dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a6a4e383f46e49689e82ca555e0f2d07 | CCOC(=O)CC(=O)OCC.Cc1ccc(CCl)cc1C>>Cc1ccc(CCC(=O)O)cc1C | C(CC(=O)OCC)(=O)OCC.[Na].CC=1C=C(CCl)C=CC1C>>CC=1C=C(C=CC1C)CCC(=O)O | CCOC(=O)[CH2:7][C:8](=[O:9])[O:10]CC.Cl[CH2:6][c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:12]([CH3:13])[cH:11]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][C:8](=[O:9])[OH:10])[cH:11][c:12]1[CH3:13] | CCOC(=O)CC(=O)OCC.Cc1ccc(CCl)cc1C | Cc1ccc(CCC(=O)O)cc1C | null | null | C(C)O.C(C)OCC | C-C Coupling | OtherReaction | 90d818ca224bdabc25e634bb88b5af950c37a4d4619d5c75a3e0b8c845e0c849 | 265ce9ab6ce6788b290bc39b3c46178d8de828f28e70156cf46ae0b38e670684 | c1ccccc1 | C-C-O-C(=O)-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-C-C.Cl-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:4])-[CH2;D2;+0:1]-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8] | 55 | [{"value": 55.0, "product": "CC=1C=C(C=CC1C)CCC(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a solution of 70.0 ml of diethyl malonate dissolved in 400 ml of dry ethanol was added 10.0 g of metalic sodium. The reaction mixture was stirred for 30 minutes and cooled to 0° C; and 66.5 g of 3,4-dimethylbenzyl chloride was added thereto. This reaction mixture was stirred for 1 hour at room temperature, heated at... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester | Carboxylic acid | null | null | c1ccccc1 | HCl | C(C)O.C(C)OCC | 0 | 0.5 | CCOC(=O)CC(=O)OCC.Cc1ccc(CCl)cc1C>C(C)O.C(C)OCC>Cc1ccc(CCC(=O)O)cc1C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-624baddf6e7e48f1aa989e032d3a290c | Cc1ccc(CCl)cc1C.[C-]#N>>Cc1ccc(CC#N)cc1C | [C-]#N.[Na+].CC=1C=C(CCl)C=CC1C>>CC=1C=C(CC#N)C=CC1C | Cl[CH2:6][c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:10]([CH3:11])[cH:9]1.[C-:7]#[N:8]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][C:7]#[N:8])[cH:9][c:10]1[CH3:11] | Cc1ccc(CCl)cc1C.[C-]#N | Cc1ccc(CC#N)cc1C | null | null | C(C)O.O | C-C Coupling | OtherReaction | 347b040e695b34bb71d78d55beea9c7162795a061d052426f1f803b52c4cbe4d | 1dbefa1fc17e03074aa3f6619987f71dfa9a1cb0d61de142a880cd3f05e4f004 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C-;H0;D1:5]#[N;D1;H0:6]>>[N;D1;H0:6]#[C;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 79 | [{"value": 79.0, "product": "CC=1C=C(CC#N)C=CC1C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.0, "product": "CC=1C=C(CC#N)C=CC1C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 6.8 g of 90% sodium cyanide dissolved in 6.5 ml of distilled water while being subjected to heating was added a solution of 15.5 g of 3,4-dimethylbenzyl chloride in 20 ml of dry ethanol; and the resultant mixture was heated at the boiling temperature for 10 hours and then cooled to room temperature. Th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Nitrile | null | null | c1ccccc1 | Other | C(C)O.O | null | null | Cc1ccc(CCl)cc1C.[C-]#N>C(C)O.O>Cc1ccc(CC#N)cc1C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-161f70f75d474c90b1197e7470e29948 | O=C(O)C=Cc1ccc(Cl)cc1>>O=C(O)CCc1ccc(Cl)cc1 | ClC1=CC=C(C=CC(=O)O)C=C1.NN>>ClC1=CC=C(C=C1)CCC(=O)O | [O:1]=[C:2]([OH:3])[CH:4]=[CH:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1 | O=C(O)C=Cc1ccc(Cl)cc1 | O=C(O)CCc1ccc(Cl)cc1 | null | null | C(C)O | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccccc1 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[CH;D2;+0:4]=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8] | 89 | [{"value": 89.0, "product": "ClC1=CC=C(C=C1)CCC(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.7, "product": "ClC1=CC=C(C=C1)CCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | A mixture of 6.75 g of 4-chlorocinnamic acid and 0.3 g of CuSO4.5H2O dispersed in 50 ml of ethyl alcohol was stirred at room temperature for 10 minutes; and 23 ml of 95% hydrazine was added thereto. This reactant was stirred for 18 hours with air bubbling at the speed of 1 L/min. The reaction mixture was filtered throu... