1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 6dd06b16dfa4e2389ea6c966029edcf0237b90d36d2d50cfdf7901e8bf03f0a0 | 554f2b1f51560c027b3299c2553740485ed806c9efc0f064d29380b1afd24651 | c1ccc(NCc2cccc(N=C3CCCCCN3CCCNc3ncccn3)c2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]1-[C:7]-[C:8]-[C:9]-[CH2;D2;+0:10]-[N;H0;D3;+0:11]2-[C:12]-[C:13]-[C:14]-[N;H0;D2;+0:15]=[C;H0;D3;+0:16]-1-2.[NH2;D1;+0:17]-[c:18](:[c:19]):[c:20]>>[c:19]:[c:18](-[N;H0;D2;+0:17]=[C;H0;D3;+0:16]1-[C:6]-[C:7]-[C:8]-[C:9]-[CH2;D2;+0:10]-[N;H0;D3;+0:15]-1-[C:14]-[C:13... | 23.2 | [{"value": 23.0, "product": "C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)N=C1N(CCCCC1)CCCNC1=NC=CC=N1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 23.2, "product": "C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)N=C1N(CCCCC1)CCCNC1=NC=CC=N1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of the ethyl (RS)-(3-amino-5-methyl-phenyl)-(4-cyano-phenylamino)-acetate (475 mg, 1.54 mmol) obtained in Example 216.3, 2-chloropyrimidine (400 mg, 3.38 mmol), diisopropylethylamine (317 μl, 1.85 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (276 μl, 1.85 mmol) in THF (4 ml) was heated under reflux for 2 h. ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine.Tertiary amine | Secondary amine.Tertiary amine | C1CCC2=NCCCN2CC1.c1cncnc1 | C1CCC[NH]CC1.c1cncnc1 | c1ccccc1.c1ccccc1.C1CCC[NH]CC1.c1cncnc1 | HCl | C1CCOC1 | null | null | C1CCC2=NCCCN2CC1.CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(C)cc(N)c1.Clc1ncccn1>C1CCOC1>CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(C)cc(N=C2CCCCCN2CCCNc2ncccn2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2ceb0dfc62834d8f89c64aca4dab949b | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(N)cc(CC)c1.NCCCl>>CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(CC)cc(N2CCNCC2)c1 | NC=1C=C(C=C(C1)CC)C(C(=O)OCC)NC1=CC=C(C=C1)C#N.Cl.ClCCN.ClCCN>>C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)N1CCNCC1)CC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]1)[c:16]1[cH:17][c:18]([CH2:19][CH3:20])[cH:21][c:22]([NH2:23])[cH:29]1.Cl[CH2:28][CH2:27][NH2:26]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]1)[c:16]1[cH:17][c:18]... | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(N)cc(CC)c1.NCCCl | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(CC)cc(N2CCNCC2)c1 | null | null | ClC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 0132580ea4de1fc5a1828a3ab88f9f88efc89c7c35dc5bc3087d0dce21d06a55 | d2ccf3d9894ea5a1e7cc00c6c38feafc35e176da83ec69f6db7ff5f3425328ec | c1ccc(NCc2cccc(N3CCNCC3)c2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[NH2;D1;+0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[c:6]:[c:5](-[N;H0;D3;+0:4]1-[C:8]-[C:9]-[NH;D2;+0:3]-[C:2]-[CH2;D2;+0:1]-1):[c:7] | 63.3 | [{"value": 63.0, "product": "C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)N1CCNCC1)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.3, "product": "C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)N1CCNCC1)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of the ethyl (RS)-(3-amino-5-ethyl-phenyl)-(4-cyano-phenylamino)-acetate (500 mg, 1.55 mmol) obtained in Example 223.4, bis-(2-chloroethylamine) hydrochloride (276 mg, 1.55 mmol) and chlorobenzene (5 ml) was heated under reflux for 18 h. The reaction mixture was concentrated and the residue was purified by ch... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine.Primary amine | Secondary amine.Tertiary amine | null | C1C[NH]CCN1 | c1ccccc1.c1ccccc1.C1C[NH]CCN1 | null | ClC1=CC=CC=C1 | null | null | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(N)cc(CC)c1.NCCCl>ClC1=CC=CC=C1>CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(CC)cc(N2CCNCC2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c10e5641a76c48b9955287bda5602d73 | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(N)cc(CC)c1.O=C(Cl)C1CCCC1>>CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(CC)cc(NC(=O)C2CCCC2)c1 | OS(=O)(=O)[O-].[K+].C1(CCCC1)C(=O)Cl.NC=1C=C(C=C(C1)CC)C(C(=O)OCC)NC1=CC=C(C=C1)C#N.C(C)(C)N(CC)C(C)C>>C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)CC)NC(=O)C1CCCC1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]1)[c:16]1[cH:17][c:18]([CH2:19][CH3:20])[cH:21][c:22]([NH2:23])[cH:31]1.Cl[C:24](=[O:25])[CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:... | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(N)cc(CC)c1.O=C(Cl)C1CCCC1 | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(CC)cc(NC(=O)C2CCCC2)c1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1cccc(CNc2ccccc2)c1)C1CCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[C:5] | 66.4 | [{"value": 66.0, "product": "C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)CC)NC(=O)C1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.4, "product": "C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)CC)NC(=O)C1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Cyclopentanecarbonyl chloride (0.104 ml, 0.85 mmol) was added dropwise at 0° C. to a solution of the ethyl (RS)-(3-amino-5-ethyl-phenyl)-(4-cyano-phenylamino)-acetate (250 mg, 0.772 mmol) obtained in Example 223.4 and diisopropylethylamine (0.146 ml, 0.85 mmol) in CH2Cl2 (5 ml). The reaction mixture was warmed slowly (... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.C1CCCC1 | HCl | C(Cl)Cl | null | null | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(N)cc(CC)c1.O=C(Cl)C1CCCC1>C(Cl)Cl>CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(CC)cc(NC(=O)C2CCCC2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a5479b8626d24080a354202a3727064c | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(N)cc(CC)c1.CN1CCC(=O)CC1>>CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(CC)cc(NC2CCN(C)CC2)c1 | [O-]S(=O)(=O)[O-].[Na+].[Na+].NC=1C=C(C=C(C1)CC)C(C(=O)OCC)NC1=CC=C(C=C1)C#N.CN1CCC(CC1)=O.C(=O)(O)[O-].[Na+]>>C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)NC1CCN(CC1)C)CC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]1)[c:16]1[cH:17][c:18]([CH2:19][CH3:20])[cH:21][c:22]([NH2:23])[cH:31]1.O=[C:24]1[CH2:25][CH2:26][N:27]([CH3:28])[CH2:29][CH2:30]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:... | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(N)cc(CC)c1.CN1CCC(=O)CC1 | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(CC)cc(NC2CCN(C)CC2)c1 | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 42e9e55fb09951ae64da272b20a0fe6708e6155493933c6a5b57bd203fbe3626 | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1ccc(NCc2cccc(NC3CCNCC3)c2)cc1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[NH;D2;+0:7]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1):[c:10] | 89 | [{"value": 89.0, "product": "C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)NC1CCN(CC1)C)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.6, "product": "C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)NC1CCN(CC1)C)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | Na2SO4 (1.09 g, 7.7 mmol) was added to a solution of the ethyl (RS)-(3-amino-5-ethyl-phenyl)-(4-cyano-phenylamino)-acetate (250 mg, 0.77 mmol) obtained in Example 223.4 and 1-methyl-4-piperidone (174 mg, 1.54 mmol) in acetic acid (5 ml) and the mixture was stirred for 15 min. at room temperature. The mixture was subseq... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | C1CC[NH]CC1 | C1CC[NH]CC1 | c1ccccc1.c1ccccc1.C1CC[NH]CC1 | Other | C(C)(=O)O | null | 0.25 | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(N)cc(CC)c1.CN1CCC(=O)CC1>C(C)(=O)O>CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(CC)cc(NC2CCN(C)CC2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b4b87759f5b84d4eb1f867937d51c9e7 | CCOc1cc(CO)cc(CO)c1>>CCOc1cc(C=O)cc(CO)c1 | C(C)OC=1C=C(C=C(C1)CO)CO>>C(C)OC=1C=C(C=O)C=C(C1)CO | [CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH2:7][OH:8])[cH:9][c:10]([CH2:11][OH:12])[cH:13]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]=[O:8])[cH:9][c:10]([CH2:11][OH:12])[cH:13]1 | CCOc1cc(CO)cc(CO)c1 | CCOc1cc(C=O)cc(CO)c1 | null | O=[Mn]=O.O=[Mn]=O | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccccc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 48 | [{"value": 48.0, "product": "C(C)OC=1C=C(C=O)C=C(C1)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.9, "product": "C(C)OC=1C=C(C=O)C=C(C1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 64 | HOUR | MnO2 (8.37 g, 96.3 mmol) was added to a solution of (3-ethoxy-5-hydroxymethyl-phenyl)-methanol (17.55 g, 96.3 mmol) in CH2Cl2 (175 ml) and the mixture was stirred for 64 h. at room temperature. Thereafter, further MnO2 (8.37 g, 96.3 mmol) was added and the mixture was stirred for 6 h. The mixture was-filtered over Celi... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1 | null | O=[Mn]=O.O=[Mn]=O.C(Cl)Cl | null | 64 | CCOc1cc(CO)cc(CO)c1>O=[Mn]=O.O=[Mn]=O.C(Cl)Cl>CCOc1cc(C=O)cc(CO)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f1467020b89f41ac9eae565ae6a8a8e3 | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(CO)cc(OCC)c1.CS(=O)(=O)Cl>>CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(COS(C)(=O)=O)cc(OCC)c1 | CS(=O)(=O)Cl.C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)CO)OCC.C(C)N(C(C)C)C(C)C>>C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)COS(=O)(=O)C)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]1)[c:16]1[cH:17][c:18]([CH2:19][OH:20])[cH:25][c:26]([O:27][CH2:28][CH3:29])[cH:30]1.Cl[S:21]([CH3:22])(=[O:23])=[O:24]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]1... | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(CO)cc(OCC)c1.CS(=O)(=O)Cl | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(COS(C)(=O)=O)cc(OCC)c1 | null | null | C1CCOC1 | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccc(CNc2ccccc2)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[OH;D1;+0:5]-[C:6]-[c:7]>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[O;H0;D2;+0:5]-[C:6]-[c:7] | null | [] | 0 | CELSIUS | 1.5 | HOUR | Methanesulphonyl chloride was added slowly at 0° C. to a solution of the ethyl (RS)-(4-cyano-phenylamino)-(3-ethoxy-5-hydroxymethyl-phenyl)-acetate (200 mg, 0.564 mmol) obtained in Example 234.2 and N-ethyldiisopropylamine (88 mg, 0.68 mmol) in THF (3 ml). The mixture was stirred for 1.5 h. at 0° C. and for 1.5 h. at r... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccccc1.c1ccccc1 | HCl | C1CCOC1 | 0 | 1.5 | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(CO)cc(OCC)c1.CS(=O)(=O)Cl>C1CCOC1>CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(COS(C)(=O)=O)cc(OCC)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-19ef38f4b1a54aa787b9c5d291833e41 | C1CCNC1.CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(COS(C)(=O)=O)cc(OCC)c1>>CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(CN2CCCC2)cc(OCC)c1 | C(C)N(C(C)C)C(C)C.N1CCCC1.C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)COS(=O)(=O)C)OCC>>C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)CN1CCCC1)OCC | [NH:20]1[CH2:21][CH2:22][CH2:23][CH2:24]1.CS(=O)(=O)O[CH2:19][c:18]1[cH:17][c:16]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[NH:7][c:8]2[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]2)[cH:30][c:26]([O:27][CH2:28][CH3:29])[cH:25]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:... | C1CCNC1.CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(COS(C)(=O)=O)cc(OCC)c1 | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(CN2CCCC2)cc(OCC)c1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Alkylation of amines | d27d68bc3d43f6d66a205fa71d9985c3ff34906c317c31aac4632a55b7f79861 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | c1ccc(NCc2cccc(CN3CCCC3)c2)cc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]1-[C:6]-[C:7]-[C:8]-[NH;D2;+0:9]-1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:9]1-[C:5]-[C:6]-[C:7]-[C:8]-1):[c:4] | 73.5 | [{"value": 73.0, "product": "C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)CN1CCCC1)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.5, "product": "C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)CN1CCCC1)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | N-Ethyldiisopropylamine (132 mg, 1.02 mmol) and pyrrolidine (145 mg, 2.04 mmol) were added to a solution of the ethyl (RS)-(4-cyano-phenylamino)-(3-ethoxy-5-methane-sulphonyloxymethyl-phenyl)-acetate (221 mg, 0.511 mmol) obtained in Example 234.3 in THF (2 ml) and the mixture was stirred for 1 h. at room temperature. T... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.c1ccccc1.C1CC[NH]C1 | MsOH.HO- | C1CCOC1 | null | 1 | C1CCNC1.CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(COS(C)(=O)=O)cc(OCC)c1>C1CCOC1>CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(CN2CCCC2)cc(OCC)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-027a27fe5520401983f049bef66f6890 | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(C=O)cc(OCC)c1.Nc1ccccc1N>>CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(OCC)cc(-c2nc3ccccc3[nH]2)c1 | O.ClC=1C(C(=C(C(C1Cl)=O)C#N)C#N)=O.C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)C=O)OCC.C1(=C(C=CC=C1)N)N>>N1C(=NC2=C1C=CC=C2)C=2C=C(C=C(C2)OCC)C(C(=O)OCC)NC2=CC=C(C=C2)C#N | O=[CH:24][c:23]1[cH:22][c:18]([O:19][CH2:20][CH3:21])[cH:17][c:16]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[NH:7][c:8]2[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]2)[cH:33]1.[NH2:25][c:26]1[cH:27][cH:28][cH:29][cH:30][c:31]1[NH2:32]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]#[N:1... | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(C=O)cc(OCC)c1.Nc1ccccc1N | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(OCC)cc(-c2nc3ccccc3[nH]2)c1 | null | null | C(C)#N | Aromatic Heterocycle Formation | Benzimidazole aldehyde | 357211f0cea48f6066cc617c063d8f639b186739754abf69a9bef955d42b7d06 | 947e8e758a50553bad3d8f39fd1540e5051c4c73055f7a5a9da00894523e8ba0 | c1ccc(NCc2cccc(-c3nc4ccccc4[nH]3)c2)cc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10](-[NH2;D1;+0:11]):[c:12]>>[c:6]:[c:5]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:7]:[c:8](:[c:9]):[c:10](:[c:12]):[nH;D2;+0:11]:1):[c:3]:[c:4] | 30 | [{"value": 30.0, "product": "N1C(=NC2=C1C=CC=C2)C=2C=C(C=C(C2)OCC)C(C(=O)OCC)NC2=CC=C(C=C2)C#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A solution of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in acetonitrile (1.5 ml) was added dropwise very slowly (2 h.) to a solution of the ethyl (RS)-(4-cyano-phenylamino)-(3-ethoxy-5-formyl-phenyl)-acetate (460 mg, 1.305 mmol) obtained in Example 244.1 and 1,2-phenylenediamine in acetonitrile (2 ml). The reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine.Primary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccccc1.c1ccccc1.c1ccc2[nH]cnc2c1 | HO- | C(C)#N | null | 4 | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(C=O)cc(OCC)c1.Nc1ccccc1N>C(C)#N>CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(OCC)cc(-c2nc3ccccc3[nH]2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a0ae641014774180a42e4984ee80b71d | C=Cc1cc(OCC)cc(C(Nc2ccc(C#N)cc2)C(=O)OCC)c1.CC#N.N#[O+]>>CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(OCC)cc(-c2cnc(C)n2O)c1 | C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)C=C)OCC.[B-](F)(F)(F)F.N#[O+].C(C)#N.C(C)#N>>C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)C=1N(C(=NC1)C)O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]1)[c:16]1[cH:17][c:18]([O:19][CH2:20][CH3:21])[cH:22][c:23]([CH:24]=[CH2:25])[cH:31]1.[N:26]#[C:27][CH3:28].[N:29]#[O+:30]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:1... | C=Cc1cc(OCC)cc(C(Nc2ccc(C#N)cc2)C(=O)OCC)c1.CC#N.N#[O+] | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(OCC)cc(-c2cnc(C)n2O)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 07556c7c072f7dcf0b02735bede0382cd836c611811322b8b7d7b573bf89d36a | a40a1c94e5aadd9c36688947bee6dbd19c8f45165d71852d1b1864204cbb0805 | c1ccc(NCc2cccc(-c3cnc[nH]3)c2)cc1 | [C;D1;H3:1]-[C;H0;D2;+0:2]#[N;H0;D1;+0:3].[CH2;D1;+0:4]=[CH;D2;+0:5]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10].[N;H0;D1;+0:11]#[O+;H0;D1:12]>>[C;D1;H3:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[n;H0;D3;+0:11]:1-[OH;D1;+0:12] | 38 | [{"value": 38.0, "product": "C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)C=1N(C(=NC1)C)O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1.5 | HOUR | A solution of the ethyl (RS)-(4-cyano-phenylamino)-(3-ethoxy-5-vinyl-phenyl)-acetate (300 mg, 0.856 mmol) obtained in Example 236.2 in acetonitrile (2 ml) was slowly added dropwise at −30° C. to a solution of nitrosyl tetrafluoroborate (112 mg, 0.942 mmol) in acetonitrile (3 ml). The mixture was stirred for 2 h. at 0° ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Vinyl | null | null | c1c[nH]cn1 | c1ccccc1.c1ccccc1.c1c[nH]cn1 | null | null | 0 | 1.5 | C=Cc1cc(OCC)cc(C(Nc2ccc(C#N)cc2)C(=O)OCC)c1.CC#N.N#[O+]>>CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(OCC)cc(-c2cnc(C)n2O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d7fcac670a6c4fc5aef22f9d461d86f1 | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(OCC)cc(-c2cnc(C)n2O)c1>>CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(OCC)cc(-c2cnc(C)[nH]2)c1 | C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)C=1N(C(=NC1)C)O)OCC.C(=O)(O)[O-].[Na+]>>C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)C=1NC(=NC1)C)OCC | O[n:29]1[c:24](-[c:23]2[cH:22][c:18]([O:19][CH2:20][CH3:21])[cH:17][c:16]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[NH:7][c:8]3[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]3)[cH:30]2)[cH:25][n:26][c:27]1[CH3:28]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]1)[c:1... | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(OCC)cc(-c2cnc(C)n2O)c1 | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(OCC)cc(-c2cnc(C)[nH]2)c1 | null | null | O.CO | Reduction | OtherReaction | 69bcfbf359d84722baf1f445ec3e8dc346e40c6c428ecc128f7b55baec3099f0 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc(NCc2cccc(-c3cnc[nH]3)c2)cc1 | O-[n;H0;D3;+0:1]1:[c:2](-[c:3]):[c:4]:[#7;a:5]:[c:6]:1-[C;D1;H3:7]>>[C;D1;H3:7]-[c:6]1:[#7;a:5]:[c:4]:[c:2](-[c:3]):[nH;D2;+0:1]:1 | 15 | [{"value": 15.0, "product": "C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)C=1NC(=NC1)C)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 14.6, "product": "C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=CC(=CC(=C1)C=1NC(=NC1)C)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A 20% solution of TiCl3 in H2O was added dropwise at 0° C. to a solution of the ethyl (RS)-(4-cyano-phenylamino)-[3-ethoxy-5-(3-hydroxy-2-methyl-3H-imidazol-4-yl)-phenyl]-acetate (355 mg, 0.844 mmol) obtained in Example 247.1 in MeOH (4.2 ml). The mixture was stirred for 3 h. at room temperature, subsequently poured in... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1cnc[nH]1 | c1c[nH]cn1 | c1ccccc1.c1ccccc1.c1c[nH]cn1 | Other | O.CO | null | 3 | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(OCC)cc(-c2cnc(C)n2O)c1>O.CO>CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(OCC)cc(-c2cnc(C)[nH]2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-43162e86cd30475ea1f3e4994c210407 | CC(C)(C)[Si](C)(C)Oc1cc(C=O)c(F)c(O[Si](C)(C)C(C)(C)C)c1.CI.CN(C)C=O>>COc1cc(C=O)c(F)c(OC)c1 | C(C)(C)(C)[Si](OC=1C(=C(C=O)C=C(C1)O[Si](C)(C)C(C)(C)C)F)(C)C.[F-].[K+].CI.CN(C)C=O>>FC1=C(C=O)C=C(C=C1OC)OC | CC(C)(C)[Si](C)(C)[O:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[c:8]([F:9])[c:10]([O:11][Si](C)(C)C(C)(C)C)[cH:13]1.I[CH3:1].CN(C=O)[CH3:12]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[c:8]([F:9])[c:10]([O:11][CH3:12])[cH:13]1 | CC(C)(C)[Si](C)(C)Oc1cc(C=O)c(F)c(O[Si](C)(C)C(C)(C)C)c1.CI.CN(C)C=O | COc1cc(C=O)c(F)c(OC)c1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | b4cfc5934b6bc275832ea07f692e4d194d62061931bbd6ffc0a8ebf5b52c47fe | 2418c2f5a07557706a665a40b21c54524b317749f9595e3a8ed8b9caf7bd6436 | c1ccccc1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5](-[O;H0;D2;+0:6]-[Si](-C)(-C)-C(-C)(-C)-C):[c:7].C-N(-[CH3;D1;+0:8])-C=O.I-[CH3;D1;+0:9]>>[CH3;D1;+0:8]-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5](-[O;H0;D2;+0:6]-[CH3;D1;+0:9]):[c:7] | 60 | [{"value": 60.0, "product": "FC1=C(C=O)C=C(C=C1OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A mixture of the 3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-fluoro-benzaldehyde (3.0 g, 7.8 mmol) obtained in Example 251.1, potassium fluoride (1.81 g, 31.2 mmol), methyl iodide (1.17 ml, 18.7 mmol) and DMF (25 ml) was stirred for 2 h. at room temperature. Water (25 ml) was added and the mixture was extracted with die... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.TMS ether protective group.TMS ether protective group | Ether.Ether | null | null | c1ccccc1 | HI | O | null | 2 | CC(C)(C)[Si](C)(C)Oc1cc(C=O)c(F)c(O[Si](C)(C)C(C)(C)C)c1.CI.CN(C)C=O>O>COc1cc(C=O)c(F)c(OC)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0aa7293ccaec4e46a42850f7bfed4364 | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(C(C)C)c(OC(C)C)cc1C.NC(=O)CI>>CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(C(C)C)c(OCC(N)=O)cc1C | B(Br)(Br)Br.OS(=O)(=O)[O-].[K+].C(=O)([O-])[O-].[Cs+].[Cs+].ICC(=O)N.C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=C(C=C(C(=C1)C(C)C)OC(C)C)C>>C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=C(C=C(C(=C1)C(C)C)OCC(N)=O)C | CC(C)[O:23][c:22]1[c:18]([CH:19]([CH3:20])[CH3:21])[cH:17][c:16]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[NH:7][c:8]2[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]2)[c:29]([CH3:30])[cH:28]1.I[CH2:24][C:25]([NH2:26])=[O:27]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][c:8]1[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][c... | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(C(C)C)c(OC(C)C)cc1C.NC(=O)CI | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(C(C)C)c(OCC(N)=O)cc1C | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 9fcb28d714627a82c73fec5229176c30a914ef8ae51774a2cb8b9b86d834ab53 | 969a4609e178674696657c590a647839ca01abd1f90b8f0c9e475b1d6507651b | c1ccc(CNc2ccccc2)cc1 | C-C(-C)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].I-[CH2;D2;+0:5]-[C:6](-[N;D1;H2:7])=[O;D1;H0:8]>>[N;D1;H2:7]-[C:6](=[O;D1;H0:8])-[CH2;D2;+0:5]-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4] | 73 | [{"value": 73.0, "product": "C(#N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=C(C=C(C(=C1)C(C)C)OCC(N)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 15 | MINUTE | The ethyl (RS)-(4-cyano-phenylamino)-(4-isopropoxy-5-isopropyl-2-methyl-phenyl)-acetate (921 mg, 2.34 mmol) obtained in Example 254.2 was dissolved in CH2Cl2 and cooled to −78° C. A 1M solution of BBr3 in CH2Cl2 (9.4 ml, 9.4 mmol) was slowly added dropwise. After 15 min. the reaction mixture was left to warm to 0° C. a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether | null | null | c1ccccc1.c1ccccc1 | HI | C(Cl)Cl | -78 | 0.25 | CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(C(C)C)c(OC(C)C)cc1C.NC(=O)CI>C(Cl)Cl>CCOC(=O)C(Nc1ccc(C#N)cc1)c1cc(C(C)C)c(OCC(N)=O)cc1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-81af69bf9b24402a94daaf231b496eaf | CC(C)(C)OC(=O)COc1c(Cl)cc(Cl)cc1C=O.N=C(NO)c1ccc(N)cc1.[C-]#[N+]Cc1ccccc1>>COC(=O)C(Nc1ccc(C(=N)NO)cc1)c1cc(Cl)cc(Cl)c1OCC(=O)OC(C)(C)C | ClC1=C(OCC(=O)OC(C)(C)C)C(=CC(=C1)Cl)C=O.NC1=CC=C(C(=N)NO)C=C1.C(C1=CC=CC=C1)[N+]#[C-]>>C(C)(C)(C)OC(=O)COC1=C(C=C(C=C1Cl)Cl)C(C(=O)OC)NC1=CC=C(C=C1)C(NO)=N | [O:2]=[CH:3][c:17]1[cH:18][c:19]([Cl:20])[cH:21][c:22]([Cl:23])[c:24]1[O:25][CH2:26][C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33].[NH2:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[NH:12])[NH:13][OH:14])[cH:15][cH:16]1.c1ccc([CH2:5][N+]#[C-:1])cc1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([NH:6][c:7]1[cH:8][cH:9][c:10]([C:11](=... | CC(C)(C)OC(=O)COc1c(Cl)cc(Cl)cc1C=O.N=C(NO)c1ccc(N)cc1.[C-]#[N+]Cc1ccccc1 | COC(=O)C(Nc1ccc(C(=N)NO)cc1)c1cc(Cl)cc(Cl)c1OCC(=O)OC(C)(C)C | null | null | null | C-C Coupling | OtherReaction | 62b53aa4bfe460cdf1ebf73b9d33b21367f70d033a1e2d3163e05cade1ace616 | 85c87be0bad049b90586d8941e1842b6bbb624f1a5fcdfd7d77b4aad240e4217 | c1ccc(CNc2ccccc2)cc1 | [#8:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[CH;D2;+0:5]=[O;H0;D1;+0:6]):[c:7]:[c:8].[C-;H0;D1:9]#[N+]-[CH2;D2;+0:10]-c1:c:c:c:c:c:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#8:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[CH;D3;+0:10](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14])-[C;H0;D3;+0:5](=[O;D1;H0:15])-[O;H0;D2;+0:6]-[CH3;D1;+0:9]):[c:7]... | null | [] | null | null | null | null | In analogy to Example 1.1., tert-butyl (2,4-dichloro-6-formyl-phenoxy)-acetate was reacted with 4-amino-N-hydroxybenzamidine and benzyl isonitrile. There was obtained methyl (RS)-(2-tert-butoxycarbonylmethoxy-3,5-dichloro-phenyl)-[4-(N-hydroxycarbamimidoyl)-phenylamino]-acetate; MS (ISP) m/z 498.2 (M+H)+, 520.2 (M+Na)+... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Isocyanide.Primary amine | Ester.Secondary amine | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Other | null | null | null | CC(C)(C)OC(=O)COc1c(Cl)cc(Cl)cc1C=O.N=C(NO)c1ccc(N)cc1.[C-]#[N+]Cc1ccccc1>>COC(=O)C(Nc1ccc(C(=N)NO)cc1)c1cc(Cl)cc(Cl)c1OCC(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c14f4340f9aa4757b8c21fec29ca5528 | COC(=O)C(Nc1ccc(C(=N)NO)cc1)c1cc(Cl)cc(Cl)c1OCC(=O)OC(C)(C)C>>CC(C)(C)OC(=O)COc1c(Cl)cc(Cl)cc1C(Nc1ccc(C(=N)NO)cc1)C(=O)O | C([O-])([O-])=O.[Li+].[Li+].C(C)(C)(C)OC(=O)COC1=C(C=C(C=C1Cl)Cl)C(C(=O)OC)NC1=CC=C(C=C1)C(NO)=N>>C(C)(C)(C)OC(=O)COC1=C(C=C(C=C1Cl)Cl)C(C(=O)O)NC1=CC=C(C=C1)C(NO)=N | C[O:32][C:30]([CH:18]([c:17]1[c:10]([O:9][CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:11]([Cl:12])[cH:13][c:14]([Cl:15])[cH:16]1)[NH:19][c:20]1[cH:21][cH:22][c:23]([C:24](=[NH:25])[NH:26][OH:27])[cH:28][cH:29]1)=[O:31]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][O:9][c:10]1[c:11]([Cl:12])[cH:... | COC(=O)C(Nc1ccc(C(=N)NO)cc1)c1cc(Cl)cc(Cl)c1OCC(=O)OC(C)(C)C | CC(C)(C)OC(=O)COc1c(Cl)cc(Cl)cc1C(Nc1ccc(C(=N)NO)cc1)C(=O)O | null | null | O.C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(CNc2ccccc2)cc1 | 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] | 83.5 | [{"value": 83.5, "product": "C(C)(C)(C)OC(=O)COC1=C(C=C(C=C1Cl)Cl)C(C(=O)O)NC1=CC=C(C=C1)C(NO)=N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 3.7 g of finely powdered lithium carbonate were added to a solution of 1.96 g of methyl (RS)-(2-tert-butoxycarbonylmethoxy-3,5-dichloro-phenyl)-[4-(N-hydroxycarbamimidoyl)-phenylamino]-acetate (see Example 276.2) in 200 ml of THF and 100 ml of water. The suspension was stirred for 8 hours at 55–60° C. The reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | O.C1CCOC1 | null | 8 | COC(=O)C(Nc1ccc(C(=N)NO)cc1)c1cc(Cl)cc(Cl)c1OCC(=O)OC(C)(C)C>O.C1CCOC1>CC(C)(C)OC(=O)COc1c(Cl)cc(Cl)cc1C(Nc1ccc(C(=N)NO)cc1)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fc9aa4af912d4bc388be553067e52402 | C=CCI.O=Cc1cc(Cl)cc(Cl)c1O>>C=CCOc1c(Cl)cc(Cl)cc1C=O | ClC1=C(C(C=O)=CC(=C1)Cl)O.C(C=C)I>>C(C=C)OC1=C(C=O)C=C(C=C1Cl)Cl | I[CH2:3][CH:2]=[CH2:1].[OH:4][c:5]1[c:6]([Cl:7])[cH:8][c:9]([Cl:10])[cH:11][c:12]1[CH:13]=[O:14]>>[CH2:1]=[CH:2][CH2:3][O:4][c:5]1[c:6]([Cl:7])[cH:8][c:9]([Cl:10])[cH:11][c:12]1[CH:13]=[O:14] | C=CCI.O=Cc1cc(Cl)cc(Cl)c1O | C=CCOc1c(Cl)cc(Cl)cc1C=O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | I-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[O;D1;H0:4]=[C:5]-[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[C;D1;H2:3]=[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:7](:[c:9]):[c:6]-[C:5]=[O;D1;H0:4] | 90.9 | [{"value": 90.9, "product": "C(C=C)OC1=C(C=O)C=C(C=C1Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | null | null | A solution of 5.0 g of 3,5-dichlorosalicylaldehyde in 50 ml of DMF was treated with 3.23 g of potassium-tert.-butylate and 6.6 g of allyl iodide and stirred under argon at 65° C. After 2 hours the reaction mixture was concentrated, treated with ice-water and extracted with ethyl acetate. The organic phases were dried o... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HI | CN(C)C=O | 65 | null | C=CCI.O=Cc1cc(Cl)cc(Cl)c1O>CN(C)C=O>C=CCOc1c(Cl)cc(Cl)cc1C=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-15d64ebc0267416093291a352eeb1610 | C=CCOc1c(Cl)cc(Cl)cc1C(Nc1ccc(C(=N)N)cc1)C(=O)OCC>>CCOC(=O)C(Nc1ccc(C(=N)N)cc1)c1cc(Cl)cc(Cl)c1O | Cl.C(C=C)OC1=C(C=C(C=C1Cl)Cl)C(C(=O)OCC)NC1=CC=C(C=C1)C(N)=N.[H][H]>>Cl.C(N)(=N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=C(C(=CC(=C1)Cl)Cl)O | C=CC[O:25][c:24]1[c:17]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[NH:7][c:8]2[cH:9][cH:10][c:11]([C:12](=[NH:13])[NH2:14])[cH:15][cH:16]2)[cH:18][c:19]([Cl:20])[cH:21][c:22]1[Cl:23]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([NH:7][c:8]1[cH:9][cH:10][c:11]([C:12](=[NH:13])[NH2:14])[cH:15][cH:16]1)[c:17]1[cH:18][c:19]([Cl:2... | C=CCOc1c(Cl)cc(Cl)cc1C(Nc1ccc(C(=N)N)cc1)C(=O)OCC | CCOC(=O)C(Nc1ccc(C(=N)N)cc1)c1cc(Cl)cc(Cl)c1O | null | [Pt](=O)=O | C(C)O | Deprotection | OtherReaction | f4ce7d74a5657f3965368abbd2a5625bd267a6dbb505c3662fc1651562bbb4b7 | f8c57e7b4051fe7b27e1c2c4334ce9a197aecc4fa76b491933cdc533ef041581 | c1ccc(CNc2ccccc2)cc1 | C=C-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 197.2 | [{"value": 197.2, "product": "Cl.C(N)(=N)C1=CC=C(C=C1)NC(C(=O)OCC)C1=C(C(=CC(=C1)Cl)Cl)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 300 mg of ethyl (RS)-(2-allyloxy-3,5-dichloro-phenyl)-(4-carbamimidoyl-phenylamino)-acetate hydrochloride (1:1) (see Example 293.3) in 5 ml of ethanol was treated with hydrogen in ther presence of a catalytic amount of platinum dioxide for 45 minutes while stirring. The reaction mixture was suction filter... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Allyl | Aromatic alcohol | null | null | c1ccccc1.c1ccccc1 | Other | [Pt](=O)=O.C(C)O | null | null | C=CCOc1c(Cl)cc(Cl)cc1C(Nc1ccc(C(=N)N)cc1)C(=O)OCC>[Pt](=O)=O.C(C)O>CCOC(=O)C(Nc1ccc(C(=N)N)cc1)c1cc(Cl)cc(Cl)c1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3b47bc3ffb574151b68faf320d376a5a | CCc1ccccc1O.II>>CCc1cc(I)ccc1O | C(C)C1=C(C=CC=C1)O.II>>C(C)C1=C(C=CC(=C1)I)O | [CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:7][cH:8][c:9]1[OH:10].I[I:6]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([I:6])[cH:7][cH:8][c:9]1[OH:10] | CCc1ccccc1O.II | CCc1cc(I)ccc1O | null | [Cu](Cl)Cl | ClC1=CC=CC=C1 | Functional Group Interconversion | OtherReaction | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | I-[I;H0;D1;+0:1].[c:2]:[c:3]:[cH;D2;+0:4]:[c:5]:[c:6]>>[I;H0;D1;+0:1]-[c;H0;D3;+0:4](:[c:3]:[c:2]):[c:5]:[c:6] | null | [] | null | null | null | null | A solution of 119.9 ml of 2-ethylphenol in 500 ml of chlorobenzene was treated with 126.9 g of iodine and 134.5 g of copper(II) chloride and stirred under reflux for 5.5 hours. After cooling the reaction mixture was filtered and the residue was washed with methylene chloride. The combined filtrates were washed with aqu... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HI | [Cu](Cl)Cl.ClC1=CC=CC=C1 | null | null | CCc1ccccc1O.II>[Cu](Cl)Cl.ClC1=CC=CC=C1>CCc1cc(I)ccc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4c8981cb9c0d43b4a7d0eaad5e4383e4 | BrC1CC1.CCc1cc(I)ccc1OCOC>>CCc1cc(C2CC2)ccc1OCOC | [Cl-].[NH4+].C1(CC1)[Mg]Br.[Mg].C1(CC1)Br.C(C)C1=C(C=CC(=C1)I)OCOC>>C1(CC1)C1=CC(=C(C=C1)OCOC)CC | Br[CH:6]1[CH2:7][CH2:8]1.I[c:5]1[cH:4][c:3]([CH2:2][CH3:1])[c:11]([O:12][CH2:13][O:14][CH3:15])[cH:10][cH:9]1>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([CH:6]2[CH2:7][CH2:8]2)[cH:9][cH:10][c:11]1[O:12][CH2:13][O:14][CH3:15] | BrC1CC1.CCc1cc(I)ccc1OCOC | CCc1cc(C2CC2)ccc1OCOC | null | null | C1(=CC=CC=C1)C.C1CCOC1 | C-C Coupling | Negishi | a6a0a942700abd19dde9618ba99c0b96c2611472c76451f64710e85e20af9cb7 | bcd52134d05aa16cad424a20dc0b6e109ade5c5544b8a13a8584b7716080b109 | c1ccc(C2CC2)cc1 | Br-[CH;D3;+0:1]1-[C:2]-[C:3]-1.I-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8]>>[c:8]:[c:7]:[c;H0;D3;+0:4](-[CH;D3;+0:1]1-[C:2]-[C:3]-1):[c:5]:[c:6] | null | [] | null | null | 2 | HOUR | A solution of cyclopropylmagnesium bromide, freshly prepared from 2.49 g of magnesium and 13.3 g of cyclopropyl bromide in 40 ml of THF, was treated with 1.2 g of bistriphenylphosphine-nickel chloride and at 35–45° C. within 20 minutes with a solution of 20.8 g of 2-ethyl-4-iodo-1-methoxymethoxy-benzene in 40 ml of tol... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary halide | null | C1CC1.c1ccccc1 | c1ccccc1.C1CC1 | c1ccccc1.C1CC1 | Br-.I- | C1(=CC=CC=C1)C.C1CCOC1 | null | 2 | BrC1CC1.CCc1cc(I)ccc1OCOC>C1(=CC=CC=C1)C.C1CCOC1>CCc1cc(C2CC2)ccc1OCOC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4f91d52ba0f449b693806997400023fa | CCc1cc(C2CC2)ccc1OCOC>>CCc1cc(C2CC2)ccc1O | C1(CC1)C1=CC(=C(C=C1)OCOC)CC>>C1(CC1)C1=CC(=C(C=C1)O)CC | COC[O:12][c:11]1[c:3]([CH2:2][CH3:1])[cH:4][c:5]([CH:6]2[CH2:7][CH2:8]2)[cH:9][cH:10]1>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([CH:6]2[CH2:7][CH2:8]2)[cH:9][cH:10][c:11]1[OH:12] | CCc1cc(C2CC2)ccc1OCOC | CCc1cc(C2CC2)ccc1O | null | null | C(C)(=O)O | Reduction | OtherReaction | 92f30feec6876d2f8c7439342f0f488fd5811a8fdb3b3cb63d7289bd57242715 | 3165f563067f8d27bb50b0da034e3e854d1ead7f745de7cf575f7ca4cf677789 | c1ccc(C2CC2)cc1 | C-O-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 92.2 | [{"value": 92.2, "product": "C1(CC1)C1=CC(=C(C=C1)O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 12.0 g of 4-cyclopropyl-2-ethyl-1-methoxymethoxy-benzene in 240 ml of 2N acetic acid was stirred for 24 hours at 90° C. The reaction mixture was poured into ice-water and extracted with dichloromethane. The organic phases were washed with water, saturated aqueous sodium bicarbonate solution and sodium chl... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol | null | null | c1ccccc1.C1CC1 | HO- | C(C)(=O)O | null | null | CCc1cc(C2CC2)ccc1OCOC>C(C)(=O)O>CCc1cc(C2CC2)ccc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3366d76849714bed87f955ee6aad4579 | CCc1ccc(O)c(C=O)c1.[I-]>>CCc1cc(I)c(O)c(C=O)c1 | C(C)C1=CC=C(C(C=O)=C1)O.[I-].[Na+].ClN>>C(C)C=1C=C(C(=C(C=O)C1)O)I | [CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:7]([OH:8])[c:9]([CH:10]=[O:11])[cH:12]1.[I-:6]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([I:6])[c:7]([OH:8])[c:9]([CH:10]=[O:11])[cH:12]1 | CCc1ccc(O)c(C=O)c1.[I-] | CCc1cc(I)c(O)c(C=O)c1 | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | [I-;H0;D0:1].[O;D1;H0:2]=[C:3]-[c:4]:[c:5](-[O;D1;H1:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[I;H0;D1;+0:1]-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:5](-[O;D1;H1:6]):[c:4]-[C:3]=[O;D1;H0:2] | 83 | [{"value": 83.0, "product": "C(C)C=1C=C(C(=C(C=O)C1)O)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 30.0 g of 5-ethyl-salicylaldehyde (Reg. No. 52411-35-5) in 500 ml of DMF was treated with 36.0 g of sodium iodide and 67.6 g of Chloroamine T and stirred for one hour at room temperature. The reaction mixture was concentrated in a high vacuum, poured into ice-water, made acid with 2N hydrochloric acid and... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | CN(C)C=O | null | 1 | CCc1ccc(O)c(C=O)c1.[I-]>CN(C)C=O>CCc1cc(I)c(O)c(C=O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0018e7c764c94e929c9a3b0168b96f0d | C=CCN=CC(C)CC=C>>C=CCNCC(C)CC=C | C(C=C)N.C(C=C)N=CC(CC=C)C.[BH4-].[Na+].CC(C=O)CC=C.C(C)OC(C(CC=C)C)=O.CC(C)C[AlH]CC(C)C>>C(C=C)NCC(CC=C)C | [CH2:1]=[CH:2][CH2:3][N:4]=[CH:5][CH:6]([CH3:7])[CH2:8][CH:9]=[CH2:10]>>[CH2:1]=[CH:2][CH2:3][NH:4][CH2:5][CH:6]([CH3:7])[CH2:8][CH:9]=[CH2:10] | C=CCN=CC(C)CC=C | C=CCNCC(C)CC=C | null | null | C(Cl)Cl.CO | Reduction | OtherReaction | d4a3c3af6b6e3a46274c741e9feddcd7af52a8fba8716af75123ec94a3d0151d | 469efbca661320a0d72c32f19625ec46edbc3ad7686cf46fdd0591eb136a8d7e | null | [C;D1;H2:1]=[C:2]-[C:3]-[C:4](-[C;D1;H3:5])-[CH;D2;+0:6]=[N;H0;D2;+0:7]-[C:8]-[C:9]=[C;D1;H2:10]>>[C;D1;H2:1]=[C:2]-[C:3]-[C:4](-[C;D1;H3:5])-[CH2;D2;+0:6]-[NH;D2;+0:7]-[C:8]-[C:9]=[C;D1;H2:10] | 48 | [{"value": 48.0, "product": "C(C=C)NCC(CC=C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.0, "product": "C(C=C)NCC(CC=C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 2-methyl-pent-4-enoic acid ethyl ester (7.1 g, 50 mmol) was added dropwise a solution of DIBAL (1.0 M in hexanes, 75 ml) at −78 C. over 1.0 h. After the addition, the reaction mixture was stirred at −78 C. for another hour. The reaction was quenched with saturated NH4Cl (10 ml) and 4% HCl, then was ext... | 10.6084/m9.figshare.5104873.v1 | null | Substituted imine | Secondary amine | null | null | null | null | C(Cl)Cl.CO | null | 1 | C=CCN=CC(C)CC=C>C(Cl)Cl.CO>C=CCNCC(C)CC=C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-641d6ec4383d4f94a02c686482e313a0 | C=CCNCC(C)CC=C.O=S(=O)(Cl)c1ccccn1>>C=CCC(C)CN(CC=C)S(=O)(=O)c1ccccn1 | C(C=C)NCC(CC=C)C.CN1CCOCC1.N1=C(C=CC=C1)S(=O)(=O)Cl>>C(C=C)N(S(=O)(=O)C1=NC=CC=C1)CC(CC=C)C | [CH2:1]=[CH:2][CH2:3][CH:4]([CH3:5])[CH2:6][NH:7][CH2:8][CH:9]=[CH2:10].Cl[S:11](=[O:12])(=[O:13])[c:14]1[cH:15][cH:16][cH:17][cH:18][n:19]1>>[CH2:1]=[CH:2][CH2:3][CH:4]([CH3:5])[CH2:6][N:7]([CH2:8][CH:9]=[CH2:10])[S:11](=[O:12])(=[O:13])[c:14]1[cH:15][cH:16][cH:17][cH:18][n:19]1 | C=CCNCC(C)CC=C.O=S(=O)(Cl)c1ccccn1 | C=CCC(C)CN(CC=C)S(=O)(=O)c1ccccn1 | null | null | C(Cl)Cl | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) secondary amine | f885e88ea942f3030166da4c7f20dfb8bf6f1e152c7507d56458611df7dc3120 | 971e620478d668662a3bf915b510f5704d42a595d6ca9c67de007bd5d7063a75 | c1ccncc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#7;a:6]:[c:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]=[C;D1;H2:13]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[C:11]-[C:12]=[C;D1;H2:13])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#7;a:6]:[c:7] | 60 | [{"value": 60.0, "product": "C(C=C)N(S(=O)(=O)C1=NC=CC=C1)CC(CC=C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.4, "product": "C(C=C)N(S(=O)(=O)C1=NC=CC=C1)CC(CC=C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Allyl-(2-methyl-pent-4-enyl)-amine (1.0 g, 7.2 mmol) and NMM (1.7 g, 17.2 mmol) were mixed in 30 ml CH2Cl2. 