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | C(C)O | null | 0.166667 | O=C(O)C=Cc1ccc(Cl)cc1>C(C)O>O=C(O)CCc1ccc(Cl)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-cba18c7783e64b07b2d8f20d24a2f6f6 | O=C(O)C=Cc1ccc2c(c1)OCO2>>O=C(O)CCc1ccc2c(c1)OCO2 | C1OC=2C=C(C=CC(=O)O)C=CC2O1.O.[H][H]>>C1OC=2C=C(C=CC2O1)CCC(=O)O | [O:1]=[C:2]([OH:3])[CH:4]=[CH:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[O:12][CH2:13][O:14]2>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[O:12][CH2:13][O:14]2 | O=C(O)C=Cc1ccc2c(c1)OCO2 | O=C(O)CCc1ccc2c(c1)OCO2 | null | [Pd] | [OH-].[Na+] | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc2c(c1)OCO2 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[CH;D2;+0:4]=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8] | 97 | [{"value": 97.0, "product": "C1OC=2C=C(C=CC2O1)CCC(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.0, "product": "C1OC=2C=C(C=CC2O1)CCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 10.0 g of 3,4-methylenedioxycinnamic acid dissolved in 130 ml of 10% NaOH and 80 ml of distilled water was added 1.0 g of 5% Pd-C. This mixture was reacted at 40 psi until the consumption of hydrogen gas was ceased and then filtered through a Celite layer. The filtrate was acidified with concentrated h... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2c(c1)OCO2 | null | [Pd].[OH-].[Na+] | null | null | O=C(O)C=Cc1ccc2c(c1)OCO2>[Pd].[OH-].[Na+]>O=C(O)CCc1ccc2c(c1)OCO2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-34fa8b341ee347298276cad877914064 | NC(=O)CCc1ccc2c(c1)OCO2>>NCCCc1ccc2c(c1)OCO2 | C1OC=2C=C(C=CC2O1)CCC(=O)N.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>>C1OC=2C=C(C=CC2O1)CCCN | O=[C:2]([NH2:1])[CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[O:11][CH2:12][O:13]2>>[NH2:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[O:11][CH2:12][O:13]2 | NC(=O)CCc1ccc2c(c1)OCO2 | NCCCc1ccc2c(c1)OCO2 | null | null | O.O1CCCC1 | Reduction | Reduction of primary amides to amines | 71f4ab6e4ff9fd6ad8fb6a6879cdc6c258d35bb85b9b40ad2783b874bf909ba4 | 8776a0c3e2f32dafe87200a597cd55df0b01414bf133bdc9f8f7e1171014bfad | c1ccc2c(c1)OCO2 | O=[C;H0;D3;+0:1](-[N;D1;H2:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:1]-[N;D1;H2:2] | 85 | [{"value": 85.0, "product": "C1OC=2C=C(C=CC2O1)CCCN", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.6, "product": "C1OC=2C=C(C=CC2O1)CCCN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 6.0 g of the above amide was dissolved in 100 ml of dry tetrahydrofuran, which was added dropwise to a suspension of 2.4 g of LiAlH4 in 150 ml of dry tetrahydrofuran. The reaction mixture was refluxed for 2 hours and 10 ml of 1N NaOH was added thereto. The mixture was filtered through a Celite layer to give solids, whi... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide | null | null | null | c1ccc2c(c1)OCO2 | Other | O.O1CCCC1 | null | null | NC(=O)CCc1ccc2c(c1)OCO2>O.O1CCCC1>NCCCc1ccc2c(c1)OCO2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-603826e869b34924b60f03525d155479 | C=CC(=O)OCC.Cc1cccc(CCl)c1>>CCOC(=O)CCCc1cccc(C)c1 | CC=1C=C(CCl)C=CC1.C(C=C)(=O)OCC.C(CCC)[SnH](CCCC)CCCC>>C(C)OC(CCCC1=CC(=CC=C1)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH2:7].Cl[CH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]([CH3:14])[cH:15]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]([CH3:14])[cH:15]1 | C=CC(=O)OCC.Cc1cccc(CCl)c1 | CCOC(=O)CCCc1cccc(C)c1 | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | f7c8844f4eea55ca58f8c1c92b7a422bda06d2bc5f87645d975b8be4949c6e4e | a69f246258a922bf718e25354e9414adb79920a4aa5db361bf2c4794e09e18d2 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH;D2;+0:9]=[CH2;D1;+0:10]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 110 | CELSIUS | null | null | A mixture of 14.0 g of 3-methylbenzyl chloride and 50.0 g of ethyl acrylate dissolved in 300 ml of dry toluene was heated to 110° C. Separatively, 3.0 g of 2,2'-azobisisobutyronitrile(AIBN) and 32.0 g of tri-n-butyltin hydride were dissolved in 200 ml of dry toluene, which was added to the above mixture over a period o... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Vinyl | Ester | null | null | c1ccccc1 | Other | C1(=CC=CC=C1)C | 110 | null | C=CC(=O)OCC.Cc1cccc(CCl)c1>C1(=CC=CC=C1)C>CCOC(=O)CCCc1cccc(C)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-102bee15751b4b71bb53e4792a6e7427 | BrCc1ccccc1.CCOC(=O)Cc1ccc(O)c(O)c1>>CCOC(=O)Cc1ccc(O)c(OCc2ccccc2)c1 | Cl.C([O-])([O-])=O.[K+].[K+].C(C1=CC=CC=C1)Br.C(C)OC(CC1=CC(=C(C=C1)O)O)=O>>C(C)OC(CC1=CC(=C(C=C1)O)OCC1=CC=CC=C1)=O | Br[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]([OH:11])[c:12]([OH:13])[cH:21]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][c:10]([OH:11])[c:12]([O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21]1 | BrCc1ccccc1.CCOC(=O)Cc1ccc(O)c(O)c1 | CCOC(=O)Cc1ccc(O)c(OCc2ccccc2)c1 | null | null | O.CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | 45 | [{"value": 45.0, "product": "C(C)OC(CC1=CC(=C(C=C1)O)OCC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5.79 g of 3,4-dihydroxylphenyl acetic acid ethyl ester dissolved in dry acetone were added 4.48 g of potassium carbonate and 4.15 ml of benzyl bromide. The mixture was heated to reflux until the starting materials were exhausted; and then the solvent was distilled off under reduced pressure. To the res... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | O.CC(=O)C | null | null | BrCc1ccccc1.CCOC(=O)Cc1ccc(O)c(O)c1>O.CC(=O)C>CCOC(=O)Cc1ccc(O)c(OCc2ccccc2)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b4cfc43b497244389389a726047b0d23 | CCOC(=O)Cc1ccc(O)c(OCc2ccccc2)c1>>O=C(O)Cc1ccc(O)c(OCc2ccccc2)c1 | Cl.[OH-].[Na+].C(C)OC(CC1=CC(=C(C=C1)O)OCC1=CC=CC=C1)=O>>C(C1=CC=CC=C1)OC=1C=C(C=CC1O)CC(=O)O | CC[O:3][C:2](=[O:1])[CH2:4][c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19]1>>[O:1]=[C:2]([OH:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19]1 | CCOC(=O)Cc1ccc(O)c(OCc2ccccc2)c1 | O=C(O)Cc1ccc(O)c(OCc2ccccc2)c1 | null | null | O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(COc2ccccc2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 89 | [{"value": 89.0, "product": "C(C1=CC=CC=C1)OC=1C=C(C=CC1O)CC(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.5, "product": "C(C1=CC=CC=C1)OC=1C=C(C=CC1O)CC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5.35 g of the ester obtained above was added to a mixture of 50 ml of water and 1.49 g of sodium hydroxide. The resultant solution was refluxed for 2.5 hours, acidified with concentrated hydrochloric acid and evaporated under reduced pressure to give solids, which were purified by Soxhlet extraction apparatus to provid... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | O | null | null | CCOC(=O)Cc1ccc(O)c(OCc2ccccc2)c1>O>O=C(O)Cc1ccc(O)c(OCc2ccccc2)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f3c48c143b2340d1b98ea10ccaec69eb | CC1(C)CCCC(N)C1.N#C[S-]>>CC1(C)CCCC(NC(N)=S)C1 | C(C1=CC=CC=C1)(=O)Cl.[S-]C#N.[NH4+].CC1(CC(CCC1)N)C>>CC1(CC(CCC1)NC(=S)N)C | [CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][CH2:6][CH:7]([NH2:8])[CH2:12]1.