2-pyridinesulphonyl chloride (1.53 g, 8.6 mmol) was added slowly to the solution while it was cooled in an ice-water bath. After addition, the reaction mixture was stirred at RT overnight. The reaction mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | null | null | c1ccncc1 | HCl | C(Cl)Cl | null | 8 | C=CCNCC(C)CC=C.O=S(=O)(Cl)c1ccccn1>C(Cl)Cl>C=CCC(C)CN(CC=C)S(=O)(=O)c1ccccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3779a072da6845e4bf9e96143046af35 | C=CCC(C)CN(CC=C)S(=O)(=O)c1ccccn1>>CC1CC=CCN(S(=O)(=O)c2ccccn2)C1 | C(C=C)N(S(=O)(=O)C1=NC=CC=C1)CC(CC=C)C>>CC1CN(CC=CC1)S(=O)(=O)C1=NC=CC=C1 | C=C[CH2:6][N:7]([S:8](=[O:9])(=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][n:16]1)[CH2:17][CH:2]([CH3:1])[CH2:3][CH:4]=[CH2:5]>>[CH3:1][CH:2]1[CH2:3][CH:4]=[CH:5][CH2:6][N:7]([S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][n:16]2)[CH2:17]1 | C=CCC(C)CN(CC=C)S(=O)(=O)c1ccccn1 | CC1CC=CCN(S(=O)(=O)c2ccccn2)C1 | null | Cl[Ru](Cl)([P](C1CCCCC1)(C2CCCCC2)C3CCCCC3)([P](C4CCCCC4)(C5CCCCC5)C6CCCCC6)=CC7=CC=CC=C7 | C(Cl)Cl | C-C Coupling | OtherReaction | 1c1bcb324a99f1f7cdfad1cda20c60d4247a90d693ba0f29142115753e5db166 | 67a23c4de67c22dcd6bc1d4c033efdcf679af248440c3b10e6768679c5f73280 | O=S(=O)(c1ccccn1)N1CC=CCCC1 | C=C-[CH2;D2;+0:1]-[#7:2](-[#16:3])-[C:4].[C:5]-[C:6]=[CH2;D1;+0:7]>>[#16:3]-[#7:2](-[C:4])-[CH2;D2;+0:1]-[CH;D2;+0:7]=[C:6]-[C:5] | 83 | [{"value": 83.0, "product": "CC1CN(CC=CC1)S(=O)(=O)C1=NC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.9, "product": "CC1CN(CC=CC1)S(=O)(=O)C1=NC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Pyridine-2-sulfonic acid allyl-(2-methyl-pent-4enyl)-amide (1.2 g, 4.3 mmol) was diluted in CH2Cl2 (100 ml). After carefully degass by Ar, Grubbs catalyst (0.35 g, 0.43 mmol) was added under Ar protection. The mixture was then refluxed for 2 h before the reaction mixture was concentrated by rotary evaporation. The prod... | 10.6084/m9.figshare.5104873.v1 | null | Allyl.Allyl | null | null | C1=CC[NH]CCC1 | C1=CC[NH]CCC1.c1ccncc1 | Other | Cl[Ru](Cl)([P](C1CCCCC1)(C2CCCCC2)C3CCCCC3)([P](C4CCCCC4)(C5CCCCC5)C6CCCCC6)=CC7=CC=CC=C7.C(Cl)Cl | null | null | C=CCC(C)CN(CC=C)S(=O)(=O)c1ccccn1>Cl[Ru](Cl)([P](C1CCCCC1)(C2CCCCC2)C3CCCCC3)([P](C4CCCCC4)(C5CCCCC5)C6CCCCC6)=CC7=CC=CC=C7.C(Cl)Cl>CC1CC=CCN(S(=O)(=O)c2ccccn2)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a8fe934a6d7141508b4ff464e62c4dc0 | CC1CC=CCN(S(=O)(=O)c2ccccn2)C1>>CC1CC2OC2CN(S(=O)(=O)c2ccccn2)C1 | C1=CC(=CC(=C1)Cl)C(=O)OO.CC1CN(CC=CC1)S(=O)(=O)C1=NC=CC=C1.C(=O)(O)[O-].[Na+]>>CC1CN(CC2OC2C1)S(=O)(=O)C1=NC=CC=C1 | [CH3:1][CH:2]1[CH2:3][CH:4]=[CH:6][CH2:7][N:8]([S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][n:17]2)[CH2:18]1>>[CH3:1][CH:2]1[CH2:3][CH:4]2[O:5][CH:6]2[CH2:7][N:8]([S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][n:17]2)[CH2:18]1 | CC1CC=CCN(S(=O)(=O)c2ccccn2)C1 | CC1CC2OC2CN(S(=O)(=O)c2ccccn2)C1 | null | null | C(Cl)Cl | Oxidation | OtherReaction | 86f6c7b5d741dbfbac6f0a1f6d388f717e4c3dec0b97725f8e4d07c278db997e | 064ea107e05241c09a52d804a18982a555fc0def251e05abc9beed7ecad64b38 | O=S(=O)(c1ccccn1)N1CCCC2OC2C1 | [#16:1]-[#7:2]1-[C:3]-[C:4]-[C:5]-[CH;D2;+0:6]=[CH;D2;+0:7]-[C:8]-1>>[#16:1]-[#7:2]1-[C:3]-[C:4]-[C:5]-[CH;D3;+0:6]2-[#8:9]-[CH;D3;+0:7]-2-[C:8]-1 | null | [] | null | null | 4 | HOUR | To the solution of 3-methyl-1-(pyridine-2-sulfonyl)-2,3,4,7-tetrahydro-1H-azepine (1.3 g, 5.16 mmol) in CH2Cl2 (50 ml) was added NaHCO3 (1.3 g, 15.5 mmol) and then mCPBA (2.67 g, 15.5 mmol) in portions. Stirred at RT for 4 h before worked up by washing with 15% NaOH, saturated K2CO3 and brine. Dried over Na2SO4. The re... | 10.6084/m9.figshare.5104873.v1 | null | null | Ether | C1=CC[NH]CCC1 | C1C[NH]CC2OC2C1 | C1C[NH]CC2OC2C1.c1ccncc1 | Other | C(Cl)Cl | null | 4 | CC1CC=CCN(S(=O)(=O)c2ccccn2)C1>C(Cl)Cl>CC1CC2OC2CN(S(=O)(=O)c2ccccn2)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7aa9cdfe43284d549adfbad416cbc22d | CC1CC2OC2CN(S(=O)(=O)c2ccccn2)C1.[N-]=[N+]=[N-]>>CC1CCN(S(=O)(=O)c2ccccn2)CC(O)C1N=[N+]=[N-] | CC1CN(CC2OC2C1)S(=O)(=O)C1=NC=CC=C1.CO.[N-]=[N+]=[N-].[Na+].[NH4+].[Cl-]>>N(=[N+]=[N-])C1C(CN(CCC1C)S(=O)(=O)C1=NC=CC=C1)O | [CH3:1][CH:2]1[CH2:3][CH:4]2[CH:16]([CH2:15][N:5]([S:6](=[O:7])(=[O:8])[c:9]3[cH:10][cH:11][cH:12][cH:13][n:14]3)[CH2:18]1)[O:17]2.[N-:19]=[N+:20]=[N-:21]>>[CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([S:6](=[O:7])(=[O:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][n:14]2)[CH2:15][CH:16]([OH:17])[CH:18]1[N:19]=[N+:20]=[N-:21] | CC1CC2OC2CN(S(=O)(=O)c2ccccn2)C1.[N-]=[N+]=[N-] | CC1CCN(S(=O)(=O)c2ccccn2)CC(O)C1N=[N+]=[N-] | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 92f5311b0a29127004cb56f9e5d2a5fad4bce2b1de8be58ae0f5288b59854bc0 | 634c2d595269a81e6b5cfe8eae8905dc35e735e703140501d5c66d2255c93dda | O=S(=O)(c1ccccn1)N1CCCCCC1 | [#7;a:1]:[c:2]-[#16:3](=[O;D1;H0:4])(=[O;D1;H0:5])-[N;H0;D3;+0:6]1-[C:7]-[CH;D3;+0:8]2-[O;H0;D2;+0:9]-[CH;D3;+0:10]-2-[C:11]-[C:12](-[C;D1;H3:13])-[CH2;D2;+0:14]-1.[N-;H0;D1:15]=[#7;+:16]=[N;-;D1;H0:17]>>[#7;a:1]:[c:2]-[#16:3](=[O;D1;H0:4])(=[O;D1;H0:5])-[N;H0;D3;+0:6]1-[C:7]-[CH;D3;+0:8](-[OH;D1;+0:9])-[CH;D3;+0:14](-... | 64 | [{"value": 64.0, "product": "N(=[N+]=[N-])C1C(CN(CCC1C)S(=O)(=O)C1=NC=CC=C1)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-methyl-3-(pyridine-2-sulfonyl)-8-oxa-3-aza-bicyclo[5.1.0]octane (230 mg, 0.86 mmol) was dissolved in the mixture of 8 ml MeOH and 2 ml H2O. NaN3 (170 mg, 2.6 mmol) and NH4Cl (140 mg, 2.6 mmol) were added to the solution. The resulting mixture was refluxed overnight. After the removal of MeOH, the residue was diluted ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Tertiary amine | Azide.Secondary alcohol.Tertiary amine | C1C[NH]CC2OC2C1 | C1CCC[NH]CC1 | C1CCC[NH]CC1.c1ccncc1 | null | O | null | null | CC1CC2OC2CN(S(=O)(=O)c2ccccn2)C1.[N-]=[N+]=[N-]>O>CC1CCN(S(=O)(=O)c2ccccn2)CC(O)C1N=[N+]=[N-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-905cdf76f95e422faa92fe590460ae44 | CC1CC(N=[N+]=[N-])C(O)CN(S(=O)(=O)c2ccccn2)C1>>CC1CC(N)C(O)CN(S(=O)(=O)c2ccccn2)C1 | N(=[N+]=[N-])C1C(CN(CC(C1)C)S(=O)(=O)C1=NC=CC=C1)O.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3>>NC1C(CN(CC(C1)C)S(=O)(=O)C1=NC=CC=C1)O | [N-]=[N+]=[N:5][CH:4]1[CH2:3][CH:2]([CH3:1])[CH2:19][N:9]([S:10](=[O:11])(=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][n:18]2)[CH2:8][CH:6]1[OH:7]>>[CH3:1][CH:2]1[CH2:3][CH:4]([NH2:5])[CH:6]([OH:7])[CH2:8][N:9]([S:10](=[O:11])(=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][n:18]2)[CH2:19]1 | CC1CC(N=[N+]=[N-])C(O)CN(S(=O)(=O)c2ccccn2)C1 | CC1CC(N)C(O)CN(S(=O)(=O)c2ccccn2)C1 | null | null | O.C1CCOC1 | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | O=S(=O)(c1ccccn1)N1CCCCCC1 | [C:1]-[C:2](-[N;H0;D2;+0:3]=[N+]=[N-])-[C:4]>>[C:1]-[C:2](-[NH2;D1;+0:3])-[C:4] | 71 | [{"value": 71.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 45 | CELSIUS | null | null | 4-Azido-6-methyl-1-(pyridine-2-sulfonyl)-azepan-3-ol (0.33 g, 1.06 mmol) was dissolved in THF(50 ml) and H2O (0.2 ml). PPh3 (0.42 g, 1.59 mmol) was added to this solution. The reaction mixture was stirred at 45° C. over night. TLC showed no starting material left. THF was evaperated, azeotroped by toluene (2×100 ml). T... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | C1CCC[NH]CC1.c1ccncc1 | Other | O.C1CCOC1 | 45 | null | CC1CC(N=[N+]=[N-])C(O)CN(S(=O)(=O)c2ccccn2)C1>O.C1CCOC1>CC1CC(N)C(O)CN(S(=O)(=O)c2ccccn2)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-efc04689e9854710ae044a54779dfd87 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)O.CC1CC(N)C(O)CN(S(=O)(=O)c2ccccn2)C1>>CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)NC1CC(C)CN(S(=O)(=O)c2ccccn2)CC1O | CN1CCOCC1.N([C@@H](CC(C)C)C(=O)O)C(=O)OC(C)(C)C.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.F[P-](F)(F)(F)(F)F.Cl.NC1C(CN(CC(C1)C)S(=O)(=O)C1=NC=CC=C1)O>>C(C)(C)(C)OC(N[C@@H](CC(C)C)C(NC1C(CN(CC(C1)C)S(=O)(=O)C1=NC=CC=C1)O)=O)=O | O[C:14]([C@H:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:15].[NH2:16][CH:17]1[CH2:18][CH:19]([CH3:20])[CH2:21][N:22]([S:23](=[O:24])(=[O:25])[c:26]2[cH:27][cH:28][cH:29][cH:30][n:31]2)[CH2:32][CH:33]1[OH:34]>>[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH:6][C:7](=[O:8])[O:... | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)O.CC1CC(N)C(O)CN(S(=O)(=O)c2ccccn2)C1 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)NC1CC(C)CN(S(=O)(=O)c2ccccn2)CC1O | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=S(=O)(c1ccccn1)N1CCCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[C:13]-[C:14](-[NH2;D1;+0:15])-[C:16]>>[C:13]-[C:14](-[NH;D2;+0:15]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12... | 68 | [{"value": 68.0, "product": "C(C)(C)(C)OC(N[C@@H](CC(C)C)C(NC1C(CN(CC(C1)C)S(=O)(=O)C1=NC=CC=C1)O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.0, "product": "C(C)(C)(C)OC(N[C@@H](CC(C)C)C(NC1C(CN(CC(C1)C)S(=O)(=O)C1=NC=CC=C1)O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 4-Amino-6-methyl-1-(pyridine-2-sulfonyl)-azepan-3-ol HCl salt (0.21 g, 0.59 mmol) was dissolved in 5 ml DMF. To this solution, was added Boc-Leu-OH (0.22 g, 0.88 mmol)and HBTU (0.34 g, 0.90 mmol) and then NMM (0.24 g, 2.4 mmol). The mixture was stirred at RT overnight. DMF was removed under high vacuum. The residue was... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CCC[NH]CC1.c1ccncc1 | HO- | CN(C)C=O | null | 8 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)O.CC1CC(N)C(O)CN(S(=O)(=O)c2ccccn2)C1>CN(C)C=O>CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)NC1CC(C)CN(S(=O)(=O)c2ccccn2)CC1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3648588902864b24ab08bf9b5bb518bc | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)NC1CC(C)CN(S(=O)(=O)c2ccccn2)CC1O.COc1ccc2oc(C(=O)O)cc2c1>>COc1ccc2oc(C(=O)N[C@@H](CC(C)C)C(=O)NC3CC(C)CN(S(=O)(=O)c4ccccn4)CC3O)cc2c1 | COC=1C=CC2=C(C=C(O2)C(=O)O)C1.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.F[P-](F)(F)(F)(F)F.CN1CCOCC1.C(C)(C)(C)OC(N[C@@H](CC(C)C)C(NC1C(CN(CC(C1)C)S(=O)(=O)C1=NC=CC=C1)O)=O)=O.Cl.O1CCOCC1.Cl>>OC1CN(CC(CC1NC(=O)[C@H](CC(C)C)NC(=O)C=1OC2=C(C1)C=C(C=C2)OC)C)S(=O)(=O)C2=NC=CC=C2 | CC(C)(C)OC(=O)[NH:11][C@@H:12]([CH2:13][CH:14]([CH3:15])[CH3:16])[C:17](=[O:18])[NH:19][CH:20]1[CH2:21][CH:22]([CH3:23])[CH2:24][N:25]([S:26](=[O:27])(=[O:28])[c:29]2[cH:30][cH:31][cH:32][cH:33][n:34]2)[CH2:35][CH:36]1[OH:37].O[C:9]([c:8]1[o:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:40][c:39]2[cH:38]1)=[O:10]>>[CH3:1]... | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)NC1CC(C)CN(S(=O)(=O)c2ccccn2)CC1O.COc1ccc2oc(C(=O)O)cc2c1 | COc1ccc2oc(C(=O)N[C@@H](CC(C)C)C(=O)NC3CC(C)CN(S(=O)(=O)c4ccccn4)CC3O)cc2c1 | null | null | null | Acylation | OtherReaction | 510680c124a6407ad270065ce067b02da7b27d9b855c374df163b757a8749f7f | 7457c724cd0cfe2d26ffa0aef6c4027e2d3dc4704bac959e83de51cafcce5bb3 | O=C(CNC(=O)c1cc2ccccc2o1)NC1CCCN(S(=O)(=O)c2ccccn2)CC1 | 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].O-[C;H0;D3;+0:8](=[O;D1;H0:9])-[c:10](:[c:11]):[#8;a:12]:[c:13]>>[C:3]-[C:2](-[NH;D2;+0:1]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[c:10](:[c:11]):[#8;a:12]:[c:13])-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7] | 69 | [{"value": 69.0, "product": "OC1CN(CC(CC1NC(=O)[C@H](CC(C)C)NC(=O)C=1OC2=C(C1)C=C(C=C2)OC)C)S(=O)(=O)C2=NC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.6, "product": "OC1CN(CC(CC1NC(=O)[C@H](CC(C)C)NC(=O)C=1OC2=C(C1)C=C(C=C2)OC)C)S(=O)(=O)C2=NC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_d... | null | null | 8 | HOUR | To {(S)-1-[3-hydroxy-6-methyl-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-3-methyl-butyl}-carbamic acid tert-butyl ester (0.13 g, 0.28 mmol) was added HCl/dioxane (4M, 2.8 ml, 11.2 mmol). The mixture was stirred at RT for 2 h before solvents and excess amount of HCl was removed on rotavapor. The result white solid wa... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Boc | Secondary amide | null | null | c1ccc2occc2c1.C1CCC[NH]CC1.c1ccncc1 | HO- | null | null | 8 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)NC1CC(C)CN(S(=O)(=O)c2ccccn2)CC1O.COc1ccc2oc(C(=O)O)cc2c1>>COc1ccc2oc(C(=O)N[C@@H](CC(C)C)C(=O)NC3CC(C)CN(S(=O)(=O)c4ccccn4)CC3O)cc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-30ea4751d59044d2b900a87fca94ded2 | COc1ccc2oc(C(=O)N[C@@H](CC(C)C)C(=O)NC3CC(C)CN(S(=O)(=O)c4ccccn4)CC3O)cc2c1>>COc1ccc2oc(C(=O)N[C@@H](CC(C)C)C(=O)N[C@H]3C[C@H](C)CN(S(=O)(=O)c4ccccn4)CC3=O)cc2c1 | OC1CN(CC(CC1NC(=O)[C@H](CC(C)C)NC(=O)C=1OC2=C(C1)C=C(C=C2)OC)C)S(=O)(=O)C2=NC=CC=C2.CC(=O)OI1(C=2C=CC=CC2C(=O)O1)(OC(=O)C)OC(=O)C>>CC(C[C@@H](C(N[C@@H]1C(CN(C[C@H](C1)C)S(=O)(=O)C1=NC=CC=C1)=O)=O)NC(=O)C=1OC2=C(C1)C=C(C=C2)OC)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[o:7][c:8]([C:9](=[O:10])[NH:11][C@@H:12]([CH2:13][CH:14]([CH3:15])[CH3:16])[C:17](=[O:18])[NH:19][CH:20]3[CH2:21][CH:22]([CH3:23])[CH2:24][N:25]([S:26](=[O:27])(=[O:28])[c:29]4[cH:30][cH:31][cH:32][cH:33][n:34]4)[CH2:35][CH:36]3[OH:37])[cH:38][c:39]2[cH:40]1>>[CH3:1][O:2][c:3]1[cH:4... | COc1ccc2oc(C(=O)N[C@@H](CC(C)C)C(=O)NC3CC(C)CN(S(=O)(=O)c4ccccn4)CC3O)cc2c1 | COc1ccc2oc(C(=O)N[C@@H](CC(C)C)C(=O)N[C@H]3C[C@H](C)CN(S(=O)(=O)c4ccccn4)CC3=O)cc2c1 | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 14b488e4129d7de2d07ca6b39e641a5c8222ffe6452ab415aeabbdbcc777a2ba | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C(CNC(=O)c1cc2ccccc2o1)N[C@H]1CCCN(S(=O)(=O)c2ccccn2)CC1=O | [#16:1]-[#7:2]1-[C:3]-[C:4]-[C:5]-[CH;D3;+0:6](-[#7:7]-[C:8](-[C:9])=[O;D1;H0:10])-[CH;D3;+0:11](-[OH;D1;+0:12])-[C:13]-1>>[#16:1]-[#7:2]1-[C:3]-[C:4]-[C:5]-[C@H;D3;+0:6](-[#7:7]-[C:8](-[C:9])=[O;D1;H0:10])-[C;H0;D3;+0:11](=[O;H0;D1;+0:12])-[C:13]-1 | 83 | [{"value": 82.0, "product": "CC(C[C@@H](C(N[C@@H]1C(CN(C[C@H](C1)C)S(=O)(=O)C1=NC=CC=C1)=O)=O)NC(=O)C=1OC2=C(C1)C=C(C=C2)OC)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.0, "product": "CC(C[C@@H](C(N[C@@H]1C(CN(C[C@H](C1)C)S(=O)(=O)C1=NC=CC=C1)=O)=O)NC(=O)C=1OC2=C(C1)C=C(C=C2)OC)C", "details": "CALC... | null | null | null | null | To a solution of 5-methoxy-benzofuran-2-carboxylic acid {(S)-1-[3-hydroxy-6-methyl-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-3-methyl-butyl}-amide (110 mg, 0.19 mmol) in 5 ml CH2Cl2, was added Dess-Martin reagent (122 mg, 0.29 mmol) at RT. The solution was stirred for 2 h when 50 ml CH2Cl2 was added and then washed... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | C1CCC[NH]CC1 | C1CCC[NH]CC1 | c1ccc2occc2c1.C1CCC[NH]CC1.c1ccncc1 | null | C(Cl)Cl | null | null | COc1ccc2oc(C(=O)N[C@@H](CC(C)C)C(=O)NC3CC(C)CN(S(=O)(=O)c4ccccn4)CC3O)cc2c1>C(Cl)Cl>COc1ccc2oc(C(=O)N[C@@H](CC(C)C)C(=O)N[C@H]3C[C@H](C)CN(S(=O)(=O)c4ccccn4)CC3=O)cc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-09f4020875874426a74d475a4e4e5dbd | C=CCCC(C)=O.C=CCN.Cc1ccc(S(=O)(=O)O)cc1>>C=CCCC(C)=NCC=C.C=CCCC(C)NCC=C | CC(CCC=C)=O.C(C=C)N.C1(=CC=C(C=C1)S(=O)(=O)O)C>>C(C=C)NC(CCC=C)C.C(C=C)N=C(CCC=C)C | O=[C:15]([CH2:14][CH2:13][CH:12]=[CH2:11])[CH3:16].[NH2:7][CH2:8][CH:9]=[CH2:10].O=S(=O)(O)[c:20]1[cH:1][cH:4][c:5]([CH3:6])[cH:18][cH:19]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][C:5]([CH3:6])=[N:7][CH2:8][CH:9]=[CH2:10].[CH2:11]=[CH:12][CH2:13][CH2:14][CH:15]([CH3:16])[NH:17][CH2:18][CH:19]=[CH2:20] | C=CCCC(C)=O.C=CCN.Cc1ccc(S(=O)(=O)O)cc1 | C=CCCC(C)=NCC=C.C=CCCC(C)NCC=C | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | b23820ed29f4dfb19ab6d0e574ebf602cf0a16c57595452513bf1f8eecc61df5 | ec6dbfbe6f9d83344fbafee96b7336b120256a168cf0de240708ea47506514cb | null | O-S(=O)(=O)-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[cH;D2;+0:3]:[c;H0;D3;+0:4](-[C;D1;H3:5]):[cH;D2;+0:6]:[cH;D2;+0:7]:1.O=[C;H0;D3;+0:8](-[C;D1;H3:9])-[C:10]-[C:11]-[C:12]=[C;D1;H2:13].[C;D1;H2:14]=[C:15]-[C:16]-[NH2;D1;+0:17]>>[C;D1;H2:13]=[C:12]-[C:11]-[C:10]-[CH;D3;+0:8](-[C;D1;H3:9])-[#7:18]-[CH2;D2;+0:3]-[CH;D2;+0:2]=[CH2;... | null | [] | null | null | 8 | HOUR | Hex-5-en-2-one (9.8 g, 11.6 ml, 100 mmol) was added to a stirred solution of allylamine (8.55 mmol, 11.25 ml, 150 mmol), 4 Angstrom molecular sieves (52 g), and p-toluene sulfonic acid (10 mg) in CH2Cl2 (200 ml) and was stirred overnight. The reaction mixture was concentrated in vacuo by rotary evaporation and was used... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Ketone.Primary amine | Substituted imine.Secondary amine.Allyl.Allyl | c1ccccc1 | null | null | Other | C(Cl)Cl | null | 8 | C=CCCC(C)=O.C=CCN.Cc1ccc(S(=O)(=O)O)cc1>C(Cl)Cl>C=CCCC(C)=NCC=C.C=CCCC(C)NCC=C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-95156f87f4f64dd0b65192139a02a10d | C=CCCC(C)=NCC=C>>C=CCCC(C)NCC=C | [BH4-].[Na+].C(C=C)N=C(CCC=C)C>>C(C=C)NC(CCC=C)C | [CH2:1]=[CH:2][CH2:3][CH2:4][C:5]([CH3:6])=[N:7][CH2:8][CH:9]=[CH2:10]>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH:5]([CH3:6])[NH:7][CH2:8][CH:9]=[CH2:10] | C=CCCC(C)=NCC=C | C=CCCC(C)NCC=C | null | null | CO | Reduction | OtherReaction | d4a3c3af6b6e3a46274c741e9feddcd7af52a8fba8716af75123ec94a3d0151d | 469efbca661320a0d72c32f19625ec46edbc3ad7686cf46fdd0591eb136a8d7e | null | [C;D1;H2:1]=[C:2]-[C:3]-[N;H0;D2;+0:4]=[C;H0;D3;+0:5](-[C;D1;H3:6])-[C:7]-[C:8]-[C:9]=[C;D1;H2:10]>>[C;D1;H2:1]=[C:2]-[C:3]-[NH;D2;+0:4]-[CH;D3;+0:5](-[C;D1;H3:6])-[C:7]-[C:8]-[C:9]=[C;D1;H2:10] | null | [] | null | null | 30 | MINUTE | Sodium borohydride (2.7 g, 71 mmol) was added portionwise to a stirred solution of allyl-(1-methyl-pent-4-enylidene)-amine (6.5 g, 47 mmol) in MeOH (100 ml) at 0 C. The reaction mixture was stirred for 30 minutes, then warmed to RT. Approximately 90 ml of MeOH was removed from the reaction mixture by rotary evaporation... | 10.6084/m9.figshare.5104873.v1 | null | Substituted imine | Secondary amine | null | null | null | null | CO | null | 0.5 | C=CCCC(C)=NCC=C>CO>C=CCCC(C)NCC=C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-13dcccafe5e44af2930e2ec876392e13 | C=CCCC(C)NCC=C.O=C(Cl)OCc1ccccc1>>C=CCCC(C)N(CC=C)C(=O)OCc1ccccc1 | C(=O)(OCC1=CC=CC=C1)Cl.C(C=C)NC(CCC=C)C.C(C)N(CC)CC>>C(C1=CC=CC=C1)OC(N(C(CCC=C)C)CC=C)=O | [CH2:1]=[CH:2][CH2:3][CH2:4][CH:5]([CH3:6])[NH:7][CH2:8][CH:9]=[CH2:10].Cl[C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH:5]([CH3:6])[N:7]([CH2:8][CH:9]=[CH2:10])[C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | C=CCCC(C)NCC=C.O=C(Cl)OCc1ccccc1 | C=CCCC(C)N(CC=C)C(=O)OCc1ccccc1 | null | null | C(Cl)Cl | Protection | N-alkylation of secondary amines with alkyl halides | 496a200c7c2fc7c000296e03cda40efb8e258ccaeb02fa999285bf74ddc49346 | d86dc1e6d0e089b3444b62ddfcf4c4822bdac4b60e628553036562518c29adcd | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]-[C:6](-[C;D1;H3:7])-[NH;D2;+0:8]-[C:9]-[C:10]=[C;D1;H2:11]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:8](-[C:9]-[C:10]=[C;D1;H2:11])-[C:6](-[C:5])-[C;D1;H3:7] | 65.1 | [{"value": 65.0, "product": "C(C1=CC=CC=C1)OC(N(C(CCC=C)C)CC=C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.1, "product": "C(C1=CC=CC=C1)OC(N(C(CCC=C)C)CC=C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Carbobenzyloxy chloride (9.56 g, 8 ml) was added dropwise to a stirred solution of allyl-(1-methyl-pent-4-enyl)-amine (7 g, 50 mmol), triethylamine (5.5 g, 8.0 ml, 57.5 mmol) in CH2Cl2 (100 ml) at 0 C. The reaction mixture was warmed to RT, then was stirred for 2 h. The reaction mixture was diluted with CH2Cl2 (100 ml)... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amine | Carbamic ester | null | null | c1ccccc1 | HCl | C(Cl)Cl | null | 2 | C=CCCC(C)NCC=C.O=C(Cl)OCc1ccccc1>C(Cl)Cl>C=CCCC(C)N(CC=C)C(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-753dc12b5c0e4a34afb5a60fef2f8527 | C=CCCC(C)N(CC=C)C(=O)OCc1ccccc1>>CC1CCC=CCN1C(=O)OCc1ccccc1 | C(C1=CC=CC=C1)OC(N(C(CCC=C)C)CC=C)=O>>C(C1=CC=CC=C1)OC(=O)N1C(CCC=CC1)C | C=[CH:5][CH2:4][CH2:3][CH:2]([CH3:1])[N:8]([CH2:7][CH:6]=C)[C:9](=[O:10])[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH:5]=[CH:6][CH2:7][N:8]1[C:9](=[O:10])[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | C=CCCC(C)N(CC=C)C(=O)OCc1ccccc1 | CC1CCC=CCN1C(=O)OCc1ccccc1 | null | C=CC1=CC=CC=C1.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Ru]Cl.C=CC1=CC=CC=C1.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Ru]Cl | C(Cl)Cl | C-C Coupling | OtherReaction | 1c1bcb324a99f1f7cdfad1cda20c60d4247a90d693ba0f29142115753e5db166 | 67a23c4de67c22dcd6bc1d4c033efdcf679af248440c3b10e6768679c5f73280 | O=C(OCc1ccccc1)N1CC=CCCC1 | C=[CH;D2;+0:1]-[C:2]-[#7:3]-[C:4]=[O;D1;H0:5].C=[CH;D2;+0:6]-[C:7]-[C:8]>>[C:8]-[C:7]-[CH;D2;+0:6]=[CH;D2;+0:1]-[C:2]-[#7:3]-[C:4]=[O;D1;H0:5] | 89 | [{"value": 89.0, "product": "C(C1=CC=CC=C1)OC(=O)N1C(CCC=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.0, "product": "C(C1=CC=CC=C1)OC(=O)N1C(CCC=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Allyl-(1-methyl-pent-4-enyl)-carbamic acid benzyl ester (1.036 g, 3.8 mmol) was dissolved in CH2Cl2 (10 ml) and a stream of argon gas was bubbled into the reaction mixture for 10 minutes. Then bis(tricyclohexylphosphine)benzylidine ruthenium(IV) dichloride (Strem Chemicals, Grubbs' catalyst, 22 mg, 0.027 mmol) was adde... | 10.6084/m9.figshare.5104873.v1 | null | Allyl.Allyl | null | null | C1=CC[NH]CCC1 | C1=CC[NH]CCC1.c1ccccc1 | Other | C=CC1=CC=CC=C1.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Ru]Cl.C=CC1=CC=CC=C1.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Ru]Cl.C(Cl)Cl | null | null | C=CCCC(C)N(CC=C)C(=O)OCc1ccccc1>C=CC1=CC=CC=C1.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Ru]Cl.C=CC1=CC=CC=C1.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Ru]Cl.C(Cl)Cl>CC1CCC=CCN1C(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ddaf0bbb2bfd4fa883ae90f4cfbeb0f3 | CC1CCC2OC2CN1C(=O)OCc1ccccc1.[N-]=[N+]=[N-]>>CC1CCC(N=[N+]=[N-])C(O)CN1C(=O)OCc1ccccc1 | [N-]=[N+]=[N-].[Na+].C(C1=CC=CC=C1)OC(=O)N1CC2OC2CCC1C.[Cl-].[NH4+]>>C(C1=CC=CC=C1)OC(=O)N1C(CCC(C(C1)O)N=[N+]=[N-])C | [CH3:1][CH:2]1[CH2:3][CH2:4][CH:5]2[CH:9]([O:10]2)[CH2:11][N:12]1[C:13](=[O:14])[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[N-:6]=[N+:7]=[N-:8]>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH:5]([N:6]=[N+:7]=[N-:8])[CH:9]([OH:10])[CH2:11][N:12]1[C:13](=[O:14])[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | CC1CCC2OC2CN1C(=O)OCc1ccccc1.[N-]=[N+]=[N-] | CC1CCC(N=[N+]=[N-])C(O)CN1C(=O)OCc1ccccc1 | null | null | O.CO | Heteroatom Alkylation and Arylation | OtherReaction | e146978056990f665c16db7baca0807e76628e76e5b06bd667731dfa3c7d52c8 | 0de57b50a6157507e9baab9ed62d7e11e29441a6de9ee7172f74a5b142f47048 | O=C(OCc1ccccc1)N1CCCCCC1 | [#7:1]-[C:2]-[C:3]1-[O;H0;D2;+0:4]-[CH;D3;+0:5]-1-[C:6]-[C:7].[N-;H0;D1:8]=[#7;+:9]=[N;-;D1;H0:10]>>[#7:1]-[C:2]-[C:3](-[OH;D1;+0:4])-[CH;D3;+0:5](-[N;H0;D2;+0:8]=[#7;+:9]=[N;-;D1;H0:10])-[C:6]-[C:7] | 80.1 | [{"value": 80.0, "product": "C(C1=CC=CC=C1)OC(=O)N1C(CCC(C(C1)O)N=[N+]=[N-])C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.1, "product": "C(C1=CC=CC=C1)OC(=O)N1C(CCC(C(C1)O)N=[N+]=[N-])C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Sodium azide (0.56 g, 8.62 mmol) was added to a solution of racemic (1S,4R,7R)-4-methyl-8-oxa-3-aza-bicyclo[5.1.0]octane-3-carboxylic acid benzyl ester (0.75 g, 2.87 mmol) and ammonium chloride (0.46 g, 8.62 mmol) in MeOH (5 ml) and H2O (0.5 ml), then was refluxed for 6 h. The reaction mixture was concentrated in vacuo... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Azide.Secondary alcohol | C1C[NH]CC2OC2C1 | C1CCC[NH]CC1 | C1CCC[NH]CC1.c1ccccc1 | null | O.CO | null | null | CC1CCC2OC2CN1C(=O)OCc1ccccc1.[N-]=[N+]=[N-]>O.CO>CC1CCC(N=[N+]=[N-])C(O)CN1C(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-43e157a4e81d43778d62ce7ac6bb9e65 | CC1CCC(N=[N+]=[N-])C(O)CN1C(=O)OCc1ccccc1>>CC1CCC(N)C(O)CN1C(=O)OCc1ccccc1 | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C1=CC=CC=C1)OC(=O)N1C(CCC(C(C1)O)N=[N+]=[N-])C>>C(C1=CC=CC=C1)OC(=O)N1C(CCC(C(C1)O)N)C | [N-]=[N+]=[N:6][CH:5]1[CH2:4][CH2:3][CH:2]([CH3:1])[N:10]([C:11](=[O:12])[O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:9][CH:7]1[OH:8]>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH:5]([NH2:6])[CH:7]([OH:8])[CH2:9][N:10]1[C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | CC1CCC(N=[N+]=[N-])C(O)CN1C(=O)OCc1ccccc1 | CC1CCC(N)C(O)CN1C(=O)OCc1ccccc1 | null | null | O.C1(=CC=CC=C1)C.C1CCOC1 | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | O=C(OCc1ccccc1)N1CCCCCC1 | [C:1]-[C:2](-[N;H0;D2;+0:3]=[N+]=[N-])-[C:4]>>[C:1]-[C:2](-[NH2;D1;+0:3])-[C:4] | null | [] | 45 | CELSIUS | null | null | Triphenylphosphine (1.94 g, 7.4 mmol) was added to a solution of racemic (2R,5S,6S)-5-azido-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl ester (1.5 g, 4.93 mmol) in THF (185 ml) and H2O (0.7 ml), then was heated to 45 degrees C. overnight. The reaction mixture was then diluted with toluene (100 ml×2) and was aze... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | C1CCC[NH]CC1.c1ccccc1 | Other | O.C1(=CC=CC=C1)C.C1CCOC1 | 45 | null | CC1CCC(N=[N+]=[N-])C(O)CN1C(=O)OCc1ccccc1>O.C1(=CC=CC=C1)C.C1CCOC1>CC1CCC(N)C(O)CN1C(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dfab0feb9b0744239c1e5f37d3b19072 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@@H]1CC[C@H](C)NC[C@H]1O.CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NC[C@@H]1O.CN1CCOCC1.O=S(=O)(Cl)c1ccccn1>>CC(C)C[C@H](NC(=O)c1cc2ccccc2o1)C(=O)N[C@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)CC1=O | N1=C(C=CC=C1)S(=O)(=O)Cl.C(C)(C)(C)OC(N[C@@H](CC(C)C)C(N[C@@H]1[C@H](CN[C@@H](CC1)C)O)=O)=O.C(C)(C)(C)OC(N[C@@H](CC(C)C)C(N[C@H]1[C@@H](CN[C@H](CC1)C)O)=O)=O.CN1CCOCC1>>CC(C[C@@H](C(N[C@@H]1C(CN([C@@H](CC1)C)S(=O)(=O)C1=NC=CC=C1)=O)=O)NC(=O)C=1OC2=C(C1)C=CC=C2)C | C[C@H]1CC[C@@H:10](NC(=O)[C@H](C[CH:13](C)[CH3:12])NC(=O)OC(C)(C)C)[C@H:9]([OH:17])CN1.CC(C)(C)O[C:7]([NH:6][C@@H:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[C:18](=[O:19])[NH:20][C@H:21]1[CH2:22][CH2:23][C@@H:24]([CH3:25])[NH:26][CH2:36][C@@H:37]1[OH:38])=[O:8].CN1[CH2:14][CH2:15]O[CH2:11][CH2:16]1.Cl[S:27](=[O:28])(=[O:29])[c:... | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@@H]1CC[C@H](C)NC[C@H]1O.CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NC[C@@H]1O.CN1CCOCC1.O=S(=O)(Cl)c1ccccn1 | CC(C)C[C@H](NC(=O)c1cc2ccccc2o1)C(=O)N[C@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)CC1=O | null | null | C(Cl)Cl.CCOC(=O)C | Aromatic Heterocycle Formation | OtherReaction | 837a321e8bfb48d7ad18be728e873cdd16a5b9063affaa58a39693b3d0cd2207 | 96ea0316a4138a31db81b211e827b9fd42aedce4d85e020b221b32441cb9e5e5 | O=C(CNC(=O)c1cc2ccccc2o1)N[C@H]1CCCN(S(=O)(=O)c2ccccn2)CC1=O | null | 64 | [{"value": 64.0, "product": "CC(C[C@@H](C(N[C@@H]1C(CN([C@@H](CC1)C)S(=O)(=O)C1=NC=CC=C1)=O)=O)NC(=O)C=1OC2=C(C1)C=CC=C2)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 2-Pyridine sulfonyl chloride (0.6 g, 3.4 mmol) was added to a solution of [(S)-1-((3S,4S,7R)-3-Hydroxy-7-methyl-azepan-4-ylcarbamoyl)-3-methyl-butyl]-carbamic acid tert-butyl ester and [(S)-1-((3R,4R,7S)-3-hydroxy-7-methyl-azepan-4-ylcarbamoyl)-3-methyl-butyl]-carbamic acid tert-butyl ester (1.0, g, 2.8 mmol), N-methyl... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ether.Ether.Ether.Secondary amide.Secondary alcohol.Secondary alcohol.Secondary amine.Secondary amine.Tertiary amine.Sulfonyl halide.Boc.Boc | Ketone.Secondary amide.Tertiary amine | C1CCCNCC1.C1CCCNCC1.C1COCCN1 | c1ccc2occc2c1.C1CCC[NH]CC1 | c1ccc2occc2c1.C1CCC[NH]CC1.c1ccncc1 | HCl | C(Cl)Cl.CCOC(=O)C | null | 8 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@@H]1CC[C@H](C)NC[C@H]1O.CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NC[C@@H]1O.CN1CCOCC1.O=S(=O)(Cl)c1ccccn1>C(Cl)Cl.CCOC(=O)C>CC(C)C[C@H](NC(=O)c1cc2ccccc2o1)C(=O)N[C@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)CC1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c93dfde8f46a4a40af970ee76500053a | CC(C)C[C@H](NC(=O)c1cc2ccccc2o1)C(=O)N[C@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)C[C@@H]1O>>CC(C)C[C@H](NC(=O)c1cc2ccccc2o1)C(=O)N[C@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)CC1=O | CC(=O)OI1(C=2C=CC=CC2C(=O)O1)(OC(=O)C)OC(=O)C.O[C@H]1CN([C@@H](CC[C@@H]1NC(=O)[C@H](CC(C)C)NC(=O)C=1OC2=C(C1)C=CC=C2)C)S(=O)(=O)C2=NC=CC=C2.O[C@@H]1CN([C@H](CC[C@H]1NC(=O)[C@H](CC(C)C)NC(=O)C=1OC2=C(C1)C=CC=C2)C)S(=O)(=O)C2=NC=CC=C2>>CC(C[C@@H](C(N[C@@H]1C(CN([C@@H](CC1)C)S(=O)(=O)C1=NC=CC=C1)=O)=O)NC(=O)C=1OC2=C(C1)C=... | [CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH:6][C:7](=[O:8])[c:9]1[cH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[o:17]1)[C:18](=[O:19])[NH:20][C@H:21]1[CH2:22][CH2:23][C@@H:24]([CH3:25])[N:26]([S:27](=[O:28])(=[O:29])[c:30]2[cH:31][cH:32][cH:33][cH:34][n:35]2)[CH2:36][C@@H:37]1[OH:38]>>[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:... | CC(C)C[C@H](NC(=O)c1cc2ccccc2o1)C(=O)N[C@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)C[C@@H]1O | CC(C)C[C@H](NC(=O)c1cc2ccccc2o1)C(=O)N[C@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)CC1=O | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 14b488e4129d7de2d07ca6b39e641a5c8222ffe6452ab415aeabbdbcc777a2ba | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C(CNC(=O)c1cc2ccccc2o1)N[C@H]1CCCN(S(=O)(=O)c2ccccn2)CC1=O | [#16:1]-[#7:2](-[C:3])-[C:4]-[C@H;D3;+0:5](-[OH;D1;+0:6])-[C:7](-[#7:8]-[C:9]=[O;D1;H0:10])-[C:11]>>[#16:1]-[#7:2](-[C:3])-[C:4]-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-[C:7](-[#7:8]-[C:9]=[O;D1;H0:10])-[C:11] | null | [] | null | null | 45 | MINUTE | Dess-Martin periodinane (1.0 g, 2.36 mmol) was added to a solution of benzofuran-2-carboxylic acid {(S)-1-[(3S,4S,7R)-3-hydroxy-7-methyl-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-3-methyl-butyl}-amide and benzofuran-2-carboxylic acid {(S)-1-[(3R,4R,7S)-3-hydroxy-7-methyl-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | C1CCC[NH]CC1 | C1CCC[NH]CC1 | c1ccc2occc2c1.C1CCC[NH]CC1.c1ccncc1 | null | C(Cl)Cl | null | 0.75 | CC(C)C[C@H](NC(=O)c1cc2ccccc2o1)C(=O)N[C@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)C[C@@H]1O>C(Cl)Cl>CC(C)C[C@H](NC(=O)c1cc2ccccc2o1)C(=O)N[C@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)CC1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1f57a8ad80464d84a79af0bd3a4c8602 | C[C@H](CO)NC(=O)OCc1ccccc1.II>>C[C@H](CI)NC(=O)OCc1ccccc1 | C(C1=CC=CC=C1)OC(N[C@@H](CO)C)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N1C=NC=C1.II>>C(C1=CC=CC=C1)OC(N[C@@H](CI)C)=O | O[CH2:3][C@@H:2]([CH3:1])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.I[I:4]>>[CH3:1][C@H:2]([CH2:3][I:4])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | C[C@H](CO)NC(=O)OCc1ccccc1.II | C[C@H](CI)NC(=O)OCc1ccccc1 | null | null | O.C(Cl)Cl | Functional Group Interconversion | OtherReaction | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccccc1 | I-[I;H0;D1;+0:1].O-[CH2;D2;+0:2]-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7]>>[C;D1;H3:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[CH2;D2;+0:2]-[I;H0;D1;+0:1] | null | [] | 0 | CELSIUS | 3 | HOUR | Triphenylphospine (24 g, 91.8 mmol) was added to a solution of imidazole (12.5 g, 184 mmol) in CH2Cl2 (231 ml), then was cooled to 0 degrees C. Iodine (23.3 g, 91.8 mmol) was added to the suspension. The reaction mixture turned yellow, then faintly brown. After 5 minutes ((R)-2-hydroxy-1-methyl-ethyl)-carbamic acid ben... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccccc1 | HI | O.C(Cl)Cl | 0 | 3 | C[C@H](CO)NC(=O)OCc1ccccc1.II>O.C(Cl)Cl>C[C@H](CI)NC(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6ac102e4fc144e51b096767a4361be7a | C=C[CH2][Mg][Cl].C[C@H](CI)NC(=O)OCc1ccccc1>>C=CCC[C@@H](C)NC(=O)OCc1ccccc1 | C(C=C)[Mg]Cl.C(C1=CC=CC=C1)OC(N[C@@H](CI)C)=O>>C(C1=CC=CC=C1)OC(N[C@@H](CCC=C)C)=O | [Cl][Mg][CH2:3][CH:2]=[CH2:1].I[CH2:4][C@@H:5]([CH3:6])[NH:7][C:8](=[O:9])[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][C@@H:5]([CH3:6])[NH:7][C:8](=[O:9])[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | C=C[CH2][Mg][Cl].C[C@H](CI)NC(=O)OCc1ccccc1 | C=CCC[C@@H](C)NC(=O)OCc1ccccc1 | null | CSC.[Cu]Br | C1CCOC1 | C-C Coupling | OtherReaction | 95388f86cfea993e1d805de665d94c100ee3193d1978ecc8dd5e389bef693379 | d05251cf430cdb8f7fa37cdc312f93d4b47af4d8ed879f979cecc41cba4e1db9 | c1ccccc1 | I-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])-[#7:4]-[C:5]=[O;D1;H0:6].[C;D1;H2:7]=[C:8]-[CH2;D2;+0:9]-[Mg]-[Cl]>>[C;D1;H2:7]=[C:8]-[CH2;D2;+0:9]-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])-[#7:4]-[C:5]=[O;D1;H0:6] | null | [] | -78 | CELSIUS | 30 | MINUTE | Copper (I) bromide-dimethyl sulfide (1.93 g, 9.4 mmol) was dissolved in distilled THF (24 ml), then was cooled to −78 degrees C. A solution of allyl magnesium chloride (9.4 ml, 2M in THF, Aldrich) was added dropwise, then the solution was stirred for 30 minutes. ((R)-2-Iodo-1-methyl-ethyl)-carbamic acid benzyl ester (1... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Primary halide.Allyl | Allyl | null | null | c1ccccc1 | I-.Mg | CSC.[Cu]Br.C1CCOC1 | -78 | 0.5 | C=C[CH2][Mg][Cl].C[C@H](CI)NC(=O)OCc1ccccc1>CSC.[Cu]Br.C1CCOC1>C=CCC[C@@H](C)NC(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bfdbd19c33c24709892abbe9d2cd16ca | C=CCBr.C=CCC[C@@H](C)NC(=O)OCc1ccccc1>>C=CCC[C@@H](C)N(CC=C)C(=O)OCc1ccccc1 | Cl.[H-].[Na+].C(C1=CC=CC=C1)OC(N[C@@H](CCC=C)C)=O.C(C=C)Br>>C(C1=CC=CC=C1)OC(N([C@@H](CCC=C)C)CC=C)=O | Br[CH2:8][CH:9]=[CH2:10].[CH2:1]=[CH:2][CH2:3][CH2:4][C@@H:5]([CH3:6])[NH:7][C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][C@@H:5]([CH3:6])[N:7]([CH2:8][CH:9]=[CH2:10])[C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | C=CCBr.C=CCC[C@@H](C)NC(=O)OCc1ccccc1 | C=CCC[C@@H](C)N(CC=C)C(=O)OCc1ccccc1 | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 9f7a278cd5a191722d3eecc8371d7231da3fad2a3edd5ef5de754861b04320e0 | 98c73e1c03b612cc551f19f8f11205127745c589dc895b7127fa7c2738e6ad4e | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[NH;D2;+0:8]-[C:9](-[C:10])-[C;D1;H3:11]>>[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3])-[C:9](-[C:10])-[C;D1;H3:11] | 95.3 | [{"value": 95.0, "product": "C(C1=CC=CC=C1)OC(N([C@@H](CCC=C)C)CC=C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.3, "product": "C(C1=CC=CC=C1)OC(N([C@@H](CCC=C)C)CC=C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | ((R)-1-Methyl-pent-4-enyl)-carbamic acid benzyl ester (790 mg, 3.39 mmol) was dissolved in DMF (8 ml) and was cooled to 0 degrees C. Sodium hydride (60% dispersion, 271 mg, 6.78 mmol) was added and the reaction was stirred for 15 minutes. Allyl bromide (1.23 g, 0.88 ml, 10.17 mmol) was added and the reaction mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester | Carbamic ester.Allyl | null | null | c1ccccc1 | HBr | O.CN(C)C=O | 0 | 0.25 | C=CCBr.C=CCC[C@@H](C)NC(=O)OCc1ccccc1>O.CN(C)C=O>C=CCC[C@@H](C)N(CC=C)C(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4722a8538f4341518151ae8b4ba6554c | C=CCCC(C)N(CC=C)C(=O)OCc1ccccc1>>CC1CCC=CCN1C(=O)OCc1ccccc1 | C(C1=CC=CC=C1)OC(N(C(CCC=C)C)CC=C)=O>>C(C1=CC=CC=C1)OC(=O)N1C(CCC=CC1)C | C=[CH:5][CH2:4][CH2:3][CH:2]([CH3:1])[N:8]([CH2:7][CH:6]=C)[C:9](=[O:10])[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH:5]=[CH:6][CH2:7][N:8]1[C:9](=[O:10])[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | C=CCCC(C)N(CC=C)C(=O)OCc1ccccc1 | CC1CCC=CCN1C(=O)OCc1ccccc1 | null | C=CC1=CC=CC=C1.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Ru]Cl | C(Cl)Cl | C-C Coupling | OtherReaction | 1c1bcb324a99f1f7cdfad1cda20c60d4247a90d693ba0f29142115753e5db166 | 67a23c4de67c22dcd6bc1d4c033efdcf679af248440c3b10e6768679c5f73280 | O=C(OCc1ccccc1)N1CC=CCCC1 | C=[CH;D2;+0:1]-[C:2]-[#7:3]-[C:4]=[O;D1;H0:5].C=[CH;D2;+0:6]-[C:7]-[C:8]>>[C:8]-[C:7]-[CH;D2;+0:6]=[CH;D2;+0:1]-[C:2]-[#7:3]-[C:4]=[O;D1;H0:5] | 92 | [{"value": 92.0, "product": "C(C1=CC=CC=C1)OC(=O)N1C(CCC=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.0, "product": "C(C1=CC=CC=C1)OC(=O)N1C(CCC=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Allyl-(1-methyl-pent-4-enyl)-carbamic acid benzyl ester (0.872 g, 3.19 mmol) was dissolved in CH2Cl2 (10 ml) and a stream of argon gas was bubbled into the reaction mixture for 10 minutes. Then bis(tricyclohexylphosphine)benzylidine ruthenium(IV) dichloride (Strem Chemicals, Grubbs' catalyst, 19 mg, 0.0227 mmol) was ad... | 10.6084/m9.figshare.5104873.v1 | null | Allyl.Allyl | null | null | C1=CC[NH]CCC1 | C1=CC[NH]CCC1.c1ccccc1 | Other | C=CC1=CC=CC=C1.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Ru]Cl.C(Cl)Cl | null | null | C=CCCC(C)N(CC=C)C(=O)OCc1ccccc1>C=CC1=CC=CC=C1.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Ru]Cl.C(Cl)Cl>CC1CCC=CCN1C(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d98edee6560e4340af4ad7d3892fd3d6 | CC1CCC=CCN1C(=O)OCc1ccccc1>>C[C@@H]1CC[C@@H]2O[C@H]2CN1C(=O)OCc1ccccc1 | ClC1=CC(=CC=C1)C(=O)OO.C(C1=CC=CC=C1)OC(=O)N1C(CCC=CC1)C.ClC1=CC(=CC=C1)C(=O)OO>>C(C1=CC=CC=C1)OC(=O)N1C[C@@H]2O[C@H]2CC[C@H]1C | [CH3:1][CH:2]1[CH2:3][CH2:4][CH:5]=[CH:7][CH2:8][N:9]1[C:10](=[O:11])[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][C@@H:5]2[O:6][C@H:7]2[CH2:8][N:9]1[C:10](=[O:11])[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | CC1CCC=CCN1C(=O)OCc1ccccc1 | C[C@@H]1CC[C@@H]2O[C@H]2CN1C(=O)OCc1ccccc1 | null | null | C(Cl)Cl | Oxidation | OtherReaction | 7be9fb2eb503562d5ea21c3d097422001c85c0fb3ec6af3510a546b05688164f | 064ea107e05241c09a52d804a18982a555fc0def251e05abc9beed7ecad64b38 | O=C(OCc1ccccc1)N1CCC[C@@H]2O[C@H]2C1 | [#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C:6]-[C:7]-[CH;D2;+0:8]=[CH;D2;+0:9]-[C:10]-1>>[#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C:6]-[C:7]-[C@@H;D3;+0:8]2-[#8:11]-[C@H;D3;+0:9]-2-[C:10]-1 | 75 | [{"value": 75.0, "product": "C(C1=CC=CC=C1)OC(=O)N1C[C@@H]2O[C@H]2CC[C@H]1C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.6, "product": "C(C1=CC=CC=C1)OC(=O)N1C[C@@H]2O[C@H]2CC[C@H]1C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | m-Chloro-perbenzoic acid (1.10 g, 57–86% pure) was added to a solution of 2-methyl-2,3,4,7-tetrahydro-azepine-1-carboxylic acid benzyl ester (0.72 g, 2.94 mmol) in CH2Cl2 at 0 degrees C. The reaction mixture was stirred for half an hour, then was warmed to RT. Additional m-chloro-perbenzoic acid (0.660 g, 57–86% pure) ... | 10.6084/m9.figshare.5104873.v1 | null | null | Ether | C1=CC[NH]CCC1 | C1C[NH]C[C@@H]2O[C@H]2C1 | C1C[NH]C[C@@H]2O[C@H]2C1.c1ccccc1 | Other | C(Cl)Cl | null | null | CC1CCC=CCN1C(=O)OCc1ccccc1>C(Cl)Cl>C[C@@H]1CC[C@@H]2O[C@H]2CN1C(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fcb1a0ae49db408e940b2c616037a942 | C[C@@H]1CC[C@H]2O[C@H]2CN1C(=O)OCc1ccccc1.[N-]=[N+]=[N-]>>C[C@@H]1CC[C@H](N=[N+]=[N-])[C@@H](O)CN1C(=O)OCc1ccccc1 | [N-]=[N+]=[N-].[Na+].C(C1=CC=CC=C1)OC(=O)N1C[C@@H]2O[C@@H]2CC[C@H]1C.[Cl-].[NH4+]>>C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@@H]([C@H](C1)O)N=[N+]=[N-])C | [CH3:1][C@@H:2]1[CH2:3][CH2:4][C@@H:5]2[C@@H:9]([O:10]2)[CH2:11][N:12]1[C:13](=[O:14])[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[N-:6]=[N+:7]=[N-:8]>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][C@H:5]([N:6]=[N+:7]=[N-:8])[C@@H:9]([OH:10])[CH2:11][N:12]1[C:13](=[O:14])[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21]... | C[C@@H]1CC[C@H]2O[C@H]2CN1C(=O)OCc1ccccc1.[N-]=[N+]=[N-] | C[C@@H]1CC[C@H](N=[N+]=[N-])[C@@H](O)CN1C(=O)OCc1ccccc1 | null | null | O.CO | Heteroatom Alkylation and Arylation | OtherReaction | 1456e994911707f7df3e98637980691d23a0eb0c7430e6f8999ad88f4b5545a7 | 0de57b50a6157507e9baab9ed62d7e11e29441a6de9ee7172f74a5b142f47048 | O=C(OCc1ccccc1)N1CCCCCC1 | [#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C@@H;D3;+0:6]2-[O;H0;D2;+0:7]-[C@@H;D3;+0:8]-2-[C:9]-[C:10]-[C:11]-1.[N-;H0;D1:12]=[#7;+:13]=[N;-;D1;H0:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C@H;D3;+0:6](-[OH;D1;+0:7])-[C@@H;D3;+0:8](-[N;H0;D2;+0:12]=[#7;+:13]=[N;-;D1;H0:14])-[C:9]-[C:10]-[C:11]-1 | 89 | [{"value": 89.0, "product": "C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@@H]([C@H](C1)O)N=[N+]=[N-])C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.9, "product": "C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@@H]([C@H](C1)O)N=[N+]=[N-])C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Sodium azide (0.139 g, 2.14 mmol) was added to a solution of (1S,4R,7R)-4-methyl-8-oxa-3-aza-bicyclo[5.1.0]octane-3-carboxylic acid benzyl ester (0.186 g, 0.71 mmol) and ammonium chloride (0.114 g, 2.14 mmol) in MeOH (1.5 ml) and H2O (0.15 ml), then was refluxed for 6 h. The reaction mixture was concentrated in vacuo b... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Azide.Secondary alcohol | C1C[NH]C[C@@H]2O[C@@H]2C1 | C1CCC[NH]CC1 | C1CCC[NH]CC1.c1ccccc1 | null | O.CO | null | null | C[C@@H]1CC[C@H]2O[C@H]2CN1C(=O)OCc1ccccc1.[N-]=[N+]=[N-]>O.CO>C[C@@H]1CC[C@H](N=[N+]=[N-])[C@@H](O)CN1C(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c6c3b8d32bb04091a0ca7f5b6bfe9581 | C[C@@H]1CC[C@H](N=[N+]=[N-])[C@@H](O)CN1C(=O)OCc1ccccc1>>C[C@@H]1CC[C@H](N)[C@@H](O)CN1C(=O)OCc1ccccc1 | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@@H]([C@H](C1)O)N=[N+]=[N-])C>>C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@@H]([C@H](C1)O)N)C | [N-]=[N+]=[N:6][C@H:5]1[CH2:4][CH2:3][C@@H:2]([CH3:1])[N:10]([C:11](=[O:12])[O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:9][C@@H:7]1[OH:8]>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][C@H:5]([NH2:6])[C@@H:7]([OH:8])[CH2:9][N:10]1[C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | C[C@@H]1CC[C@H](N=[N+]=[N-])[C@@H](O)CN1C(=O)OCc1ccccc1 | C[C@@H]1CC[C@H](N)[C@@H](O)CN1C(=O)OCc1ccccc1 | null | null | O.C1(=CC=CC=C1)C.C1CCOC1 | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | O=C(OCc1ccccc1)N1CCCCCC1 | [C:1]-[C:2](-[N;H0;D2;+0:3]=[N+]=[N-])-[C:4]>>[C:1]-[C:2](-[NH2;D1;+0:3])-[C:4] | null | [] | 45 | CELSIUS | null | null | Triphenylphosphine (0.25 g, 0.952 mmol) was added to a solution of (2R,5S,6S)-5-azido-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl ester (0.193 g, 0.635 mmol) in THF (10 ml) and H2O (0.04 ml), then was heated to 45 degrees C. overnight. The reaction mixture was then diluted with toluene (100 ml×2) and was azeotr... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | C1CCC[NH]CC1.c1ccccc1 | Other | O.C1(=CC=CC=C1)C.C1CCOC1 | 45 | null | C[C@@H]1CC[C@H](N=[N+]=[N-])[C@@H](O)CN1C(=O)OCc1ccccc1>O.C1(=CC=CC=C1)C.C1CCOC1>C[C@@H]1CC[C@H](N)[C@@H](O)CN1C(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ff1d792039b841c7826edddb51f2b6a9 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)O.CC1CCC(N)C(O)CN1C(=O)OCc1ccccc1>>CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)N(C(=O)OCc2ccccc2)C[C@@H]1O | CN(CCCN=C=NCC)C.O.C(=O)(OC(C)(C)C)N[C@@H](CC(C)C)C(=O)O.OC1=CC=CC=2NN=NC21.C(C1=CC=CC=C1)OC(=O)N1C(CCC(C(C1)O)N)C>>C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@@H]([C@H](C1)O)NC([C@H](CC(C)C)NC(=O)OC(C)(C)C)=O)C | O[C:14]([C@H:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:15].[NH2:16][CH:17]1[CH2:18][CH2:19][CH:20]([CH3:21])[N:22]([C:23](=[O:24])[O:25][CH2:26][c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[CH2:33][CH:34]1[OH:35]>>[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH:6][C:7](=[O:... | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)O.CC1CCC(N)C(O)CN1C(=O)OCc1ccccc1 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)N(C(=O)OCc2ccccc2)C[C@@H]1O | null | null | CN(C)C=O.CCOC(=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(OCc1ccccc1)N1CCCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[#8:13]-[C:14](=[O;D1;H0:15])-[#7:16]1-[C:17]-[C:18]-[C:19]-[CH;D3;+0:20](-[NH2;D1;+0:21])-[CH;D3;+0:22](-[O;D1;H1:23])-[C:24]-1>>[#8:13]-[C:14](=[O;D1;H0:15])-[#7:16]1-[C:17]-[C:18]-[C:19]-[C... | 77.8 | [{"value": 72.0, "product": "C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@@H]([C@H](C1)O)NC([C@H](CC(C)C)NC(=O)OC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.8, "product": "C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@@H]([C@H](C1)O)NC([C@H](CC(C)C)NC(=O)OC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "... | null | null | 8 | HOUR | 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide (0.164 g, 0.22 mmol) was added to a solution of Boc-Leucine-hydrate (0.190 g, 0.76 mmol), diisopropyletbylamine (0.164 g, 0.22 ml, 1.27 mmol), hydroxybenztriazole (0.114 g, 0.83 mmol), and racemic (2R,5S,6S)-5-Amino-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl ester ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CCC[NH]CC1.c1ccccc1 | HO- | CN(C)C=O.CCOC(=O)C | null | 8 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)O.CC1CCC(N)C(O)CN1C(=O)OCc1ccccc1>CN(C)C=O.CCOC(=O)C>CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)N(C(=O)OCc2ccccc2)C[C@@H]1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-65dfd71e9fca499fa306b0e0f6ceb081 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)N(C(=O)OCc2ccccc2)C[C@@H]1O>>CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NC[C@@H]1O | C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@@H]([C@H](C1)O)NC([C@H](CC(C)C)NC(=O)OC(C)(C)C)=O)C.CO.[H][H]>>C(C)(C)(C)OC(N[C@@H](CC(C)C)C(N[C@@H]1[C@H](CN[C@@H](CC1)C)O)=O)=O | O=C(OCc1ccccc1)[N:22]1[C@H:20]([CH3:21])[CH2:19][CH2:18][C@H:17]([NH:16][C:14]([C@H:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:15])[C@@H:24]([OH:25])[CH2:23]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[C:14](=[O:... | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)N(C(=O)OCc2ccccc2)C[C@@H]1O | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NC[C@@H]1O | null | [Pd] | CCOC(=O)C | Reduction | Hydrogenolysis of tertiary amines | 4baebb2e24e86e84182af36602f2110147b788036582af3484a3c912f0e742fe | 20c36f41eeb07c3ba4437b51ba72e8ff3c22d0b27e7197b0e9af3127f331149f | C1CCCNCC1 | O=C(-O-C-c1:c:c:c:c:c:1)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4](-[C;D1;H3:5])-[C:6]>>[C:6]-[C:4](-[C;D1;H3:5])-[NH;D2;+0:1]-[C:2]-[C:3] | null | [] | null | null | 8 | HOUR | (2R,5S,6S)-5-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl ester (0.169 g, 0.344 mmol) was dissolved in EtOAc (3 ml), MeOH (1 ml). Then 10% Pd/C (0.183 g, 0.172 mmol) was added and the reaction was stirred overnight under a balloon filled with hydrogen gas.... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Secondary amine | c1ccccc1.C1CCC[NH]CC1 | C1CCCNCC1 | C1CCCNCC1 | HO- | [Pd].CCOC(=O)C | null | 8 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)N(C(=O)OCc2ccccc2)C[C@@H]1O>[Pd].CCOC(=O)C>CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NC[C@@H]1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d3a35e6828ad48febd6463d7902cda6b | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NC[C@@H]1O.O=S(=O)(Cl)c1ccccn1>>CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NC(S(=O)(=O)c2ccccn2)[C@H]1O | N1=C(C=CC=C1)S(=O)(=O)Cl.C(C)(C)(C)OC(N[C@@H](CC(C)C)C(N[C@@H]1[C@H](CN[C@@H](CC1)C)O)=O)=O.C([O-])(O)=O.[Na+]>>C(C)(C)(C)OC(N[C@@H](CC(C)C)C(N[C@@H]1[C@@H](C(N[C@@H](CC1)C)S(=O)(=O)C1=NC=CC=C1)O)=O)=O | [CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[C:14](=[O:15])[NH:16][C@H:17]1[CH2:18][CH2:19][C@@H:20]([CH3:21])[NH:22][CH2:23][C@@H:33]1[OH:34].Cl[S:24](=[O:25])(=[O:26])[c:27]1[cH:28][cH:29][cH:30][cH:31][n:32]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH:6][C:7](=[O:8]... | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NC[C@@H]1O.O=S(=O)(Cl)c1ccccn1 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NC(S(=O)(=O)c2ccccn2)[C@H]1O | null | null | O.C(Cl)Cl.CCOC(=O)C | Acylation | OtherReaction | 50e15e487d082133a2541b580d202e111d159447d72a96166c5be5a0b31d1f2a | 12e26711b9e38871791ea5f59b3bfb71dff01e8154858e262eb9cd0332ab4fee | O=S(=O)(c1ccccn1)C1CCCCCN1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#7;a:6]:[c:7].[C:8]-[C:9](-[O;D1;H1:10])-[CH2;D2;+0:11]-[#7:12]-[C:13]>>[C:8]-[C:9](-[O;D1;H1:10])-[CH;D3;+0:11](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#7;a:6]:[c:7])-[#7:12]-[C:13] | 104.9 | [{"value": 70.0, "product": "C(C)(C)(C)OC(N[C@@H](CC(C)C)C(N[C@@H]1[C@@H](C(N[C@@H](CC1)C)S(=O)(=O)C1=NC=CC=C1)O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 104.9, "product": "C(C)(C)(C)OC(N[C@@H](CC(C)C)C(N[C@@H]1[C@@H](C(N[C@@H](CC1)C)S(=O)(=O)C1=NC=CC=C1)O)=O)=O", "details": "CALCULATEDPERCENT... | null | null | 30 | MINUTE | 2-Pyridine sulfonyl chloride (0.71 g, 0.4 mmol) was added to a solution of [(S)-1-((3S,4S,7R)-3-hydroxy-7-methyl-azepan-4-ylcarbamoyl)-3-methyl-butyl]-carbamic acid tert-butyl ester (0.126 g, 0.344 mmol), sodium bicarbonate (0.87 g, 1.03 mmol) in CH2Cl2 (3 ml) and H2O (2 ml) and was stirred at RT for 30 minutes. The re... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Sulfone | C1CCCNCC1 | C1CCCNCC1 | C1CCCNCC1.c1ccncc1 | HCl | O.C(Cl)Cl.CCOC(=O)C | null | 0.5 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NC[C@@H]1O.O=S(=O)(Cl)c1ccccn1>O.C(Cl)Cl.CCOC(=O)C>CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NC(S(=O)(=O)c2ccccn2)[C@H]1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a61010e449fd45c1bcf28585c837c682 | CC(C)C[C@H](NC(=O)c1cc2ccccc2o1)C(=O)N[C@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)C[C@@H]1O>>CC(C)C[C@H](NC(=O)c1cc2ccccc2o1)C(=O)N[C@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)CC1=O | CC(=O)OI1(C=2C=CC=CC2C(=O)O1)(OC(=O)C)OC(=O)C.O[C@H]1CN([C@@H](CC[C@@H]1NC(=O)[C@H](CC(C)C)NC(=O)C=1OC2=C(C1)C=CC=C2)C)S(=O)(=O)C2=NC=CC=C2>>CC(C[C@@H](C(N[C@@H]1C(CN([C@@H](CC1)C)S(=O)(=O)C1=NC=CC=C1)=O)=O)NC(=O)C=1OC2=C(C1)C=CC=C2)C | [CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH:6][C:7](=[O:8])[c:9]1[cH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[o:17]1)[C:18](=[O:19])[NH:20][C@H:21]1[CH2:22][CH2:23][C@@H:24]([CH3:25])[N:26]([S:27](=[O:28])(=[O:29])[c:30]2[cH:31][cH:32][cH:33][cH:34][n:35]2)[CH2:36][C@@H:37]1[OH:38]>>[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:... | CC(C)C[C@H](NC(=O)c1cc2ccccc2o1)C(=O)N[C@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)C[C@@H]1O | CC(C)C[C@H](NC(=O)c1cc2ccccc2o1)C(=O)N[C@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)CC1=O | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 14b488e4129d7de2d07ca6b39e641a5c8222ffe6452ab415aeabbdbcc777a2ba | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C(CNC(=O)c1cc2ccccc2o1)N[C@H]1CCCN(S(=O)(=O)c2ccccn2)CC1=O | [#16:1]-[#7:2](-[C:3])-[C:4]-[C@H;D3;+0:5](-[OH;D1;+0:6])-[C:7](-[#7:8]-[C:9]=[O;D1;H0:10])-[C:11]>>[#16:1]-[#7:2](-[C:3])-[C:4]-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-[C:7](-[#7:8]-[C:9]=[O;D1;H0:10])-[C:11] | 97 | [{"value": 97.0, "product": "CC(C[C@@H](C(N[C@@H]1C(CN([C@@H](CC1)C)S(=O)(=O)C1=NC=CC=C1)=O)=O)NC(=O)C=1OC2=C(C1)C=CC=C2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.8, "product": "CC(C[C@@H](C(N[C@@H]1C(CN([C@@H](CC1)C)S(=O)(=O)C1=NC=CC=C1)=O)=O)NC(=O)C=1OC2=C(C1)C=CC=C2)C", "details": "CALCULATED... | null | null | null | null | Dess-Martin periodinane (0.077 g, 0.182 mmol) was added to a solution of. Benzofuran-2-carboxylic acid {(S)-1-[(3S,4S,7R)-3-hydroxy-7-methyl-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-3-methyl-butyl}-amide (0.058 g, 0.107 mmol) in CH2Cl2 (10 ml) and was stirred at RT for 1 h. The solution was washed with 10% aq. Na2... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | C1CCC[NH]CC1 | C1CCC[NH]CC1 | c1ccc2occc2c1.C1CCC[NH]CC1.c1ccncc1 | null | C(Cl)Cl | null | null | CC(C)C[C@H](NC(=O)c1cc2ccccc2o1)C(=O)N[C@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)C[C@@H]1O>C(Cl)Cl>CC(C)C[C@H](NC(=O)c1cc2ccccc2o1)C(=O)N[C@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)CC1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5352f07aef734b8c929717baa9624941 | C[C@H](CO)NC(=O)OCc1ccccc1.II>>C[C@H](CI)NC(=O)OCc1ccccc1 | C(C1=CC=CC=C1)OC(N[C@@H](CO)C)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N1C=NC=C1.II>>C(C1=CC=CC=C1)OC(N[C@@H](CI)C)=O | O[CH2:3][C@@H:2]([CH3:1])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.I[I:4]>>[CH3:1][C@H:2]([CH2:3][I:4])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | C[C@H](CO)NC(=O)OCc1ccccc1.II | C[C@H](CI)NC(=O)OCc1ccccc1 | null | null | O.C(Cl)Cl | Functional Group Interconversion | OtherReaction | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccccc1 | I-[I;H0;D1;+0:1].O-[CH2;D2;+0:2]-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7]>>[C;D1;H3:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[CH2;D2;+0:2]-[I;H0;D1;+0:1] | null | [] | 0 | CELSIUS | 3 | HOUR | Triphenylphospine (24 g, 91.8 mmol) was added to a solution of imidazole (12.5 g, 184 mmol) in CH2Cl2 (231 ml), then was cooled to 0 degrees C. Iodine (23.3 g, 91.8 mmol) was added to the suspension. The reaction mixture turned yellow, then faintly brown. After 5 minutes ((R)-2-hydroxy-1-methyl-ethyl)-carbamic acid ben... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccccc1 | HI | O.C(Cl)Cl | 0 | 3 | C[C@H](CO)NC(=O)OCc1ccccc1.II>O.C(Cl)Cl>C[C@H](CI)NC(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8c03ae629f2b4b1baa297a5e2dc41c15 | C=C[CH2][Mg][Cl].C[C@H](CI)NC(=O)OCc1ccccc1>>C=CCC[C@@H](C)NC(=O)OCc1ccccc1 | C(C=C)[Mg]Cl.C(C1=CC=CC=C1)OC(N[C@@H](CI)C)=O>>C(C1=CC=CC=C1)OC(N[C@@H](CCC=C)C)=O | [Cl][Mg][CH2:3][CH:2]=[CH2:1].I[CH2:4][C@@H:5]([CH3:6])[NH:7][C:8](=[O:9])[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][C@@H:5]([CH3:6])[NH:7][C:8](=[O:9])[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | C=C[CH2][Mg][Cl].C[C@H](CI)NC(=O)OCc1ccccc1 | C=CCC[C@@H](C)NC(=O)OCc1ccccc1 | null | CSC.[Cu]Br | C1CCOC1 | C-C Coupling | OtherReaction | 95388f86cfea993e1d805de665d94c100ee3193d1978ecc8dd5e389bef693379 | d05251cf430cdb8f7fa37cdc312f93d4b47af4d8ed879f979cecc41cba4e1db9 | c1ccccc1 | I-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])-[#7:4]-[C:5]=[O;D1;H0:6].[C;D1;H2:7]=[C:8]-[CH2;D2;+0:9]-[Mg]-[Cl]>>[C;D1;H2:7]=[C:8]-[CH2;D2;+0:9]-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])-[#7:4]-[C:5]=[O;D1;H0:6] | null | [] | -78 | CELSIUS | 30 | MINUTE | Copper (I) bromide-dimethyl sulfide (1.93 g, 9.4 mmol) was dissolved in distilled THF (24 ml), then was cooled to −78 degrees C. A solution of allyl magnesium chloride (9.4 ml, 2M in THF, Aldrich) was added dropwise, then the solution was stirred for 30 minutes. ((R)-2-Iodo-1-methyl-ethyl)-carbamic acid benzyl ester (1... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Primary halide.Allyl | Allyl | null | null | c1ccccc1 | I-.Mg | CSC.[Cu]Br.C1CCOC1 | -78 | 0.5 | C=C[CH2][Mg][Cl].C[C@H](CI)NC(=O)OCc1ccccc1>CSC.[Cu]Br.C1CCOC1>C=CCC[C@@H](C)NC(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7494b5e9cd224a229428c5788b97ee4c | C=CCBr.C=CCC[C@@H](C)NC(=O)OCc1ccccc1>>C=CCC[C@@H](C)N(CC=C)C(=O)OCc1ccccc1 | Cl.[H-].[Na+].C(C1=CC=CC=C1)OC(N[C@@H](CCC=C)C)=O.C(C=C)Br>>C(C1=CC=CC=C1)OC(N([C@@H](CCC=C)C)CC=C)=O | Br[CH2:8][CH:9]=[CH2:10].[CH2:1]=[CH:2][CH2:3][CH2:4][C@@H:5]([CH3:6])[NH:7][C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][C@@H:5]([CH3:6])[N:7]([CH2:8][CH:9]=[CH2:10])[C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | C=CCBr.C=CCC[C@@H](C)NC(=O)OCc1ccccc1 | C=CCC[C@@H](C)N(CC=C)C(=O)OCc1ccccc1 | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 9f7a278cd5a191722d3eecc8371d7231da3fad2a3edd5ef5de754861b04320e0 | 98c73e1c03b612cc551f19f8f11205127745c589dc895b7127fa7c2738e6ad4e | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[NH;D2;+0:8]-[C:9](-[C:10])-[C;D1;H3:11]>>[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3])-[C:9](-[C:10])-[C;D1;H3:11] | 95.3 | [{"value": 95.0, "product": "C(C1=CC=CC=C1)OC(N([C@@H](CCC=C)C)CC=C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.3, "product": "C(C1=CC=CC=C1)OC(N([C@@H](CCC=C)C)CC=C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | ((R)-1-Methyl-pent-4-enyl)-carbamic acid benzyl ester (790 mg, 3.39 mmol) was dissolved in DMF (8 ml) and was cooled to 0 degrees C. Sodium hydride (60% dispersion, 271 mg, 6.78 mmol) was added and the reaction was stirred for 15 minutes. Allyl bromide (1.23 g, 0.88 ml, 10.17 mmol) was added and the reaction mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester | Carbamic ester.Allyl | null | null | c1ccccc1 | HBr | O.CN(C)C=O | 0 | 0.25 | C=CCBr.C=CCC[C@@H](C)NC(=O)OCc1ccccc1>O.CN(C)C=O>C=CCC[C@@H](C)N(CC=C)C(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-69f9e43c13ef4126a58555e898d3ae2e | C=CCCC(C)N(CC=C)C(=O)OCc1ccccc1>>CC1CCC=CCN1C(=O)OCc1ccccc1 | C(C1=CC=CC=C1)OC(N(C(CCC=C)C)CC=C)=O>>C(C1=CC=CC=C1)OC(=O)N1C(CCC=CC1)C | C=[CH:5][CH2:4][CH2:3][CH:2]([CH3:1])[N:8]([CH2:7][CH:6]=C)[C:9](=[O:10])[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH:5]=[CH:6][CH2:7][N:8]1[C:9](=[O:10])[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | C=CCCC(C)N(CC=C)C(=O)OCc1ccccc1 | CC1CCC=CCN1C(=O)OCc1ccccc1 | null | C=CC1=CC=CC=C1.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Ru]Cl.C=CC1=CC=CC=C1.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Ru]Cl | C(Cl)Cl | C-C Coupling | OtherReaction | 1c1bcb324a99f1f7cdfad1cda20c60d4247a90d693ba0f29142115753e5db166 | 67a23c4de67c22dcd6bc1d4c033efdcf679af248440c3b10e6768679c5f73280 | O=C(OCc1ccccc1)N1CC=CCCC1 | C=[CH;D2;+0:1]-[C:2]-[#7:3]-[C:4]=[O;D1;H0:5].C=[CH;D2;+0:6]-[C:7]-[C:8]>>[C:8]-[C:7]-[CH;D2;+0:6]=[CH;D2;+0:1]-[C:2]-[#7:3]-[C:4]=[O;D1;H0:5] | 92 | [{"value": 92.0, "product": "C(C1=CC=CC=C1)OC(=O)N1C(CCC=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.0, "product": "C(C1=CC=CC=C1)OC(=O)N1C(CCC=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Allyl-(1-methyl-pent-4-enyl)-carbamic acid benzyl ester (0.872 g, 3.19 mmol) was dissolved in CH2Cl2 (10 ml) and a stream of argon gas was bubbled into the reaction mixture for 10 minutes. Then bis(tricyclohexylphosphine)benzylidine ruthenium(IV) dichloride (Strem Chemicals, Grubbs' catalyst, 19 mg, 0.0227 mmol) was ad... | 10.6084/m9.figshare.5104873.v1 | null | Allyl.Allyl | null | null | C1=CC[NH]CCC1 | C1=CC[NH]CCC1.c1ccccc1 | Other | C=CC1=CC=CC=C1.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Ru]Cl.C=CC1=CC=CC=C1.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Ru]Cl.C(Cl)Cl | null | null | C=CCCC(C)N(CC=C)C(=O)OCc1ccccc1>C=CC1=CC=CC=C1.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Ru]Cl.C=CC1=CC=CC=C1.