[C:9](#[N:10])[S-:11]>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][CH2:6][CH:7]([NH:8][C:9]([NH2:10])=[S:11])[CH2:12]1 | CC1(C)CCCC(N)C1.N#C[S-] | CC1(C)CCCC(NC(N)=S)C1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 42eba0434e01c5077fe474f99d70dfa303f7fb16e20dbd38eacfbefa3576aa9e | 5d425eb1cdcb05eaa7642d1bd0c9c22fd483e30b54ceb4617e277bc1fc89be52 | C1CCCCC1 | [C:1]-[C:2](-[NH2;D1;+0:3])-[C:4].[N;H0;D1;+0:5]#[C;H0;D2;+0:6]-[S-;H0;D1:7]>>[C:1]-[C:2](-[NH;D2;+0:3]-[C;H0;D3;+0:6](-[NH2;D1;+0:5])=[S;H0;D1;+0:7])-[C:4] | null | [] | null | null | null | null | 59 g (0.42 mol) of benzoyl chloride were added dropwise over the course of 10 minutes to a solution of 33 g (0.44 mol) of ammonium thiocyanate in 100 ml of absolute acetone. The mixture was refluxed for 10 minutes and then 50.8 g (0.40 mol) of 3,3-dimethylcyclohexylamine were added dropwise, and the mixture was refluxe... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Thiourea | null | null | C1CCCCC1 | null | CC(=O)C | null | null | CC1(C)CCCC(N)C1.N#C[S-]>CC(=O)C>CC1(C)CCCC(NC(N)=S)C1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4bb73f6b08114a6bb1231cd70986f4d3 | CO.N=C(N)N(CCCCCCCCNCCCCCCCCC1CCCCC1)C1CCCCC1.O>>CC(=O)O.CC(=O)O.CC(=O)O.N=C(N)N(CCCCCCCCNCCCCCCCCC1CCCCC1)C1CCCCC1 | I.I.C1(CCCCC1)N(C(=N)N)CCCCCCCCNCCCCCCCCC1CCCCC1.CO.O>>C(C)(=O)O.C(C)(=O)O.C(C)(=O)O.C1(CCCCC1)N(C(=N)N)CCCCCCCCNCCCCCCCCC1CCCCC1 | [CH3:2][OH:4].[CH2:1]1[CH2:35][CH:34]([CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][NH:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][N:16]([C:14](=[NH:13])[NH2:15])[CH:40]2[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]2)[CH2:39][CH2:38][CH2:37]1.[OH2:3]>>[CH3:1][C:2](=[O:3])[OH:4].[CH... | CO.N=C(N)N(CCCCCCCCNCCCCCCCCC1CCCCC1)C1CCCCC1.O | CC(=O)O.CC(=O)O.CC(=O)O.N=C(N)N(CCCCCCCCNCCCCCCCCC1CCCCC1)C1CCCCC1 | null | null | null | Acylation | OtherReaction | 4ae6073306b5a63b925338d1011a31b474811a49f807e76a33e47716bdd932fa | bd44f4ff7f0ac10f22254331727f0bdd25b78f70cdf361d5c81ca0e535326223 | C(CCCCNC1CCCCC1)CCCNCCCCCCCCC1CCCCC1 | [CH3;D1;+0:1]-[O;D1;H1:2].[C:3]-[C:4]1-[C:5]-[C:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-1.[OH2;D0;+0:10]>>[CH3;D1;+0:8]-[C;H0;D3;+0:1](-[O;D1;H1:2])=[O;H0;D1;+0:10].[C:3]-[C:4]1-[C:5]-[C:6]-[CH2;D2;+0:7]-[C:11]-[CH2;D2;+0:9]-1 | null | [] | null | null | null | null | 10.2 g (0.011 mol) of 1,17-biscyclohexylguanidino-9-azaheptadecane dihydroiodide in 150 ml of methanol/water (1:1) were filtered through a column containing 250 g of ion exchanger (OH- form). The free guanidine base obtained after working up was dissolved in methanol and converted into the triacetate with excess glacia... | 10.6084/m9.figshare.5104873.v1 | null | Methanol | Carboxylic acid.Carboxylic acid.Carboxylic acid | C1CCCCC1 | C1CCCCC1 | C1CCCCC1.C1CCCCC1 | Other | null | null | null | CO.N=C(N)N(CCCCCCCCNCCCCCCCCC1CCCCC1)C1CCCCC1.O>>CC(=O)O.CC(=O)O.CC(=O)O.N=C(N)N(CCCCCCCCNCCCCCCCCC1CCCCC1)C1CCCCC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-af00d71710294ebab64f63f60bd2b0e6 | N#C[S-].NC1CCCCC1>>NC(=S)NC1CCCCC1 | C(C1=CC=CC=C1)(=O)Cl.[S-]C#N.[NH4+].C1(CCCCC1)N>>C1(CCCCC1)NC(=S)N | [N:1]#[C:2][S-:3].[NH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1>>[NH2:1][C:2](=[S:3])[NH:4][CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1 | N#C[S-].NC1CCCCC1 | NC(=S)NC1CCCCC1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 42eba0434e01c5077fe474f99d70dfa303f7fb16e20dbd38eacfbefa3576aa9e | 5d425eb1cdcb05eaa7642d1bd0c9c22fd483e30b54ceb4617e277bc1fc89be52 | C1CCCCC1 | [C:1]-[C:2](-[NH2;D1;+0:3])-[C:4].[N;H0;D1;+0:5]#[C;H0;D2;+0:6]-[S-;H0;D1:7]>>[C:1]-[C:2](-[NH;D2;+0:3]-[C;H0;D3;+0:6](-[NH2;D1;+0:5])=[S;H0;D1;+0:7])-[C:4] | null | [] | null | null | null | null | 295.5 g (2.1 mol) of benzoyl chloride were added dropwise over the course of 10 minutes to a solution of 165.0 g (2.2 mol) of ammonium thiocyanate in 500 ml of absolute acetone. After refluxing for 10 minutes, 198.9 g (2.0 mol) of cyclohexylamine were added dropwise, and the mixture was refluxed for a further 20 minute... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Thiourea | null | null | C1CCCCC1 | null | CC(=O)C | null | null | N#C[S-].NC1CCCCC1>CC(=O)C>NC(=S)NC1CCCCC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-62caf7e77d574b0eacf847ea9cbf3833 | CO.NC1=NCCCN1CCCCCCCCCCCCN1CCCN=C1N.O>>CC(=O)O.CC(=O)O.NC1=NCCCN1CCCCCCCCCCCCN1CCCN=C1N | I.I.NC1=NCCCN1CCCCCCCCCCCCN1C(=NCCC1)N.CO.O>>C(C)(=O)O.C(C)(=O)O.NC1=NCCCN1CCCCCCCCCCCCN1C(=NCCC1)N | [CH3:2][OH:4].[CH2:1]([CH2:19][CH2:18][CH2:17][CH2:16][N:15]1[C:10]([NH2:9])=[N:11][CH2:12][CH2:13][CH2:14]1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][N:28]1[CH2:29][CH2:30][CH2:31][N:32]=[C:33]1[NH2:34].[OH2:3]>>[CH3:1][C:2](=[O:3])[OH:4].[CH3:5][C:6](=[O:7])[OH:8].[NH2:9][C:10]1=[N:11][CH2:12][CH2:13][... | CO.NC1=NCCCN1CCCCCCCCCCCCN1CCCN=C1N.O | CC(=O)O.CC(=O)O.NC1=NCCCN1CCCCCCCCCCCCN1CCCN=C1N | null | null | null | Acylation | OtherReaction | 869efd95719ef6cb1cfe90947bdd0662dec50621960aff0fd34fba411619ccf2 | fba866f7a3d4b5bb2dceaeeae713f82e77bdf1513de887ed47ead3b7b2e7d1d1 | C1=NCCCN1CCCCCCCCCCCCN1C=NCCC1 | [CH3;D1;+0:1]-[O;D1;H1:2].[C:3]-[C:4]-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[C:8]-[C:9].[OH2;D0;+0:10]>>[CH3;D1;+0:6]-[C;H0;D3;+0:1](-[O;D1;H1:2])=[O;H0;D1;+0:10].[C:3]-[C:4]-[CH2;D2;+0:5]-[C:11]-[CH2;D2;+0:7]-[C:8]-[C:9] | null | [] | null | null | null | null | 30.0 g (0.048 mol) of 1,12-bis(2-amino-3,4,5,6-tetrahydropyrimidyl)dodecane dihydroiodide in 300 ml of methanol/water (1:1) were filtered through a column containing 250 g of ion exchanger (OH- form). The free guanidine base obtained after working up was dissolved in methanol and converted into the diacetate with exces... | 10.6084/m9.figshare.5104873.v1 | null | Methanol | Carboxylic acid.Carboxylic acid | null | null | C1=NCCC[NH]1.C1=NCCC[NH]1 | Other | null | null | null | CO.NC1=NCCCN1CCCCCCCCCCCCN1CCCN=C1N.O>>CC(=O)O.CC(=O)O.NC1=NCCCN1CCCCCCCCCCCCN1CCCN=C1N |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-20f081f30912431cb2a2d521916bd8a4 | C#CCO.C(CCOCC1CO1)COCC1CO1>>C#CCOCC(O)COCCCCOCC(O)COCC#C | C(C1CO1)OCCCCOCC1CO1.C(C#C)O>>C(C#C)OCC(COCCCCOCC(COCC#C)O)O | [CH:1]#[C:2][CH2:3][OH:4].[CH2:5]1[CH:6]([CH2:20][O:19][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH2:15][CH:16]2[O:17][CH2:18]2)[O:7]1>>[CH:1]#[C:2][CH2:3][O:4][CH2:5][CH:6]([OH:7])[CH2:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH2:15][CH:16]([OH:17])[CH2:18][O:19][CH2:20][C:21]#[CH:22] | C#CCO.C(CCOCC1CO1)COCC1CO1 | C#CCOCC(O)COCCCCOCC(O)COCC#C | null | null | null | Functional Group Addition | OtherReaction | 262176ffdb0ebe6f8d6014f595e74e2fefec76f7c9a75e157ff37caf5412ad4e | 899396db132ea97bfe4932cf1ec02adc46159f497988d3dc8ea2d04aed6fd13a | null | [C;D1;H1:1]#[C:2]-[C:3]-[OH;D1;+0:4].[C:5]-[C:6]-[CH2;D2;+0:7]-[O;H0;D2;+0:8]-[CH2;D2;+0:9]-[CH;D3;+0:10]1-[CH2;D2;+0:11]-[O;H0;D2;+0:12]-1.[C:13]-[C:14]1-[CH2;D2;+0:15]-[O;H0;D2;+0:16]-1>>[C:13]-[C:14](-[OH;D1;+0:16])-[CH2;D2;+0:15]-[O;H0;D2;+0:8]-[CH2;D2;+0:9]-[C:17]#[C;D1;H1:18].[C:5]-[C:6]-[CH2;D2;+0:7]-[#8:19]-[C:... | null | [] | null | null | null | null | Analogous to Example 1, 475 g 1,4-diglycidyloxybutane was reacted with 528 g of propargyl alcohol to give 1,4-bis(3-propargyloxy-2-hydroxypropyl) oxybutane.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Primary alcohol | Ether.Ether.Ether.Secondary alcohol.Secondary alcohol.Alkyne | C1CO1.C1CO1 | null | null | Other | null | null | null | C#CCO.C(CCOCC1CO1)COCC1CO1>>C#CCOCC(O)COCCCCOCC(O)COCC#C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-af4c10d538844fb08c46cdd882fe2355 | CCOC(=O)c1ccc2c(c1)C(NCc1cccnc1)c1ccccc1CO2>>O=C(O)c1ccc2c(c1)C(NCc1cccnc1)c1ccccc1CO2 | N1=CC(=CC=C1)CNC1C2=C(OCC3=C1C=CC=C3)C=CC(=C2)C(=O)OCC.CO.