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Ru]Cl.C(Cl)Cl>CC1CCC=CCN1C(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-db1c8f9538dc4458a604763c0c0d5322 | CC1CCC=CCN1C(=O)OCc1ccccc1>>C[C@@H]1CC[C@@H]2O[C@H]2CN1C(=O)OCc1ccccc1 | ClC1=CC(=CC=C1)C(=O)OO.C(C1=CC=CC=C1)OC(=O)N1C(CCC=CC1)C.ClC1=CC(=CC=C1)C(=O)OO>>C(C1=CC=CC=C1)OC(=O)N1C[C@@H]2O[C@H]2CC[C@H]1C | [CH3:1][CH:2]1[CH2:3][CH2:4][CH:5]=[CH:7][CH2:8][N:9]1[C:10](=[O:11])[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][C@@H:5]2[O:6][C@H:7]2[CH2:8][N:9]1[C:10](=[O:11])[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | CC1CCC=CCN1C(=O)OCc1ccccc1 | C[C@@H]1CC[C@@H]2O[C@H]2CN1C(=O)OCc1ccccc1 | null | null | C(Cl)Cl | Oxidation | OtherReaction | 7be9fb2eb503562d5ea21c3d097422001c85c0fb3ec6af3510a546b05688164f | 064ea107e05241c09a52d804a18982a555fc0def251e05abc9beed7ecad64b38 | O=C(OCc1ccccc1)N1CCC[C@@H]2O[C@H]2C1 | [#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C:6]-[C:7]-[CH;D2;+0:8]=[CH;D2;+0:9]-[C:10]-1>>[#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C:6]-[C:7]-[C@@H;D3;+0:8]2-[#8:11]-[C@H;D3;+0:9]-2-[C:10]-1 | 75 | [{"value": 75.0, "product": "C(C1=CC=CC=C1)OC(=O)N1C[C@@H]2O[C@H]2CC[C@H]1C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.6, "product": "C(C1=CC=CC=C1)OC(=O)N1C[C@@H]2O[C@H]2CC[C@H]1C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | m-Chloro-perbenzoic acid (1.10 g, 57–86% pure) was added to a solution of 2-methyl-2,3,4,7-tetrahydro-azepine-1-carboxylic acid benzyl ester (0.72 g, 2.94 mmol) in CH2Cl2 at 0 degrees C. The reaction mixture was stirred for half an hour, then was warmed to RT. Additional m-chloro-perbenzoic acid (0.660 g, 57–86% pure) ... | 10.6084/m9.figshare.5104873.v1 | null | null | Ether | C1=CC[NH]CCC1 | C1C[NH]C[C@@H]2O[C@H]2C1 | C1C[NH]C[C@@H]2O[C@H]2C1.c1ccccc1 | Other | C(Cl)Cl | null | null | CC1CCC=CCN1C(=O)OCc1ccccc1>C(Cl)Cl>C[C@@H]1CC[C@@H]2O[C@H]2CN1C(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f5167c19eb6d405c82f7304c5fcc9080 | C[C@@H]1CC[C@H]2O[C@H]2CN1C(=O)OCc1ccccc1.[N-]=[N+]=[N-]>>C[C@@H]1CC[C@H](N=[N+]=[N-])[C@@H](O)CN1C(=O)OCc1ccccc1 | [N-]=[N+]=[N-].[Na+].C(C1=CC=CC=C1)OC(=O)N1C[C@@H]2O[C@@H]2CC[C@H]1C.[Cl-].[NH4+]>>C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@@H]([C@H](C1)O)N=[N+]=[N-])C | [CH3:1][C@@H:2]1[CH2:3][CH2:4][C@@H:5]2[C@@H:9]([O:10]2)[CH2:11][N:12]1[C:13](=[O:14])[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[N-:6]=[N+:7]=[N-:8]>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][C@H:5]([N:6]=[N+:7]=[N-:8])[C@@H:9]([OH:10])[CH2:11][N:12]1[C:13](=[O:14])[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21]... | C[C@@H]1CC[C@H]2O[C@H]2CN1C(=O)OCc1ccccc1.[N-]=[N+]=[N-] | C[C@@H]1CC[C@H](N=[N+]=[N-])[C@@H](O)CN1C(=O)OCc1ccccc1 | null | null | O.CO | Heteroatom Alkylation and Arylation | OtherReaction | 1456e994911707f7df3e98637980691d23a0eb0c7430e6f8999ad88f4b5545a7 | 0de57b50a6157507e9baab9ed62d7e11e29441a6de9ee7172f74a5b142f47048 | O=C(OCc1ccccc1)N1CCCCCC1 | [#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C@@H;D3;+0:6]2-[O;H0;D2;+0:7]-[C@@H;D3;+0:8]-2-[C:9]-[C:10]-[C:11]-1.[N-;H0;D1:12]=[#7;+:13]=[N;-;D1;H0:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C@H;D3;+0:6](-[OH;D1;+0:7])-[C@@H;D3;+0:8](-[N;H0;D2;+0:12]=[#7;+:13]=[N;-;D1;H0:14])-[C:9]-[C:10]-[C:11]-1 | 89 | [{"value": 89.0, "product": "C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@@H]([C@H](C1)O)N=[N+]=[N-])C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.9, "product": "C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@@H]([C@H](C1)O)N=[N+]=[N-])C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Sodium azide (0.139 g, 2.14 mmol) was added to a solution of (1S,4R,7R)-4-methyl-8-oxa-3-aza-bicyclo[5.1.0]octane-3-carboxylic acid benzyl ester (0.186 g, 0.71 mmol) and ammonium chloride (0.114 g, 2.14 mmol) in MeOH (1.5 ml) and H2O (0.15 ml), then was refluxed for 6 h. The reaction mixture was concentrated in vacuo b... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Azide.Secondary alcohol | C1C[NH]C[C@@H]2O[C@@H]2C1 | C1CCC[NH]CC1 | C1CCC[NH]CC1.c1ccccc1 | null | O.CO | null | null | C[C@@H]1CC[C@H]2O[C@H]2CN1C(=O)OCc1ccccc1.[N-]=[N+]=[N-]>O.CO>C[C@@H]1CC[C@H](N=[N+]=[N-])[C@@H](O)CN1C(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fea91506f17c41df876203a3b1629bd1 | C[C@@H]1CC[C@H](N=[N+]=[N-])[C@@H](O)CN1C(=O)OCc1ccccc1>>C[C@@H]1CC[C@H](N)[C@@H](O)CN1C(=O)OCc1ccccc1 | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@@H]([C@H](C1)O)N=[N+]=[N-])C>>C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@@H]([C@H](C1)O)N)C | [N-]=[N+]=[N:6][C@H:5]1[CH2:4][CH2:3][C@@H:2]([CH3:1])[N:10]([C:11](=[O:12])[O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:9][C@@H:7]1[OH:8]>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][C@H:5]([NH2:6])[C@@H:7]([OH:8])[CH2:9][N:10]1[C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | C[C@@H]1CC[C@H](N=[N+]=[N-])[C@@H](O)CN1C(=O)OCc1ccccc1 | C[C@@H]1CC[C@H](N)[C@@H](O)CN1C(=O)OCc1ccccc1 | null | null | O.C1(=CC=CC=C1)C.C1CCOC1 | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | O=C(OCc1ccccc1)N1CCCCCC1 | [C:1]-[C:2](-[N;H0;D2;+0:3]=[N+]=[N-])-[C:4]>>[C:1]-[C:2](-[NH2;D1;+0:3])-[C:4] | null | [] | 45 | CELSIUS | null | null | Triphenylphosphine (0.25 g, 0.952 mmol) was added to a solution of (2R,5S,6S)-5-azido-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl ester (0.193 g, 0.635 mmol) in THF (10 ml) and H2O (0.04 ml), then was heated to 45 degrees C. overnight. The reaction mixture was then diluted with toluene (100 ml×2) and was azeotr... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | C1CCC[NH]CC1.c1ccccc1 | Other | O.C1(=CC=CC=C1)C.C1CCOC1 | 45 | null | C[C@@H]1CC[C@H](N=[N+]=[N-])[C@@H](O)CN1C(=O)OCc1ccccc1>O.C1(=CC=CC=C1)C.C1CCOC1>C[C@@H]1CC[C@H](N)[C@@H](O)CN1C(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1979e234a1ee4adf9c87b529f0dc8950 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)O.CC1CCC(N)C(O)CN1C(=O)OCc1ccccc1>>CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)N(C(=O)OCc2ccccc2)C[C@@H]1O | CN(CCCN=C=NCC)C.O.C(=O)(OC(C)(C)C)N[C@@H](CC(C)C)C(=O)O.C(C)(C)N(CC)C(C)C.OC1=CC=CC=2NN=NC21.C(C1=CC=CC=C1)OC(=O)N1C(CCC(C(C1)O)N)C>>C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@@H]([C@H](C1)O)NC([C@H](CC(C)C)NC(=O)OC(C)(C)C)=O)C | O[C:14]([C@H:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:15].[NH2:16][CH:17]1[CH2:18][CH2:19][CH:20]([CH3:21])[N:22]([C:23](=[O:24])[O:25][CH2:26][c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[CH2:33][CH:34]1[OH:35]>>[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH:6][C:7](=[O:... | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)O.CC1CCC(N)C(O)CN1C(=O)OCc1ccccc1 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)N(C(=O)OCc2ccccc2)C[C@@H]1O | null | null | CN(C)C=O.CCOC(=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(OCc1ccccc1)N1CCCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[#8:13]-[C:14](=[O;D1;H0:15])-[#7:16]1-[C:17]-[C:18]-[C:19]-[CH;D3;+0:20](-[NH2;D1;+0:21])-[CH;D3;+0:22](-[O;D1;H1:23])-[C:24]-1>>[#8:13]-[C:14](=[O;D1;H0:15])-[#7:16]1-[C:17]-[C:18]-[C:19]-[C... | 77.8 | [{"value": 72.0, "product": "C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@@H]([C@H](C1)O)NC([C@H](CC(C)C)NC(=O)OC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.8, "product": "C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@@H]([C@H](C1)O)NC([C@H](CC(C)C)NC(=O)OC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "... | null | null | 8 | HOUR | 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide (0.164 g, 0.22 mmol) was added to a solution of Boc-Leucine-hydrate (0.190 g, 0.76 mmol), diisopropylethylamine (0.164 g, 0.22 ml, 1.27 mmol), hydroxybenztriazole (0.114 g, 0.83 mmol), and racemic (2R,5S,6S)-5-Amino-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl ester ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CCC[NH]CC1.c1ccccc1 | HO- | CN(C)C=O.CCOC(=O)C | null | 8 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)O.CC1CCC(N)C(O)CN1C(=O)OCc1ccccc1>CN(C)C=O.CCOC(=O)C>CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)N(C(=O)OCc2ccccc2)C[C@@H]1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4f3a21928c6f4400b617ab434224ecf6 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)N(C(=O)OCc2ccccc2)C[C@@H]1O>>CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NC[C@@H]1O | C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@@H]([C@H](C1)O)NC([C@H](CC(C)C)NC(=O)OC(C)(C)C)=O)C.CO.[H][H]>>C(C)(C)(C)OC(N[C@@H](CC(C)C)C(N[C@@H]1[C@H](CN[C@@H](CC1)C)O)=O)=O | O=C(OCc1ccccc1)[N:22]1[C@H:20]([CH3:21])[CH2:19][CH2:18][C@H:17]([NH:16][C:14]([C@H:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:15])[C@@H:24]([OH:25])[CH2:23]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[C:14](=[O:... | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)N(C(=O)OCc2ccccc2)C[C@@H]1O | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NC[C@@H]1O | null | [Pd] | CCOC(=O)C | Reduction | Hydrogenolysis of tertiary amines | 4baebb2e24e86e84182af36602f2110147b788036582af3484a3c912f0e742fe | 20c36f41eeb07c3ba4437b51ba72e8ff3c22d0b27e7197b0e9af3127f331149f | C1CCCNCC1 | O=C(-O-C-c1:c:c:c:c:c:1)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4](-[C;D1;H3:5])-[C:6]>>[C:6]-[C:4](-[C;D1;H3:5])-[NH;D2;+0:1]-[C:2]-[C:3] | null | [] | null | null | 8 | HOUR | (2R,5S,6S)-5-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl ester (0.169 g, 0.344 mmol) was dissovled in EtOAc (3 ml), MeOH (1 ml). Then 10% Pd/C (0.183 g, 0.172 mmol) was added and the reaction was stirred overnight under a balloon filled with hydrogen gas.... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Secondary amine | c1ccccc1.C1CCC[NH]CC1 | C1CCCNCC1 | C1CCCNCC1 | HO- | [Pd].CCOC(=O)C | null | 8 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)N(C(=O)OCc2ccccc2)C[C@@H]1O>[Pd].CCOC(=O)C>CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NC[C@@H]1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8c259c949a3d4a53acbba04f97db6e1c | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NC[C@@H]1O.O=S(=O)(Cl)c1ccccn1>>CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NC(S(=O)(=O)c2ccccn2)[C@H]1O | N1=C(C=CC=C1)S(=O)(=O)Cl.C(C)(C)(C)OC(N[C@@H](CC(C)C)C(N[C@@H]1[C@H](CN[C@@H](CC1)C)O)=O)=O.C([O-])(O)=O.[Na+]>>C(C)(C)(C)OC(N[C@@H](CC(C)C)C(N[C@@H]1[C@@H](C(N[C@@H](CC1)C)S(=O)(=O)C1=NC=CC=C1)O)=O)=O | [CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[C:14](=[O:15])[NH:16][C@H:17]1[CH2:18][CH2:19][C@@H:20]([CH3:21])[NH:22][CH2:23][C@@H:33]1[OH:34].Cl[S:24](=[O:25])(=[O:26])[c:27]1[cH:28][cH:29][cH:30][cH:31][n:32]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH:6][C:7](=[O:8]... | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NC[C@@H]1O.O=S(=O)(Cl)c1ccccn1 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NC(S(=O)(=O)c2ccccn2)[C@H]1O | null | null | O.C(Cl)Cl.CCOC(=O)C | Acylation | OtherReaction | 50e15e487d082133a2541b580d202e111d159447d72a96166c5be5a0b31d1f2a | 12e26711b9e38871791ea5f59b3bfb71dff01e8154858e262eb9cd0332ab4fee | O=S(=O)(c1ccccn1)C1CCCCCN1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#7;a:6]:[c:7].[C:8]-[C:9](-[O;D1;H1:10])-[CH2;D2;+0:11]-[#7:12]-[C:13]>>[C:8]-[C:9](-[O;D1;H1:10])-[CH;D3;+0:11](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#7;a:6]:[c:7])-[#7:12]-[C:13] | 104.9 | [{"value": 70.0, "product": "C(C)(C)(C)OC(N[C@@H](CC(C)C)C(N[C@@H]1[C@@H](C(N[C@@H](CC1)C)S(=O)(=O)C1=NC=CC=C1)O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 104.9, "product": "C(C)(C)(C)OC(N[C@@H](CC(C)C)C(N[C@@H]1[C@@H](C(N[C@@H](CC1)C)S(=O)(=O)C1=NC=CC=C1)O)=O)=O", "details": "CALCULATEDPERCENT... | null | null | 30 | MINUTE | 2-Pyridine sulfonyl chloride (0.71 g, 0.4 mmol) was added to a solution of [(S)-1-((3S,4S,7R)-3-Hydroxy-7-methyl-azepan-4-ylcarbamoyl)-3-methyl-butyl]-carbamic acid tert-butyl ester (0.126 g, 0.344 mmol), sodium bicarbonate (0.87 g, 1.03 mmol) in CH2Cl2 (3 ml) and H2O (2 ml) and was stirred at RT for 30 minutes. The re... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Sulfone | C1CCCNCC1 | C1CCCNCC1 | C1CCCNCC1.c1ccncc1 | HCl | O.C(Cl)Cl.CCOC(=O)C | null | 0.5 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NC[C@@H]1O.O=S(=O)(Cl)c1ccccn1>O.C(Cl)Cl.CCOC(=O)C>CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NC(S(=O)(=O)c2ccccn2)[C@H]1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cb7ae3420b1542f3a6e98d11403f3c91 | CC(C)C[C@H](NC(=O)c1cc2ncccc2o1)C(=O)N[C@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)C[C@@H]1O>>CC(C)C[C@H](NC(=O)c1cc2ncccc2o1)C(=O)N[C@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)CC1=O | C(C)N(CC)CC.O[C@H]1CN([C@@H](CC[C@@H]1NC(=O)[C@H](CC(C)C)NC(=O)C1=CC2=NC=CC=C2O1)C)S(=O)(=O)C1=NC=CC=C1.C(C)N(CC)CC>>CC(C[C@@H](C(N[C@@H]1C(CN([C@@H](CC1)C)S(=O)(=O)C1=NC=CC=C1)=O)=O)NC(=O)C1=CC2=NC=CC=C2O1)C | [CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH:6][C:7](=[O:8])[c:9]1[cH:10][c:11]2[n:12][cH:13][cH:14][cH:15][c:16]2[o:17]1)[C:18](=[O:19])[NH:20][C@H:21]1[CH2:22][CH2:23][C@@H:24]([CH3:25])[N:26]([S:27](=[O:28])(=[O:29])[c:30]2[cH:31][cH:32][cH:33][cH:34][n:35]2)[CH2:36][C@@H:37]1[OH:38]>>[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5... | CC(C)C[C@H](NC(=O)c1cc2ncccc2o1)C(=O)N[C@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)C[C@@H]1O | CC(C)C[C@H](NC(=O)c1cc2ncccc2o1)C(=O)N[C@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)CC1=O | null | null | O.CS(=O)C | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 14b488e4129d7de2d07ca6b39e641a5c8222ffe6452ab415aeabbdbcc777a2ba | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C(CNC(=O)c1cc2ncccc2o1)N[C@H]1CCCN(S(=O)(=O)c2ccccn2)CC1=O | [#16:1]-[#7:2](-[C:3])-[C:4]-[C@H;D3;+0:5](-[OH;D1;+0:6])-[C:7](-[#7:8]-[C:9]=[O;D1;H0:10])-[C:11]>>[#16:1]-[#7:2](-[C:3])-[C:4]-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-[C:7](-[#7:8]-[C:9]=[O;D1;H0:10])-[C:11] | 22.4 | [{"value": 22.0, "product": "CC(C[C@@H](C(N[C@@H]1C(CN([C@@H](CC1)C)S(=O)(=O)C1=NC=CC=C1)=O)=O)NC(=O)C1=CC2=NC=CC=C2O1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 22.4, "product": "CC(C[C@@H](C(N[C@@H]1C(CN([C@@H](CC1)C)S(=O)(=O)C1=NC=CC=C1)=O)=O)NC(=O)C1=CC2=NC=CC=C2O1)C", "details": "CALCULATEDPERC... | null | null | 1 | HOUR | Sulfur trioxide-pyridine complex (0.050 g, 0.31 mmol) was added to a solution of Furo[3,2-b]pyridine-2-carboxylic acid {(S)-1-[(3S,4S,7R)-3-hydroxy-7-methyl-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-3-methyl-butyl}-amide (0.056 g, 0.103 mmol) in DMSO (1.0 ml) and triethylamine (0.085 ml, 0.6 mmol) was stirred at RT... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | C1CCC[NH]CC1 | C1CCC[NH]CC1 | c1cnc2ccoc2c1.C1CCC[NH]CC1.c1ccncc1 | null | O.CS(=O)C | null | 1 | CC(C)C[C@H](NC(=O)c1cc2ncccc2o1)C(=O)N[C@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)C[C@@H]1O>O.CS(=O)C>CC(C)C[C@H](NC(=O)c1cc2ncccc2o1)C(=O)N[C@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)CC1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-af985fc071a748b8a19e2288eee8badc | C=C[CH2][Mg][Cl].C[C@H](CI)NC(=O)OCc1ccccc1>>C=CCC[C@@H](C)NC(=O)OCc1ccccc1 | C(C=C)[Mg]Cl.C(C1=CC=CC=C1)OC(N[C@@H](CI)C)=O>>C(C1=CC=CC=C1)OC(N[C@@H](CCC=C)C)=O | [Cl][Mg][CH2:3][CH:2]=[CH2:1].I[CH2:4][C@@H:5]([CH3:6])[NH:7][C:8](=[O:9])[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][C@@H:5]([CH3:6])[NH:7][C:8](=[O:9])[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | C=C[CH2][Mg][Cl].C[C@H](CI)NC(=O)OCc1ccccc1 | C=CCC[C@@H](C)NC(=O)OCc1ccccc1 | null | CSC.[Cu]Br | C1CCOC1 | C-C Coupling | OtherReaction | 95388f86cfea993e1d805de665d94c100ee3193d1978ecc8dd5e389bef693379 | d05251cf430cdb8f7fa37cdc312f93d4b47af4d8ed879f979cecc41cba4e1db9 | c1ccccc1 | I-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])-[#7:4]-[C:5]=[O;D1;H0:6].[C;D1;H2:7]=[C:8]-[CH2;D2;+0:9]-[Mg]-[Cl]>>[C;D1;H2:7]=[C:8]-[CH2;D2;+0:9]-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])-[#7:4]-[C:5]=[O;D1;H0:6] | null | [] | -78 | CELSIUS | 30 | MINUTE | Copper (I) bromide-dimethyl sulfide (1.93 g, 9.4 mmol) was dissolved in distilled ThF (24 ml), then was cooled to −78 degrees C. A solution of allyl magnesium chloride (9.4 ml, 2M in THF, Aldrich) was added dropwise, then the solution was stirred for 30 minutes. ((R)-2-Iodo-1-methyl-ethyl)-carbamic acid benzyl ester (1... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Primary halide.Allyl | Allyl | null | null | c1ccccc1 | I-.Mg | CSC.[Cu]Br.C1CCOC1 | -78 | 0.5 | C=C[CH2][Mg][Cl].C[C@H](CI)NC(=O)OCc1ccccc1>CSC.[Cu]Br.C1CCOC1>C=CCC[C@@H](C)NC(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1799ef2764c941be912a15011bf5fd11 | C=CCBr.C=CCC[C@@H](C)NC(=O)OCc1ccccc1>>C=CCC[C@@H](C)N(CC=C)C(=O)OCc1ccccc1 | Cl.[H-].[Na+].C(C1=CC=CC=C1)OC(N[C@@H](CCC=C)C)=O.C(C=C)Br>>C(C1=CC=CC=C1)OC(N([C@@H](CCC=C)C)CC=C)=O | Br[CH2:8][CH:9]=[CH2:10].[CH2:1]=[CH:2][CH2:3][CH2:4][C@@H:5]([CH3:6])[NH:7][C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][C@@H:5]([CH3:6])[N:7]([CH2:8][CH:9]=[CH2:10])[C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | C=CCBr.C=CCC[C@@H](C)NC(=O)OCc1ccccc1 | C=CCC[C@@H](C)N(CC=C)C(=O)OCc1ccccc1 | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 9f7a278cd5a191722d3eecc8371d7231da3fad2a3edd5ef5de754861b04320e0 | 98c73e1c03b612cc551f19f8f11205127745c589dc895b7127fa7c2738e6ad4e | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[NH;D2;+0:8]-[C:9](-[C:10])-[C;D1;H3:11]>>[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3])-[C:9](-[C:10])-[C;D1;H3:11] | 95.3 | [{"value": 95.0, "product": "C(C1=CC=CC=C1)OC(N([C@@H](CCC=C)C)CC=C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.3, "product": "C(C1=CC=CC=C1)OC(N([C@@H](CCC=C)C)CC=C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | ((R)-1-Methyl-pent-4-enyl)-carbamic acid benzyl ester (790 mg, 3.39 mmol) was dissolved in DMF (8 ml) and was cooled to 0 degrees C. Sodium hydride (60% dispersion, 271 mg, 6.78 mmol) was added and the reaction was stirred for 15 minutes. Allyl bromide (1.23 g, 0.88 ml, 10.17 mmol) was added and the reaction mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester | Carbamic ester.Allyl | null | null | c1ccccc1 | HBr | O.CN(C)C=O | 0 | 0.25 | C=CCBr.C=CCC[C@@H](C)NC(=O)OCc1ccccc1>O.CN(C)C=O>C=CCC[C@@H](C)N(CC=C)C(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f183ecfed6a04d0a84ad0f521443a88f | C=CCCC(C)N(CC=C)C(=O)OCc1ccccc1>>CC1CCC=CCN1C(=O)OCc1ccccc1 | C(C1=CC=CC=C1)OC(N(C(CCC=C)C)CC=C)=O>>C(C1=CC=CC=C1)OC(=O)N1C(CCC=CC1)C | C=[CH:5][CH2:4][CH2:3][CH:2]([CH3:1])[N:8]([CH2:7][CH:6]=C)[C:9](=[O:10])[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH:5]=[CH:6][CH2:7][N:8]1[C:9](=[O:10])[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | C=CCCC(C)N(CC=C)C(=O)OCc1ccccc1 | CC1CCC=CCN1C(=O)OCc1ccccc1 | null | C=CC1=CC=CC=C1.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Ru]Cl.C=CC1=CC=CC=C1.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Ru]Cl | C(Cl)Cl | C-C Coupling | OtherReaction | 1c1bcb324a99f1f7cdfad1cda20c60d4247a90d693ba0f29142115753e5db166 | 67a23c4de67c22dcd6bc1d4c033efdcf679af248440c3b10e6768679c5f73280 | O=C(OCc1ccccc1)N1CC=CCCC1 | C=[CH;D2;+0:1]-[C:2]-[#7:3]-[C:4]=[O;D1;H0:5].C=[CH;D2;+0:6]-[C:7]-[C:8]>>[C:8]-[C:7]-[CH;D2;+0:6]=[CH;D2;+0:1]-[C:2]-[#7:3]-[C:4]=[O;D1;H0:5] | 92 | [{"value": 92.0, "product": "C(C1=CC=CC=C1)OC(=O)N1C(CCC=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.0, "product": "C(C1=CC=CC=C1)OC(=O)N1C(CCC=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Allyl-(1-methyl-pent-4-enyl)-carbamic acid benzyl ester (0.872 g, 3.19 mmol) was dissolved in CH2Cl2 (10 ml) and a stream of argon gas was bubbled into the reaction mixture for 10 minutes. Then bis(tricyclohexylphosphine)benzylidine ruthenium(IV) dichloride (Strem Chemicals, Grubbs' catalyst, 19 mg, 0.0227 mmol) was ad... | 10.6084/m9.figshare.5104873.v1 | null | Allyl.Allyl | null | null | C1=CC[NH]CCC1 | C1=CC[NH]CCC1.c1ccccc1 | Other | C=CC1=CC=CC=C1.