[OH-].[Na+]>>N1=CC(=CC=C1)CNC1C2=C(OCC3=C1C=CC=C3)C=CC(=C2)C(=O)O | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[CH:10]([NH:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][n:17][cH:18]1)[c:19]1[cH:20][cH:21][cH:22][cH:23][c:24]1[CH2:25][O:26]2>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[CH:10]([NH:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][n:17][cH:18]1)[c:19]1[cH:20]... | CCOC(=O)c1ccc2c(c1)C(NCc1cccnc1)c1ccccc1CO2 | O=C(O)c1ccc2c(c1)C(NCc1cccnc1)c1ccccc1CO2 | null | null | O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1cncc(CNC2c3ccccc3COc3ccccc32)c1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | Compound 9a, 3.9 g, obtained in Example 1 was heated to reflux for an hour in a solvent mixture of 200 ml of methanol, 50 ml of water and 10 ml of 10N sodium hydroxide aqueous solution. The solvent was distilled off under reduced pressure and 4N hydrochloric acid aqueous solution was added to the residue to adjust pH t... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1.c1ccc2c(c1)COc1ccccc1C2 | Other | O | null | null | CCOC(=O)c1ccc2c(c1)C(NCc1cccnc1)c1ccccc1CO2>O>O=C(O)c1ccc2c(c1)C(NCc1cccnc1)c1ccccc1CO2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-72dde571cee54edf952910d38979812d | COC(=O)c1ccc2c(c1)/C(=C/CCl)c1ccccc1CO2.O=[N+]([O-])c1ccc2nc[nH]c2c1>>COC(=O)c1ccc2c(c1)/C(=C/Cn1cnc3cc([N+](=O)[O-])ccc31)c1ccccc1CO2.COC(=O)c1ccc2c(c1)/C(=C/Cn1cnc3ccc([N+](=O)[O-])cc31)c1ccccc1CO2 | ClC\C=C/1\C2=C(OCC3=C1C=CC=C3)C=CC(=C2)C(=O)OC.[N+](=O)([O-])C1=CC2=C(N=CN2)C=C1>>[N+](=O)([O-])C1=CC2=C(N(C=N2)C\C=C/2\C3=C(OCC4=C2C=CC=C4)C=CC(=C3)C(=O)OC)C=C1.[N+](=O)([O-])C=1C=CC2=C(N(C=N2)C\C=C/2\C3=C(OCC4=C2C=CC=C4)C=CC(=C3)C(=O)OC)C1 | Cl[CH2:46]/[CH:45]=[C:44]1/[c:42]2[c:41]([cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:43]2)[O:66][CH2:65][c:64]2[c:59]1[cH:60][cH:8][cH:62][cH:63]2.[n:14]1[c:25]2[c:17]([nH:16][cH:48]1)[cH:18][c:19]([N+:20]([O-:21])=[O:37])[cH:23][cH:24]2>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)/[C:11](=[CH:... | COC(=O)c1ccc2c(c1)/C(=C/CCl)c1ccccc1CO2.O=[N+]([O-])c1ccc2nc[nH]c2c1 | COC(=O)c1ccc2c(c1)/C(=C/Cn1cnc3cc([N+](=O)[O-])ccc31)c1ccccc1CO2.COC(=O)c1ccc2c(c1)/C(=C/Cn1cnc3ccc([N+](=O)[O-])cc31)c1ccccc1CO2 | null | null | null | Aromatic Heterocycle Formation | N-alkylation of secondary amines with alkyl halides | 7e1ebc300652767c1ba0f2cb08dcd922def11d82561506a602e80d4c7ebf0073 | 1cabd9b76881c312ea84a6144c7dd514901969b37511b9dd2a538c6687cc36ea | C(\Cn1cnc2ccccc21)=C1\c2ccccc2COc2ccccc21.C(\Cn1cnc2ccccc21)=C1\c2ccccc2COc2ccccc21 | Cl-[CH2;D2;+0:1]/[C:2]=[C:3]1/[c:4]2:[cH;D2;+0:5]:[c;H0;D3;+0:6](-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10]):[c:11]:[cH;D2;+0:12]:[c;H0;D3;+0:13]:2-[#8:14]-[C:15]-[c:16]2:[c:17]:[cH;D2;+0:18]:[cH;D2;+0:19]:[cH;D2;+0:20]:[c:21]:2-1.[O-;H0;D1:22]-[N+;H0;D3:23](=[O;H0;D1;+0:24])-[c:25]1:[c:26]:[c:27]2:[nH;D2;+0:28]:[cH;D2;+... | null | [] | null | null | null | null | Compound h, 2.0 g, and 5.2 g of 5-nitrobenzimidazole were treated in a manner similar to Example 23 to give a 1:1 mixture of Compounds E-55a and E-56a. The mixture was separated and purified by silica gel column chromatography (eluting solvent, hexane:ethyl acetate:triethylamine=10:10:1) to give 1.1 g of methyl (E)-11-... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ether.Nitro group | Ester.Ester.Ether.Ether.Nitro group.Nitro group | c1ccc2c(c1)COc1ccccc1C2.c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1.c1ccc2c(c1)COc1ccccc1C2.c1ccc2nc[nH]c2c1.c1ccc2c(c1)COc1ccccc1C2 | c1ccc2[nH]cnc2c1.c1ccc2c(c1)COc1ccccc1C2.c1ccc2nc[nH]c2c1.c1ccc2c(c1)COc1ccccc1C2 | null | null | null | null | COC(=O)c1ccc2c(c1)/C(=C/CCl)c1ccccc1CO2.O=[N+]([O-])c1ccc2nc[nH]c2c1>>COC(=O)c1ccc2c(c1)/C(=C/Cn1cnc3cc([N+](=O)[O-])ccc31)c1ccccc1CO2.COC(=O)c1ccc2c(c1)/C(=C/Cn1cnc3ccc([N+](=O)[O-])cc31)c1ccccc1CO2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-598fc3b6cb7148718b860b1c0cc3f13a | COC(=O)c1ccc2c(c1)/C(=C/CCl)c1ccccc1CO2.COc1ccc2nc[nH]c2c1>>COC(=O)c1ccc2c(c1)/C(=C/Cn1cnc3cc(OC)ccc31)c1ccccc1CO2.COC(=O)c1ccc2c(c1)/C(=C/Cn1cnc3ccc(OC)cc31)c1ccccc1CO2 | ClC\C=C/1\C2=C(OCC3=C1C=CC=C3)C=CC(=C2)C(=O)OC.COC1=CC2=C(N=CN2)C=C1>>COC1=CC2=C(N(C=N2)C\C=C/2\C3=C(OCC4=C2C=CC=C4)C=CC(=C3)C(=O)OC)C=C1.COC=1C=CC2=C(N(C=N2)C\C=C/2\C3=C(OCC4=C2C=CC=C4)C=CC(=C3)C(=O)OC)C1 | Cl[CH2:45]/[CH:44]=[C:43]1\[c:25]2[cH:26][cH:1][cH:28][cH:29][c:30]2[CH2:31][O:32][c:8]2[cH:7][cH:6][c:5]([C:3](=[O:2])[O:53][CH3:54])[cH:42][c:41]21.[n:14]1[c:24]2[c:17]([nH:16][cH:47]1)[cH:18][c:19]([O:20][CH3:21])[cH:22][cH:23]2>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)/[C:11](=[CH:12]/[CH2:1... | COC(=O)c1ccc2c(c1)/C(=C/CCl)c1ccccc1CO2.COc1ccc2nc[nH]c2c1 | COC(=O)c1ccc2c(c1)/C(=C/Cn1cnc3cc(OC)ccc31)c1ccccc1CO2.COC(=O)c1ccc2c(c1)/C(=C/Cn1cnc3ccc(OC)cc31)c1ccccc1CO2 | null | null | null | Aromatic Heterocycle Formation | N-alkylation of secondary amines with alkyl halides | d6e6e92084a833b5f06ef03562947784629d954b3a1aeb49e16619fa89bec31b | 1cc6bab63a865ef44ee03fca7dea56d12880b8439b6cec426d04b2f3591d9e1b | C(\Cn1cnc2ccccc21)=C1\c2ccccc2COc2ccccc21.C(\Cn1cnc2ccccc21)=C1\c2ccccc2COc2ccccc21 | Cl-[CH2;D2;+0:1]/[C:2]=[C;H0;D3;+0:3]1\[c;H0;D3;+0:4]2:[cH;D2;+0:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:[c:8]:[c:9]:2-[C:10]-[#8:11]-[c;H0;D3;+0:12]2:[c:13]:[c:14]:[c;H0;D3;+0:15](-[C;H0;D3;+0:16](=[O;H0;D1;+0:17])-[O;H0;D2;+0:18]-[C;D1;H3:19]):[cH;D2;+0:20]:[c;H0;D3;+0:21]:2-1.[c:22]:[c:23]1:[nH;D2;+0:24]:[cH;D2;+0:25]:[n;H0;D2... | null | [] | null | null | null | null | Compound h, 2.9 g, and 4.2 g of 5-methoxybenzimidazole were treated in a manner similar to Example 23 to give a 1:1 mixture of Compounds E-61a and E-62a. The mixture was separated and purified by silica gel column chromatography (eluting solvent, hexane:ethyl acetate:triethylamine=10:10:1) to give 0.8 g of methyl (E)-1... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ether | Ester.Ester.Ether.Ether.Ether | c1ccc2c(c1)COc1ccccc1C2.c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1.c1ccc2c(c1)COc1ccccc1C2.c1ccc2nc[nH]c2c1.c1ccc2c(c1)COc1ccccc1C2 | c1ccc2[nH]cnc2c1.c1ccc2c(c1)COc1ccccc1C2.c1ccc2nc[nH]c2c1.c1ccc2c(c1)COc1ccccc1C2 | null | null | null | null | COC(=O)c1ccc2c(c1)/C(=C/CCl)c1ccccc1CO2.COc1ccc2nc[nH]c2c1>>COC(=O)c1ccc2c(c1)/C(=C/Cn1cnc3cc(OC)ccc31)c1ccccc1CO2.COC(=O)c1ccc2c(c1)/C(=C/Cn1cnc3ccc(OC)cc31)c1ccccc1CO2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c5ae183eb4bd4d98998488c4391b784a | COC(=O)c1ccc2c(c1)/C(=C/CCl)c1ccccc1CO2.c1ccc2[nH]ccc2c1.c1ccc2[nH]cnc2c1>>COC(=O)c1ccc2c(c1)/C(=C/Cn1ccc3cccnc31)c1ccccc1CO2 | ClC\C=C/1\C2=C(OCC3=C1C=CC=C3)C=CC(=C2)C(=O)OC.N1=CNC2=C1C=CC=C2.N1C=CC2=CC=CC=C12>>N1(C=CC2=CC=CN=C12)C\C=C/1\C2=C(OCC3=C1C=CC=C3)C=CC(=C2)C(=O)OC | Cl[CH2:13]/[CH:12]=[C:11]1/[c:9]2[c:8]([cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:10]2)[O:30][CH2:29][c:28]2[c:23]1[cH:24][cH:25][cH:26][cH:27]2.c1ccc2c(c1)[nH:14][cH:15][cH:16]2.c1[nH][c:17]2[cH:18][cH:19][cH:20]c[c:22]2[n:21]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)/[C:11](=[CH:12]/[CH2... | COC(=O)c1ccc2c(c1)/C(=C/CCl)c1ccccc1CO2.c1ccc2[nH]ccc2c1.c1ccc2[nH]cnc2c1 | COC(=O)c1ccc2c(c1)/C(=C/Cn1ccc3cccnc31)c1ccccc1CO2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 7aaf707baa042bfcf8c993ba1304ef4d06ea6bf4ccd12e7be3cc81ba479c3dc4 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | C(\Cn1ccc2cccnc21)=C1\c2ccccc2COc2ccccc21 | Cl-[CH2;D2;+0:1]/[C:2]=[C:3](\[c:4](:[c:5]):[c:6])-[c:7](:[c:8]):[c:9]-[#8:10].[c:11]1:[cH;D2;+0:12]:c2:c:c:c:c:c:2:[nH;D2;+0:13]:1.[c:14]1:[c:15]:[cH;D2;+0:16]:c:[c;H0;D3;+0:17]2:[n;H0;D2;+0:18]:c:[nH]:[c;H0;D3;+0:19]:1:2>>[#8:10]-[c:9]:[c:7](:[c:8])/[C:3](=[C:2]/[CH2;D2;+0:1]-[n;H0;D3;+0:13]1:[c:11]:[cH;D2;+0:12]:[c;... | null | [] | null | null | null | null | In Examples 40 through 49, the products were prepared in a manner similar to Example 23, using Compound h and the corresponding benzimidazole or indole derivatives.