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Ru]Cl.C=CC1=CC=CC=C1.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Ru]Cl.C(Cl)Cl | null | null | C=CCCC(C)N(CC=C)C(=O)OCc1ccccc1>C=CC1=CC=CC=C1.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Ru]Cl.C=CC1=CC=CC=C1.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Ru]Cl.C(Cl)Cl>CC1CCC=CCN1C(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ba780dc8f8a9432d8c5fa5b1ed4bc72b | CC1CCC=CCN1C(=O)OCc1ccccc1>>C[C@@H]1CC[C@@H]2O[C@H]2CN1C(=O)OCc1ccccc1 | ClC1=CC(=CC=C1)C(=O)OO.C(C1=CC=CC=C1)OC(=O)N1C(CCC=CC1)C.ClC1=CC(=CC=C1)C(=O)OO>>C(C1=CC=CC=C1)OC(=O)N1C[C@@H]2O[C@H]2CC[C@H]1C | [CH3:1][CH:2]1[CH2:3][CH2:4][CH:5]=[CH:7][CH2:8][N:9]1[C:10](=[O:11])[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][C@@H:5]2[O:6][C@H:7]2[CH2:8][N:9]1[C:10](=[O:11])[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | CC1CCC=CCN1C(=O)OCc1ccccc1 | C[C@@H]1CC[C@@H]2O[C@H]2CN1C(=O)OCc1ccccc1 | null | null | C(Cl)Cl | Oxidation | OtherReaction | 7be9fb2eb503562d5ea21c3d097422001c85c0fb3ec6af3510a546b05688164f | 064ea107e05241c09a52d804a18982a555fc0def251e05abc9beed7ecad64b38 | O=C(OCc1ccccc1)N1CCC[C@@H]2O[C@H]2C1 | [#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C:6]-[C:7]-[CH;D2;+0:8]=[CH;D2;+0:9]-[C:10]-1>>[#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C:6]-[C:7]-[C@@H;D3;+0:8]2-[#8:11]-[C@H;D3;+0:9]-2-[C:10]-1 | 75 | [{"value": 75.0, "product": "C(C1=CC=CC=C1)OC(=O)N1C[C@@H]2O[C@H]2CC[C@H]1C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.6, "product": "C(C1=CC=CC=C1)OC(=O)N1C[C@@H]2O[C@H]2CC[C@H]1C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | m-Chloro-perbenzoic acid (1.10 g, 57–86% pure) was added to a solution of 2-methyl-2,3,4,7-tetrahydro-azepine-1-carboxylic acid benzyl ester (0.72 g, 2.94 mmol) in CH2Cl2 at 0 degrees C. The reaction mixture was stirred for half an hour, then was warmed to RT. Additional m-chloro-perbenzoic acid (0.660 g, 57–86% pure) ... | 10.6084/m9.figshare.5104873.v1 | null | null | Ether | C1=CC[NH]CCC1 | C1C[NH]C[C@@H]2O[C@H]2C1 | C1C[NH]C[C@@H]2O[C@H]2C1.c1ccccc1 | Other | C(Cl)Cl | null | null | CC1CCC=CCN1C(=O)OCc1ccccc1>C(Cl)Cl>C[C@@H]1CC[C@@H]2O[C@H]2CN1C(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c5ceefc1d14342279170fb2b446f976a | C[C@@H]1CC[C@H]2O[C@H]2CN1C(=O)OCc1ccccc1.[N-]=[N+]=[N-]>>C[C@@H]1CC[C@H](N=[N+]=[N-])[C@@H](O)CN1C(=O)OCc1ccccc1 | [N-]=[N+]=[N-].[Na+].C(C1=CC=CC=C1)OC(=O)N1C[C@@H]2O[C@@H]2CC[C@H]1C.[Cl-].[NH4+]>>C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@@H]([C@H](C1)O)N=[N+]=[N-])C | [CH3:1][C@@H:2]1[CH2:3][CH2:4][C@@H:5]2[C@@H:9]([O:10]2)[CH2:11][N:12]1[C:13](=[O:14])[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[N-:6]=[N+:7]=[N-:8]>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][C@H:5]([N:6]=[N+:7]=[N-:8])[C@@H:9]([OH:10])[CH2:11][N:12]1[C:13](=[O:14])[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21]... | C[C@@H]1CC[C@H]2O[C@H]2CN1C(=O)OCc1ccccc1.[N-]=[N+]=[N-] | C[C@@H]1CC[C@H](N=[N+]=[N-])[C@@H](O)CN1C(=O)OCc1ccccc1 | null | null | O.CO | Heteroatom Alkylation and Arylation | OtherReaction | 1456e994911707f7df3e98637980691d23a0eb0c7430e6f8999ad88f4b5545a7 | 0de57b50a6157507e9baab9ed62d7e11e29441a6de9ee7172f74a5b142f47048 | O=C(OCc1ccccc1)N1CCCCCC1 | [#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C@@H;D3;+0:6]2-[O;H0;D2;+0:7]-[C@@H;D3;+0:8]-2-[C:9]-[C:10]-[C:11]-1.[N-;H0;D1:12]=[#7;+:13]=[N;-;D1;H0:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C@H;D3;+0:6](-[OH;D1;+0:7])-[C@@H;D3;+0:8](-[N;H0;D2;+0:12]=[#7;+:13]=[N;-;D1;H0:14])-[C:9]-[C:10]-[C:11]-1 | 89 | [{"value": 89.0, "product": "C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@@H]([C@H](C1)O)N=[N+]=[N-])C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.9, "product": "C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@@H]([C@H](C1)O)N=[N+]=[N-])C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Sodium azide (0.139 g, 2.14 mmol) was added to a solution of (1S,4R,7R)-4-methyl-8-oxa-3-aza-bicyclo[5.1.0]octane-3-carboxylic acid benzyl ester (0.186 g, 0.71 mmol) and ammonium chloride (0.114 g, 2.14 mmol) in MeOH (1.5 ml) and H2O (0.15 ml), then was refluxed for 6 h. The reaction mixture was concentrated in vacuo b... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Azide.Secondary alcohol | C1C[NH]C[C@@H]2O[C@@H]2C1 | C1CCC[NH]CC1 | C1CCC[NH]CC1.c1ccccc1 | null | O.CO | null | null | C[C@@H]1CC[C@H]2O[C@H]2CN1C(=O)OCc1ccccc1.[N-]=[N+]=[N-]>O.CO>C[C@@H]1CC[C@H](N=[N+]=[N-])[C@@H](O)CN1C(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-16fdd40419f0425e98a3f5ddf212111d | C[C@@H]1CC[C@H](N=[N+]=[N-])[C@@H](O)CN1C(=O)OCc1ccccc1>>C[C@@H]1CC[C@H](N)[C@@H](O)CN1C(=O)OCc1ccccc1 | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@@H]([C@H](C1)O)N=[N+]=[N-])C>>C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@@H]([C@H](C1)O)N)C | [N-]=[N+]=[N:6][C@H:5]1[CH2:4][CH2:3][C@@H:2]([CH3:1])[N:10]([C:11](=[O:12])[O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:9][C@@H:7]1[OH:8]>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][C@H:5]([NH2:6])[C@@H:7]([OH:8])[CH2:9][N:10]1[C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | C[C@@H]1CC[C@H](N=[N+]=[N-])[C@@H](O)CN1C(=O)OCc1ccccc1 | C[C@@H]1CC[C@H](N)[C@@H](O)CN1C(=O)OCc1ccccc1 | null | null | O.C1(=CC=CC=C1)C.C1CCOC1 | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | O=C(OCc1ccccc1)N1CCCCCC1 | [C:1]-[C:2](-[N;H0;D2;+0:3]=[N+]=[N-])-[C:4]>>[C:1]-[C:2](-[NH2;D1;+0:3])-[C:4] | null | [] | 45 | CELSIUS | null | null | Triphenylphosphine (0.25 g, 0.952 mmol) was added to a solution of (2R,5S,6S)-5-azido-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl ester (0.193 g, 0.635 mmol) in THF (10 ml) and H2O (0.04 ml), then was heated to 45 degrees C. overnight. The reaction mixture was then diluted with toluene (100 ml×2) and was azeotr... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | C1CCC[NH]CC1.c1ccccc1 | Other | O.C1(=CC=CC=C1)C.C1CCOC1 | 45 | null | C[C@@H]1CC[C@H](N=[N+]=[N-])[C@@H](O)CN1C(=O)OCc1ccccc1>O.C1(=CC=CC=C1)C.C1CCOC1>C[C@@H]1CC[C@H](N)[C@@H](O)CN1C(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-229a8bcdcff14392a4a9cbad9b50e5c9 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)O.CC1CCC(N)C(O)CN1C(=O)OCc1ccccc1>>CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)N(C(=O)OCc2ccccc2)C[C@@H]1O | CN(CCCN=C=NCC)C.O.C(=O)(OC(C)(C)C)N[C@@H](CC(C)C)C(=O)O.C(C)(C)N(CC)C(C)C.OC1=CC=CC=2NN=NC21.C(C1=CC=CC=C1)OC(=O)N1C(CCC(C(C1)O)N)C>>C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@@H]([C@H](C1)O)NC([C@H](CC(C)C)NC(=O)OC(C)(C)C)=O)C | O[C:14]([C@H:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:15].[NH2:16][CH:17]1[CH2:18][CH2:19][CH:20]([CH3:21])[N:22]([C:23](=[O:24])[O:25][CH2:26][c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[CH2:33][CH:34]1[OH:35]>>[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH:6][C:7](=[O:... | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)O.CC1CCC(N)C(O)CN1C(=O)OCc1ccccc1 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)N(C(=O)OCc2ccccc2)C[C@@H]1O | null | null | CN(C)C=O.CCOC(=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(OCc1ccccc1)N1CCCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[#8:13]-[C:14](=[O;D1;H0:15])-[#7:16]1-[C:17]-[C:18]-[C:19]-[CH;D3;+0:20](-[NH2;D1;+0:21])-[CH;D3;+0:22](-[O;D1;H1:23])-[C:24]-1>>[#8:13]-[C:14](=[O;D1;H0:15])-[#7:16]1-[C:17]-[C:18]-[C:19]-[C... | 77.8 | [{"value": 72.0, "product": "C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@@H]([C@H](C1)O)NC([C@H](CC(C)C)NC(=O)OC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.8, "product": "C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@@H]([C@H](C1)O)NC([C@H](CC(C)C)NC(=O)OC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "... | null | null | 8 | HOUR | 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide (0.164 g, 0.22 mmol) was added to a solution of Boc-Leucine-hydrate (0.190 g, 0.76 mmol), diisopropylethylamine (0.164 g, 0.22 ml, 1.27 mmol), hydroxybenztriazole (0.114 g, 0.83 mmol), and racemic (2R,5S,6S)-5-Amino-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl ester ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CCC[NH]CC1.c1ccccc1 | HO- | CN(C)C=O.CCOC(=O)C | null | 8 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)O.CC1CCC(N)C(O)CN1C(=O)OCc1ccccc1>CN(C)C=O.CCOC(=O)C>CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)N(C(=O)OCc2ccccc2)C[C@@H]1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4c436168e88246f48c751d9341ec88b5 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)N(C(=O)OCc2ccccc2)C[C@@H]1O>>CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NC[C@@H]1O | C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@@H]([C@H](C1)O)NC([C@H](CC(C)C)NC(=O)OC(C)(C)C)=O)C.CO.[H][H]>>C(C)(C)(C)OC(N[C@@H](CC(C)C)C(N[C@@H]1[C@H](CN[C@@H](CC1)C)O)=O)=O | O=C(OCc1ccccc1)[N:22]1[C@H:20]([CH3:21])[CH2:19][CH2:18][C@H:17]([NH:16][C:14]([C@H:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:15])[C@@H:24]([OH:25])[CH2:23]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[C:14](=[O:... | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)N(C(=O)OCc2ccccc2)C[C@@H]1O | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NC[C@@H]1O | null | [Pd] | CCOC(=O)C | Reduction | Hydrogenolysis of tertiary amines | 4baebb2e24e86e84182af36602f2110147b788036582af3484a3c912f0e742fe | 20c36f41eeb07c3ba4437b51ba72e8ff3c22d0b27e7197b0e9af3127f331149f | C1CCCNCC1 | O=C(-O-C-c1:c:c:c:c:c:1)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4](-[C;D1;H3:5])-[C:6]>>[C:6]-[C:4](-[C;D1;H3:5])-[NH;D2;+0:1]-[C:2]-[C:3] | null | [] | null | null | 8 | HOUR | (2R,5S,6S)-5-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl ester (0.169 g, 0.344 mmol) was dissovled in EtOAc (3 ml), MeOH (1 ml). Then 10% Pd/C (0.183 g, 0.172 mmol) was added and the reaction was stirred overnight under a balloon filled with hydrogen gas.... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Secondary amine | c1ccccc1.C1CCC[NH]CC1 | C1CCCNCC1 | C1CCCNCC1 | HO- | [Pd].CCOC(=O)C | null | 8 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)N(C(=O)OCc2ccccc2)C[C@@H]1O>[Pd].CCOC(=O)C>CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NC[C@@H]1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e2973fcde70246f9a8bee2d61755ad3a | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NC[C@@H]1O.O=S(=O)(Cl)c1ccccn1>>CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NC(S(=O)(=O)c2ccccn2)[C@H]1O | N1=C(C=CC=C1)S(=O)(=O)Cl.C(C)(C)(C)OC(N[C@@H](CC(C)C)C(N[C@@H]1[C@H](CN[C@@H](CC1)C)O)=O)=O.C([O-])(O)=O.[Na+]>>C(C)(C)(C)OC(N[C@@H](CC(C)C)C(N[C@@H]1[C@@H](C(N[C@@H](CC1)C)S(=O)(=O)C1=NC=CC=C1)O)=O)=O | [CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[C:14](=[O:15])[NH:16][C@H:17]1[CH2:18][CH2:19][C@@H:20]([CH3:21])[NH:22][CH2:23][C@@H:33]1[OH:34].Cl[S:24](=[O:25])(=[O:26])[c:27]1[cH:28][cH:29][cH:30][cH:31][n:32]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH:6][C:7](=[O:8]... | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NC[C@@H]1O.O=S(=O)(Cl)c1ccccn1 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NC(S(=O)(=O)c2ccccn2)[C@H]1O | null | null | O.C(Cl)Cl.CCOC(=O)C | Acylation | OtherReaction | 50e15e487d082133a2541b580d202e111d159447d72a96166c5be5a0b31d1f2a | 12e26711b9e38871791ea5f59b3bfb71dff01e8154858e262eb9cd0332ab4fee | O=S(=O)(c1ccccn1)C1CCCCCN1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#7;a:6]:[c:7].[C:8]-[C:9](-[O;D1;H1:10])-[CH2;D2;+0:11]-[#7:12]-[C:13]>>[C:8]-[C:9](-[O;D1;H1:10])-[CH;D3;+0:11](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#7;a:6]:[c:7])-[#7:12]-[C:13] | 104.9 | [{"value": 70.0, "product": "C(C)(C)(C)OC(N[C@@H](CC(C)C)C(N[C@@H]1[C@@H](C(N[C@@H](CC1)C)S(=O)(=O)C1=NC=CC=C1)O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 104.9, "product": "C(C)(C)(C)OC(N[C@@H](CC(C)C)C(N[C@@H]1[C@@H](C(N[C@@H](CC1)C)S(=O)(=O)C1=NC=CC=C1)O)=O)=O", "details": "CALCULATEDPERCENT... | null | null | 30 | MINUTE | Pyridine-2-sulfonyl chloride (0.71 g, 0.4 mmol) was added to a solution of [(S)-1-((3S,4S,7R)-3-Hydroxy-7-methyl-azepan-4-ylcarbamoyl)-3-methyl-butyl]-carbamic acid tert-butyl ester (0.126 g, 0.344 mmol), sodium bicarbonate (0.87 g, 1.03 mmol) in CH2Cl2 (3 ml) and H2O (2 ml) and was stirred at RT for 30 minutes. The re... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Sulfone | C1CCCNCC1 | C1CCCNCC1 | C1CCCNCC1.c1ccncc1 | HCl | O.C(Cl)Cl.CCOC(=O)C | null | 0.5 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NC[C@@H]1O.O=S(=O)(Cl)c1ccccn1>O.C(Cl)Cl.CCOC(=O)C>CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NC(S(=O)(=O)c2ccccn2)[C@H]1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f3aed56474904f15b2a89ffb12cde371 | CC(C)C[C@H](NC(=O)c1ccc2ncccc2c1)C(=O)N[C@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)CC1O>>CC(C)C[C@H](NC(=O)c1ccc2ncccc2c1)C(=O)N[C@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)CC1=O | C(C)N(CC)CC.CC(C[C@@H](C(N[C@@H]1C(CN([C@@H](CC1)C)S(=O)(=O)C1=NC=CC=C1)O)=O)NC(=O)C=1C=C2C=CC=NC2=CC1)C.C(C)N(CC)CC>>CC(C[C@@H](C(N[C@@H]1C(CN([C@@H](CC1)C)S(=O)(=O)C1=NC=CC=C1)=O)=O)NC(=O)C=1C=C2C=CC=NC2=CC1)C | [CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]2[n:13][cH:14][cH:15][cH:16][c:17]2[cH:18]1)[C:19](=[O:20])[NH:21][C@H:22]1[CH2:23][CH2:24][C@@H:25]([CH3:26])[N:27]([S:28](=[O:29])(=[O:30])[c:31]2[cH:32][cH:33][cH:34][cH:35][n:36]2)[CH2:37][CH:38]1[OH:39]>>[CH3:1][CH:2]([CH3:3])[CH2:4]... | CC(C)C[C@H](NC(=O)c1ccc2ncccc2c1)C(=O)N[C@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)CC1O | CC(C)C[C@H](NC(=O)c1ccc2ncccc2c1)C(=O)N[C@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)CC1=O | null | null | O.CS(=O)C | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 14b488e4129d7de2d07ca6b39e641a5c8222ffe6452ab415aeabbdbcc777a2ba | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C(CNC(=O)c1ccc2ncccc2c1)N[C@H]1CCCN(S(=O)(=O)c2ccccn2)CC1=O | [#16:1]-[#7:2](-[C:3])-[C:4]-[CH;D3;+0:5](-[OH;D1;+0:6])-[C:7](-[#7:8]-[C:9]=[O;D1;H0:10])-[C:11]>>[#16:1]-[#7:2](-[C:3])-[C:4]-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-[C:7](-[#7:8]-[C:9]=[O;D1;H0:10])-[C:11] | 77.1 | [{"value": 77.0, "product": "CC(C[C@@H](C(N[C@@H]1C(CN([C@@H](CC1)C)S(=O)(=O)C1=NC=CC=C1)=O)=O)NC(=O)C=1C=C2C=CC=NC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.1, "product": "CC(C[C@@H](C(N[C@@H]1C(CN([C@@H](CC1)C)S(=O)(=O)C1=NC=CC=C1)=O)=O)NC(=O)C=1C=C2C=CC=NC2=CC1)C", "details": "CALCULATED... | null | null | 1 | HOUR | Sulfur trioxide-pyridine complex (11 mg, 0.7 mmol) was added to a solution of quinoline-6-carboxylic acid {(S)-3-methyl-1-[(4S,7R)-7-methyl-3-hydroxy-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-butyl}-amide (130 mg, 0.235 mmol) in DMSO (2.0 ml) and triethylamine (0.2 ml, 1.4 mmol) was stirred at RT for 1 h. The react... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | C1CCC[NH]CC1 | C1CCC[NH]CC1 | c1ccc2ncccc2c1.C1CCC[NH]CC1.c1ccncc1 | null | O.CS(=O)C | null | 1 | CC(C)C[C@H](NC(=O)c1ccc2ncccc2c1)C(=O)N[C@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)CC1O>O.CS(=O)C>CC(C)C[C@H](NC(=O)c1ccc2ncccc2c1)C(=O)N[C@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)CC1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1d155c4ad4fa41e3814756aa377f9a0c | CCCN1C[C@H](O)[C@@H](NC(=O)[C@H](CC2CCCCC2)NC(=O)OC(C)(C)C)CC[C@H]1C>>CCCN1C[C@H](O)[C@@H](NC(=O)[C@@H](N)CC2CCCCC2)CC[C@H]1C | Cl.C(C)(C)(C)OC(N[C@@H](CC1CCCCC1)C(N[C@@H]1[C@H](CN([C@@H](CC1)C)CCC)O)=O)=O>>N[C@H](C(=O)N[C@@H]1[C@H](CN([C@@H](CC1)C)CCC)O)CC1CCCCC1 | CC(C)(C)OC(=O)[NH:13][C@H:12]([C:10]([NH:9][C@@H:8]1[C@@H:6]([OH:7])[CH2:5][N:4]([CH2:3][CH2:2][CH3:1])[C@H:23]([CH3:24])[CH2:22][CH2:21]1)=[O:11])[CH2:14][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1>>[CH3:1][CH2:2][CH2:3][N:4]1[CH2:5][C@H:6]([OH:7])[C@@H:8]([NH:9][C:10](=[O:11])[C@@H:12]([NH2:13])[CH2:14][CH:15]2... | CCCN1C[C@H](O)[C@@H](NC(=O)[C@H](CC2CCCCC2)NC(=O)OC(C)(C)C)CC[C@H]1C | CCCN1C[C@H](O)[C@@H](NC(=O)[C@@H](N)CC2CCCCC2)CC[C@H]1C | null | null | O1CCOCC1.CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C(CCC1CCCCC1)N[C@H]1CCCNCC1 | 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:3]-[C:2](-[NH2;D1;+0:1])-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7] | null | [] | null | null | 2 | HOUR | HCl in dioxane (4.0 M, 15 ml) was added to a stirred solution of [(S)-2-Cyclohexyl-1-((3S,4S,7R)-3-hydroxy-7-methyl-1-propyl-azepan-4-ylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester (1.4 g, 3.0 mmol) in MeOH (5 ml). The reaction mixture was stirred for 2 h at RT, then was concentrated in vacuo by rotary evaporation ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1CCC[NH]CC1.C1CCCCC1 | HO- | O1CCOCC1.CO | null | 2 | CCCN1C[C@H](O)[C@@H](NC(=O)[C@H](CC2CCCCC2)NC(=O)OC(C)(C)C)CC[C@H]1C>O1CCOCC1.CO>CCCN1C[C@H](O)[C@@H](NC(=O)[C@@H](N)CC2CCCCC2)CC[C@H]1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5dea26f40b26475e9d8c43eb640ab1dc | CCCN1C[C@H](O)[C@@H](NC(=O)[C@@H](N)CC2CCCCC2)CC[C@H]1C.O=C(O)c1ccco1>>CCCN1C[C@H](O)[C@@H](NC(=O)[C@H](CC2CCCCC2)NC(=O)c2ccco2)CC[C@H]1C | CN(CCCN=C=NCC)C.O1C(=CC=C1)C(=O)O.N[C@H](C(=O)N[C@@H]1[C@H](CN([C@@H](CC1)C)CCC)O)CC1CCCCC1.CN1CCOCC1.OC1=CC=CC=2NN=NC21>>C1(CCCCC1)C[C@@H](C(N[C@@H]1[C@H](CN([C@@H](CC1)C)CCC)O)=O)NC(=O)C=1OC=CC1 | [CH3:1][CH2:2][CH2:3][N:4]1[CH2:5][C@H:6]([OH:7])[C@@H:8]([NH:9][C:10](=[O:11])[C@H:12]([CH2:13][CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[NH2:20])[CH2:28][CH2:29][C@H:30]1[CH3:31].O[C:21](=[O:22])[c:23]1[cH:24][cH:25][cH:26][o:27]1>>[CH3:1][CH2:2][CH2:3][N:4]1[CH2:5][C@H:6]([OH:7])[C@@H:8]([NH:9][C:10](=[O:11]... | CCCN1C[C@H](O)[C@@H](NC(=O)[C@@H](N)CC2CCCCC2)CC[C@H]1C.O=C(O)c1ccco1 | CCCN1C[C@H](O)[C@@H](NC(=O)[C@H](CC2CCCCC2)NC(=O)c2ccco2)CC[C@H]1C | null | null | CN(C)C=O.CCOC(=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(N[C@@H](CC1CCCCC1)C(=O)N[C@H]1CCCNCC1)c1ccco1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10](=[O;D1;H0:11])-[#7:12]-[C:13]>>[C:7]-[C:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6])-[C:10](=[O;D1;H0:11])-[#7:12]-[C:13] | 76.9 | [{"value": 76.0, "product": "C1(CCCCC1)C[C@@H](C(N[C@@H]1[C@H](CN([C@@H](CC1)C)CCC)O)=O)NC(=O)C=1OC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.9, "product": "C1(CCCCC1)C[C@@H](C(N[C@@H]1[C@H](CN([C@@H](CC1)C)CCC)O)=O)NC(=O)C=1OC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide (0.10 g, 0.53 mmol) was added to a solution of furan-2-carboxylic acid (0.059 g, 0.53 mmol), (S)-2-Amino-3-cyclohexyl-N-((3S,4S,7R)-3-hydroxy-7-methyl-1-propyl-azepan-4-yl)-propionamide (0.15 g, 0.36 mmol), 4-methylmorpholine (0.14 g, 0.16 ml, 1.44 mmol), hydroxybenztriazol... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CCC[NH]CC1.C1CCCCC1.c1ccoc1 | HO- | CN(C)C=O.CCOC(=O)C | null | 8 | CCCN1C[C@H](O)[C@@H](NC(=O)[C@@H](N)CC2CCCCC2)CC[C@H]1C.O=C(O)c1ccco1>CN(C)C=O.CCOC(=O)C>CCCN1C[C@H](O)[C@@H](NC(=O)[C@H](CC2CCCCC2)NC(=O)c2ccco2)CC[C@H]1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-808d165d121346eab84240fc7724fb06 | CCCN1C[C@H](O)[C@@H](NC(=O)[C@H](CC2CCCCC2)NC(=O)c2ccco2)CC[C@H]1C>>CCCN1CC(=O)[C@@H](NC(=O)[C@H](CC2CCCCC2)NC(=O)c2ccco2)CC[C@H]1C | C1(CCCCC1)C[C@@H](C(N[C@@H]1[C@H](CN([C@@H](CC1)C)CCC)O)=O)NC(=O)C=1OC=CC1.C(C)N(CC)CC>>C1(CCCCC1)C[C@@H](C(N[C@@H]1C(CN([C@@H](CC1)C)CCC)=O)=O)NC(=O)C=1OC=CC1 | [CH3:1][CH2:2][CH2:3][N:4]1[CH2:5][C@H:6]([OH:7])[C@@H:8]([NH:9][C:10](=[O:11])[C@H:12]([CH2:13][CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[NH:20][C:21](=[O:22])[c:23]2[cH:24][cH:25][cH:26][o:27]2)[CH2:28][CH2:29][C@H:30]1[CH3:31]>>[CH3:1][CH2:2][CH2:3][N:4]1[CH2:5][C:6](=[O:7])[C@@H:8]([NH:9][C:10](=[O:11])[C@H... | CCCN1C[C@H](O)[C@@H](NC(=O)[C@H](CC2CCCCC2)NC(=O)c2ccco2)CC[C@H]1C | CCCN1CC(=O)[C@@H](NC(=O)[C@H](CC2CCCCC2)NC(=O)c2ccco2)CC[C@H]1C | null | null | O.CS(=O)C | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 14b488e4129d7de2d07ca6b39e641a5c8222ffe6452ab415aeabbdbcc777a2ba | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C(N[C@@H](CC1CCCCC1)C(=O)N[C@H]1CCCNCC1=O)c1ccco1 | [C:1]-[C:2](-[#7:3]-[C:4]=[O;D1;H0:5])-[C@@H;D3;+0:6](-[OH;D1;+0:7])-[C:8]-[#7:9](-[C:10])-[C:11]>>[C:1]-[C:2](-[#7:3]-[C:4]=[O;D1;H0:5])-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[C:8]-[#7:9](-[C:10])-[C:11] | 79 | [{"value": 79.0, "product": "C1(CCCCC1)C[C@@H](C(N[C@@H]1C(CN([C@@H](CC1)C)CCC)=O)=O)NC(=O)C=1OC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 0.1, "product": "C1(CCCCC1)C[C@@H](C(N[C@@H]1C(CN([C@@H](CC1)C)CCC)=O)=O)NC(=O)C=1OC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Sulfur trioxide-pyridine complex (0.0.35 g, 2.2 mmol) was added to a solution of Furan-2-carboxylic acid [(S)-2-cyclohexyl-1-((3S,4S,7R)-3-hydroxy-7-methyl-1-propyl-azepan-4-ylcarbamoyl)-ethyl]-amide (0.19 g, 0.44 mmol) in DMSO (4.0 ml) and triethylamine (0.61 ml, 4.4 mmol) was stirred at RT for 1 h. The reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | C1CCC[NH]CC1 | C1CCC[NH]CC1 | C1CCC[NH]CC1.C1CCCCC1.c1ccoc1 | null | O.CS(=O)C | null | 1 | CCCN1C[C@H](O)[C@@H](NC(=O)[C@H](CC2CCCCC2)NC(=O)c2ccco2)CC[C@H]1C>O.CS(=O)C>CCCN1CC(=O)[C@@H](NC(=O)[C@H](CC2CCCCC2)NC(=O)c2ccco2)CC[C@H]1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9250f4d9bdfb402d8ccd6f88351cf81d | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)N(C(=O)OCc2ccccc2)CC1O>>CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)N(C(=O)OCc2ccccc2)CC1=O | C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@@H](C(C1)O)NC([C@H](CC(C)C)NC(=O)OC(C)(C)C)=O)C.CC(C[C@@H](C(N[C@@H]1C(CN([C@@H](CC1)C)S(=O)(=O)C1=NC=CC=C1)O)=O)NC(=O)C=1C=C2C=CC=NC2=CC1)C>>C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@@H](C(C1)=O)NC([C@H](CC(C)C)NC(=O)OC(C)(C)C)=O)C | [CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[C:14](=[O:15])[NH:16][C@H:17]1[CH2:18][CH2:19][C@@H:20]([CH3:21])[N:22]([C:23](=[O:24])[O:25][CH2:26][c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[CH2:33][CH:34]1[OH:35]>>[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH:6][C:7](=[O:... | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)N(C(=O)OCc2ccccc2)CC1O | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)N(C(=O)OCc2ccccc2)CC1=O | null | null | null | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 14b488e4129d7de2d07ca6b39e641a5c8222ffe6452ab415aeabbdbcc777a2ba | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C1CCCCN(C(=O)OCc2ccccc2)C1 | [#8:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[C:6]-[CH;D3;+0:7](-[OH;D1;+0:8])-[C:9](-[#7:10]-[C:11]=[O;D1;H0:12])-[C:13]>>[#8:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[C:6]-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[C:9](-[#7:10]-[C:11]=[O;D1;H0:12])-[C:13] | null | [] | null | null | null | null | Following the procedure of Example 12 (m), except substituting “(2R,5S)-5-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-2-methyl-6-hydroxy-azepane-1-carboxylic acid benzyl ester” for “quinoline-6-carboxylic acid {(S)-3-methyl-1-[(4S,7R)-7-methyl-3-hydroxy-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-butyl}-... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | C1CCC[NH]CC1 | C1CCC[NH]CC1 | C1CCC[NH]CC1.c1ccccc1 | null | null | null | null | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)N(C(=O)OCc2ccccc2)CC1O>>CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)N(C(=O)OCc2ccccc2)CC1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1dc677dd33f24b8faee15a8e881a3763 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NCC1O.COC(=O)[C@H](CC(C)C)N=C=O>>COC(=O)[C@H](CC(C)C)NC(=O)N1CC(O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)OC(C)(C)C)CC[C@H]1C | C(C)(C)(C)OC(N[C@@H](CC(C)C)C(N[C@@H]1C(CN[C@@H](CC1)C)O)=O)=O.COC([C@H](CC(C)C)N=C=O)=O>>COC([C@H](CC(C)C)NC(=O)N1[C@@H](CC[C@@H](C(C1)O)NC([C@H](CC(C)C)NC(=O)OC(C)(C)C)=O)C)=O | [NH:13]1[CH2:14][CH:15]([OH:16])[C@@H:17]([NH:18][C:19](=[O:20])[C@H:21]([CH2:22][CH:23]([CH3:24])[CH3:25])[NH:26][C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33])[CH2:34][CH2:35][C@H:36]1[CH3:37].[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][CH:7]([CH3:8])[CH3:9])[N:10]=[C:11]=[O:12]>>[CH3:1][O:2][C:3](=[O:4])[C@H:5... | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NCC1O.COC(=O)[C@H](CC(C)C)N=C=O | COC(=O)[C@H](CC(C)C)NC(=O)N1CC(O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)OC(C)(C)C)CC[C@H]1C | null | null | null | Acylation | Urea synthesis via isocyanate and secondary amine | 8075cbe3dd5e59a36e7929b418854fcd8a992efe64f566d6f7cefc83594d3ddf | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | C1CCCNCC1 | [C:1]-[C:2](-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C;D1;H3:9].[C:10]-[C:11]-[NH;D2;+0:12]-[C:13](-[C;D1;H3:14])-[C:15]>>[C:10]-[C:11]-[N;H0;D3;+0:12](-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:3]-[C:2](-[C:1])-[C:6](=[O;D1;H0:7])-[#8:8]-[C;D1;H3:9])-[C:13](-[C;D1;H3:14])-[C:15] | 91.2 | [{"value": 91.0, "product": "COC([C@H](CC(C)C)NC(=O)N1[C@@H](CC[C@@H](C(C1)O)NC([C@H](CC(C)C)NC(=O)OC(C)(C)C)=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.2, "product": "COC([C@H](CC(C)C)NC(=O)N1[C@@H](CC[C@@H](C(C1)O)NC([C@H](CC(C)C)NC(=O)OC(C)(C)C)=O)C)=O", "details": "CALCULATEDPERCENTYIELD... | null | null | 2 | HOUR | [(S)-3-Methyl-1-((4S,7R)-7-methyl-3-hydroxy-azepan-4-ylcarbamoyl)-butyl]-carbamic acid tert-butyl ester (Example 12a–i, 500 mg, 1.4 mmol) was dissolved in TEF (7 ml), then (S)-(−)-2-isocyanato-4-methylvaleric acid methyl ester (180 mg, 1.05 mmol) was added and the reaction mixture was stirred at RT for 2 h. The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CCCNCC1 | C1CCC[NH]CC1 | C1CCC[NH]CC1 | null | null | null | 2 | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H]1CC[C@@H](C)NCC1O.COC(=O)[C@H](CC(C)C)N=C=O>>COC(=O)[C@H](CC(C)C)NC(=O)N1CC(O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)OC(C)(C)C)CC[C@H]1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-093c43d4fa214c23be77efd83b4f641b | COC(=O)[C@H](CC(C)C)NC(=O)N1CC(O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)OC(C)(C)C)CC[C@H]1C>>COC(=O)[C@H](CC(C)C)NC(=O)N1CC(O)[C@@H](NC(=O)[C@@H](N)CC(C)C)CC[C@H]1C | Cl.COC([C@H](CC(C)C)NC(=O)N1[C@@H](CC[C@@H](C(C1)O)NC([C@H](CC(C)C)NC(=O)OC(C)(C)C)=O)C)=O>>COC([C@H](CC(C)C)NC(=O)N1[C@@H](CC[C@@H](C(C1)O)NC([C@H](CC(C)C)N)=O)C)=O | CC(C)(C)OC(=O)[NH:22][C@H:21]([C:19]([NH:18][C@@H:17]1[CH:15]([OH:16])[CH2:14][N:13]([C:11]([NH:10][C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][CH:7]([CH3:8])[CH3:9])=[O:12])[C@H:29]([CH3:30])[CH2:28][CH2:27]1)=[O:20])[CH2:23][CH:24]([CH3:25])[CH3:26]>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][CH:7]([CH3:8])[CH3:9])[NH:10]... | COC(=O)[C@H](CC(C)C)NC(=O)N1CC(O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)OC(C)(C)C)CC[C@H]1C | COC(=O)[C@H](CC(C)C)NC(=O)N1CC(O)[C@@H](NC(=O)[C@@H](N)CC(C)C)CC[C@H]1C | null | null | O1CCOCC1.CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | C1CCCNCC1 | 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:7]-[#7:6]-[C:4](=[O;D1;H0:5])-[C:2](-[C:3])-[NH2;D1;+0:1] | null | [] | null | null | 2.5 | HOUR | 4.0 M HCl in dioxane (8 ml) was added to a stirred solution (S)-2-({1-[(2R,5S)-5-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-2-methyl-6-hydroxy-azepan-1-yl]-methanoyl}-amino)-4-methyl-pentanoic acid methyl ester (490 mg, 0.93 mmol) in MeOH (8 ml). The reaction mixture was stirred for 2.5 h at RT, then was ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1CCC[NH]CC1 | HO- | O1CCOCC1.CO | null | 2.5 | COC(=O)[C@H](CC(C)C)NC(=O)N1CC(O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)OC(C)(C)C)CC[C@H]1C>O1CCOCC1.CO>COC(=O)[C@H](CC(C)C)NC(=O)N1CC(O)[C@@H](NC(=O)[C@@H](N)CC(C)C)CC[C@H]1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-177873ee2f2e4660b192d6dce8351ac0 | COC(=O)[C@H](CC(C)C)NC(=O)N1CC(O)[C@@H](NC(=O)[C@@H](N)CC(C)C)CC[C@H]1C.O=C(O)c1cc2ccccc2o1>>COC(=O)[C@H](CC(C)C)NC(=O)N1C[C@H](O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)c2cc3ccccc3o2)CC[C@H]1C | CN(CCCN=C=NCC)C.O1C(=CC2=C1C=CC=C2)C(=O)O.COC([C@H](CC(C)C)NC(=O)N1[C@@H](CC[C@@H](C(C1)O)NC([C@H](CC(C)C)N)=O)C)=O.C(C)(C)N(CC)C(C)C.OC1=CC=CC=2NN=NC21>>COC([C@H](CC(C)C)NC(=O)N1[C@@H](CC[C@@H]([C@H](C1)O)NC([C@H](CC(C)C)NC(=O)C=1OC2=C(C1)C=CC=C2)=O)C)=O | [CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][CH:7]([CH3:8])[CH3:9])[NH:10][C:11](=[O:12])[N:13]1[CH2:14][CH:15]([OH:16])[C@@H:17]([NH:18][C:19](=[O:20])[C@H:21]([CH2:22][CH:23]([CH3:24])[CH3:25])[NH2:26])[CH2:38][CH2:39][C@H:40]1[CH3:41].O[C:27](=[O:28])[c:29]1[cH:30][c:31]2[cH:32][cH:33][cH:34][cH:35][c:36]2[o:37]1>>[CH3:... | COC(=O)[C@H](CC(C)C)NC(=O)N1CC(O)[C@@H](NC(=O)[C@@H](N)CC(C)C)CC[C@H]1C.O=C(O)c1cc2ccccc2o1 | COC(=O)[C@H](CC(C)C)NC(=O)N1C[C@H](O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)c2cc3ccccc3o2)CC[C@H]1C | null | null | CN(C)C=O.CCOC(=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CNC(=O)c1cc2ccccc2o1)N[C@H]1CCCNCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[C:7]-[#7:8]-[C:9](=[O;D1;H0:10])-[C:11](-[C:12])-[NH2;D1;+0:13]>>[C:7]-[#7:8]-[C:9](=[O;D1;H0:10])-[C:11](-[C:12])-[NH;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6] | 89.7 | [{"value": 84.0, "product": "COC([C@H](CC(C)C)NC(=O)N1[C@@H](CC[C@@H]([C@H](C1)O)NC([C@H](CC(C)C)NC(=O)C=1OC2=C(C1)C=CC=C2)=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.7, "product": "COC([C@H](CC(C)C)NC(=O)N1[C@@H](CC[C@@H]([C@H](C1)O)NC([C@H](CC(C)C)NC(=O)C=1OC2=C(C1)C=CC=C2)=O)C)=O", "detai... | null | null | 8 | HOUR | 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide (214 g, 1.12 mmol) was added to a solution of benzofuran-2-carboxylic acid (166 g, 1.02 mmol), (S)-2-({1-[(2R,5S)-5-((S)-2-Amino-4-methyl-pentanoylamino)-2-methyl-6-hydroxy-azepan-1-yl]-methanoyl}-amino)-4-methyl-pentanoic acid methyl ester (430 mg, 0.93 mmol), diisopropyle... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CCC[NH]CC1.c1ccc2occc2c1 | HO- | CN(C)C=O.CCOC(=O)C | null | 8 | COC(=O)[C@H](CC(C)C)NC(=O)N1CC(O)[C@@H](NC(=O)[C@@H](N)CC(C)C)CC[C@H]1C.O=C(O)c1cc2ccccc2o1>CN(C)C=O.CCOC(=O)C>COC(=O)[C@H](CC(C)C)NC(=O)N1C[C@H](O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)c2cc3ccccc3o2)CC[C@H]1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-84699b9770274b688649385a7f1ece24 | C[C@@H]1CC[C@@H]2O[C@@H]2CN1C(=O)OCc1ccccc1.[N-]=[N+]=[N-]>>C[C@@H]1CC[C@@H](N=[N+]=[N-])[C@H](O)CN1C(=O)OCc1ccccc1 | [N-]=[N+]=[N-].[Na+].C(C1=CC=CC=C1)OC(=O)N1C[C@H]2O[C@H]2CC[C@H]1C.[Cl-].[NH4+]>>C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@H]([C@@H](C1)O)N=[N+]=[N-])C | [CH3:1][C@@H:2]1[CH2:3][CH2:4][C@H:5]2[C@H:9]([O:10]2)[CH2:11][N:12]1[C:13](=[O:14])[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[N-:6]=[N+:7]=[N-:8]>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][C@@H:5]([N:6]=[N+:7]=[N-:8])[C@H:9]([OH:10])[CH2:11][N:12]1[C:13](=[O:14])[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][c... | C[C@@H]1CC[C@@H]2O[C@@H]2CN1C(=O)OCc1ccccc1.[N-]=[N+]=[N-] | C[C@@H]1CC[C@@H](N=[N+]=[N-])[C@H](O)CN1C(=O)OCc1ccccc1 | null | null | O.CO | Heteroatom Alkylation and Arylation | OtherReaction | 8a8d927db5b14eba751dad0e56ac888829aa426cfc2be5eb7371ace0fee58546 | 0de57b50a6157507e9baab9ed62d7e11e29441a6de9ee7172f74a5b142f47048 | O=C(OCc1ccccc1)N1CCCCCC1 | [#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C@H;D3;+0:6]2-[O;H0;D2;+0:7]-[C@H;D3;+0:8]-2-[C:9]-[C:10]-[C:11]-1.[N-;H0;D1:12]=[#7;+:13]=[N;-;D1;H0:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C@@H;D3;+0:6](-[OH;D1;+0:7])-[C@H;D3;+0:8](-[N;H0;D2;+0:12]=[#7;+:13]=[N;-;D1;H0:14])-[C:9]-[C:10]-[C:11]-1 | 63 | [{"value": 63.0, "product": "C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@H]([C@@H](C1)O)N=[N+]=[N-])C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.9, "product": "C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@H]([C@@H](C1)O)N=[N+]=[N-])C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Sodium azide (1.8 g, 27.7 mmol) was added to a (1R,4R,7S)-4-Methyl-8-oxa-3-aza-bicyclo[5.1.0]octane-3-carboxylic acid benzyl ester (2.4 g, 9.2 mmol, Example 1e) and ammonium chloride (1.48 g, 27.7 mmol) in MeOH (16 ml) and H2O (1.6 ml), then was refluxed overnight. The reaction mixture was concentrated in vacuo by rota... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Azide.Secondary alcohol | C1C[NH]C[C@H]2O[C@H]2C1 | C1CCC[NH]CC1 | C1CCC[NH]CC1.c1ccccc1 | null | O.CO | null | null | C[C@@H]1CC[C@@H]2O[C@@H]2CN1C(=O)OCc1ccccc1.[N-]=[N+]=[N-]>O.CO>C[C@@H]1CC[C@@H](N=[N+]=[N-])[C@H](O)CN1C(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b3c022cf7e5243ba8aa68e0d306bc9cb | C[C@@H]1CC[C@@H](N=[N+]=[N-])[C@H](O)CN1C(=O)OCc1ccccc1>>C[C@@H]1CC[C@@H](N)[C@H](O)CN1C(=O)OCc1ccccc1 | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@H]([C@@H](C1)O)N=[N+]=[N-])C>>C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@H]([C@@H](C1)O)N)C | [N-]=[N+]=[N:6][C@@H:5]1[CH2:4][CH2:3][C@@H:2]([CH3:1])[N:10]([C:11](=[O:12])[O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:9][C@H:7]1[OH:8]>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][C@@H:5]([NH2:6])[C@H:7]([OH:8])[CH2:9][N:10]1[C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | C[C@@H]1CC[C@@H](N=[N+]=[N-])[C@H](O)CN1C(=O)OCc1ccccc1 | C[C@@H]1CC[C@@H](N)[C@H](O)CN1C(=O)OCc1ccccc1 | null | null | O.C1(=CC=CC=C1)C.C1CCOC1 | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | O=C(OCc1ccccc1)N1CCCCCC1 | [C:1]-[C:2](-[N;H0;D2;+0:3]=[N+]=[N-])-[C:4]>>[C:1]-[C:2](-[NH2;D1;+0:3])-[C:4] | null | [] | 45 | CELSIUS | null | null | Triphenylphosphine (2.13 g, 8.14 mmol) was added to a solution (2R,5R,6R)-5-Azido-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl ester (1.65 g, 5.43 mmol) in THF (200 ml) and H2O (0.8 ml), then was heated to 45 degrees C. overnight. The reaction mixture was then diluted with toluene (100 ml×2) and was azeotroped i... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | C1CCC[NH]CC1.c1ccccc1 | Other | O.C1(=CC=CC=C1)C.C1CCOC1 | 45 | null | C[C@@H]1CC[C@@H](N=[N+]=[N-])[C@H](O)CN1C(=O)OCc1ccccc1>O.C1(=CC=CC=C1)C.C1CCOC1>C[C@@H]1CC[C@@H](N)[C@H](O)CN1C(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e2a9e706079841fc94b1ab2be57b3067 | C[C@@H]1CC[C@@H](NC(=O)OC(C)(C)C)[C@H](O)CN1C(=O)OCc1ccccc1>>C[C@@H]1CC[C@@H](NC(=O)OC(C)(C)C)[C@H](O)CN1 | C(C1=CC=CC=C1)OC(=O)N1[C@@H](CC[C@H]([C@@H](C1)O)NC(=O)OC(C)(C)C)C>>C(C)(C)(C)OC(N[C@H]1[C@@H](CN[C@@H](CC1)C)O)=O | O=C(OCc1ccccc1)[N:17]1[C@H:2]([CH3:1])[CH2:3][CH2:4][C@@H:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[C@H:14]([OH:15])[CH2:16]1>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][C@@H:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[C@H:14]([OH:15])[CH2:16][NH:17]1 | C[C@@H]1CC[C@@H](NC(=O)OC(C)(C)C)[C@H](O)CN1C(=O)OCc1ccccc1 | C[C@@H]1CC[C@@H](NC(=O)OC(C)(C)C)[C@H](O)CN1 | null | [Pd] | CCOC(=O)C | Reduction | Hydrogenolysis of tertiary amines | 4baebb2e24e86e84182af36602f2110147b788036582af3484a3c912f0e742fe | 20c36f41eeb07c3ba4437b51ba72e8ff3c22d0b27e7197b0e9af3127f331149f | C1CCCNCC1 | O=C(-O-C-c1:c:c:c:c:c:1)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4](-[C;D1;H3:5])-[C:6]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4](-[C;D1;H3:5])-[C:6] | null | [] | null | null | 8 | HOUR | (2R,5R,6R)-5-tert-Butoxycarbonylamino-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl ester (0.9 g, 2.4 mmol) was dissolved in EtOAc (40 ml), then 10% Pd/C (0.45 g) was added and the reaction mixture was degasses by bubbling argon for 5 minutes. Then, the reaction was stirred overnight under a balloon filled with h... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Secondary amine | c1ccccc1.C1CCC[NH]CC1 | C1CCCNCC1 | C1CCCNCC1 | HO- | [Pd].CCOC(=O)C | null | 8 | C[C@@H]1CC[C@@H](NC(=O)OC(C)(C)C)[C@H](O)CN1C(=O)OCc1ccccc1>[Pd].CCOC(=O)C>C[C@@H]1CC[C@@H](NC(=O)OC(C)(C)C)[C@H](O)CN1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7eabce3c0fd649deb1c2ee99f6f93d3e | C[C@@H]1CC[C@@H](NC(=O)OC(C)(C)C)[C@H](O)CN1.O=S(=O)(Cl)c1ccccn1>>C[C@@H]1CC[C@@H](NC(=O)OC(C)(C)C)[C@H](O)CN1S(=O)(=O)c1ccccn1 | N1=C(C=CC=C1)S(=O)(=O)Cl.C(C)(C)(C)OC(N[C@H]1[C@@H](CN[C@@H](CC1)C)O)=O.C([O-])(O)=O.[Na+]>>C(C)(C)(C)OC(N[C@H]1[C@@H](CN([C@@H](CC1)C)S(=O)(=O)C1=NC=CC=C1)O)=O | [CH3:1][C@@H:2]1[CH2:3][CH2:4][C@@H:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[C@H:14]([OH:15])[CH2:16][NH:17]1.Cl[S:18](=[O:19])(=[O:20])[c:21]1[cH:22][cH:23][cH:24][cH:25][n:26]1>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][C@@H:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[C@H:14]([OH:15])[CH... | C[C@@H]1CC[C@@H](NC(=O)OC(C)(C)C)[C@H](O)CN1.O=S(=O)(Cl)c1ccccn1 | C[C@@H]1CC[C@@H](NC(=O)OC(C)(C)C)[C@H](O)CN1S(=O)(=O)c1ccccn1 | null | null | O.C(Cl)Cl.CCOC(=O)C | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | c2204cc88228cdaa7ea3d28bcc48f34d440fd3b399c9f2744d96a102c54beeff | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=S(=O)(c1ccccn1)N1CCCCCC1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#7;a:6]:[c:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11](-[C;D1;H3:12])-[C:13]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#7;a:6]:[c:7])-[C:11](-[C;D1;H3:12])-[C:13] | 65.6 | [{"value": 65.0, "product": "C(C)(C)(C)OC(N[C@H]1[C@@H](CN([C@@H](CC1)C)S(=O)(=O)C1=NC=CC=C1)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.6, "product": "C(C)(C)(C)OC(N[C@H]1[C@@H](CN([C@@H](CC1)C)S(=O)(=O)C1=NC=CC=C1)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Pyridine-2-sulfonyl chloride (0.55 g, 3.1 mmol) was added to a solution ((3R,4R,7R)-3-Hydroxy-7-methyl-azepan-4-yl)-carbamic acid tert-butyl ester (0.58 g, 0.2.4 mmol), sodium bicarbonate (0.84 g, 10 mmol) in CH2Cl2 (10 ml) and H2O (3 ml) and was stirred at RT for 30 minutes. The reaction mixture was diluted with EtOAc... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1CCCNCC1 | C1CCC[NH]CC1 | C1CCC[NH]CC1.c1ccncc1 | HCl | O.C(Cl)Cl.CCOC(=O)C | null | 0.5 | C[C@@H]1CC[C@@H](NC(=O)OC(C)(C)C)[C@H](O)CN1.O=S(=O)(Cl)c1ccccn1>O.C(Cl)Cl.CCOC(=O)C>C[C@@H]1CC[C@@H](NC(=O)OC(C)(C)C)[C@H](O)CN1S(=O)(=O)c1ccccn1 |
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