Conditions: See reaction.notes.procedure_details.
Workup: In Examples 40 through 49, the products were prepared in a manner similar to Example 23 | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1.c1ccc2[nH]cnc2c1 | c1cnc2[nH]ccc2c1 | c1cnc2[nH]ccc2c1.c1ccc2c(c1)COc1ccccc1C2 | HCl | null | null | null | COC(=O)c1ccc2c(c1)/C(=C/CCl)c1ccccc1CO2.c1ccc2[nH]ccc2c1.c1ccc2[nH]cnc2c1>>COC(=O)c1ccc2c(c1)/C(=C/Cn1ccc3cccnc31)c1ccccc1CO2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4b945c0b929b49f888af2cd922c9349b | COC(=O)c1ccc2c(c1)C(O)c1ccccc1CO2.O=S([O-])c1ccccc1>>COC(=O)c1ccc2c(c1)C(S(=O)(=O)c1ccccc1)c1ccccc1CO2 | OC1C2=C(OCC3=C1C=CC=C3)C=CC(=C2)C(=O)OC.O.O.C1(=CC=CC=C1)S(=O)[O-].[Na+].FC(C(=O)OC(C(F)(F)F)=O)(F)F>>C1(=CC=CC=C1)S(=O)(=O)C1C2=C(OCC3=C1C=CC=C3)C=CC(=C2)C(=O)OC | O[CH:11]1[c:9]2[c:8]([cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:10]2)[O:28][CH2:27][c:26]2[c:21]1[cH:22][cH:23][cH:24][cH:25]2.[S:12]([O-:13])(=[O:14])[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH:11]([S:12](=[O:13])(=[O:14])[c:15]1[cH:16][cH:17][c... | COC(=O)c1ccc2c(c1)C(O)c1ccccc1CO2.O=S([O-])c1ccccc1 | COC(=O)c1ccc2c(c1)C(S(=O)(=O)c1ccccc1)c1ccccc1CO2 | null | null | null | Oxidation | OtherReaction | 0cb4aff1d4360fb1790c2fa5595c8971eb1966ac28470b3ea02e7d101c7d8289 | 938a6acf48abd4751d9911dc70293bba718da507a85ffbf95be2f2bc8cc1324b | O=S(=O)(c1ccccc1)C1c2ccccc2COc2ccccc21 | O-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7]-[#8:8].[O-;H0;D1:9]-[S;H0;D3;+0:10](=[O;D1;H0:11])-[c:12](:[c:13]):[c:14]>>[#8:8]-[c:7]:[c:5](:[c:6])-[CH;D3;+0:1](-[S;H0;D4;+0:10](=[O;D1;H0:11])(=[O;H0;D1;+0:9])-[c:12](:[c:13]):[c:14])-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | Compound b, 10 g, 15 g of sodium benzenesulfinate dihydrate and 25 ml of trifluoroacetic anhydride were treated in a manner similar to Example 109 to give 14.3 g of the objective compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Sulfone | c1ccc2c(c1)COc1ccccc1C2 | c1ccc2c(c1)COc1ccccc1C2 | c1ccccc1.c1ccc2c(c1)COc1ccccc1C2 | HO- | null | null | null | COC(=O)c1ccc2c(c1)C(O)c1ccccc1CO2.O=S([O-])c1ccccc1>>COC(=O)c1ccc2c(c1)C(S(=O)(=O)c1ccccc1)c1ccccc1CO2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f1b3d2d807af4226b0d71e242805c55b | COC(=O)c1ccc2c(c1)C(NC(=O)CCl)c1ccccc1CO2.c1c[nH]cn1>>COC(=O)c1ccc2c(c1)C(NC(=O)Cn1ccnc1)c1ccccc1CO2 | ClCC(=O)NC1C2=C(OCC3=C1C=CC=C3)C=CC(=C2)C(=O)OC.N1C=NC=C1>>N1(C=NC=C1)CC(=O)NC1C2=C(OCC3=C1C=CC=C3)C=CC(=C2)C(=O)OC | Cl[CH2:15][C:13]([NH:12][CH:11]1[c:9]2[c:8]([cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:10]2)[O:28][CH2:27][c:26]2[c:21]1[cH:22][cH:23][cH:24][cH:25]2)=[O:14].[nH:16]1[cH:17][cH:18][n:19][cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH:11]([NH:12][C:13](=[O:14])[CH2:15][n:16]1[cH:17][cH... | COC(=O)c1ccc2c(c1)C(NC(=O)CCl)c1ccccc1CO2.c1c[nH]cn1 | COC(=O)c1ccc2c(c1)C(NC(=O)Cn1ccnc1)c1ccccc1CO2 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b9d84e1ee028da6e8c5d8924d45fbf8f3755d9adc2caf0035bd5ed7f30f5ee03 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=C(Cn1ccnc1)NC1c2ccccc2COc2ccccc21 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[C:5].[#7;a:6]1:[c:7]:[c:8]:[nH;D2;+0:9]:[c:10]:1>>[C:5]-[#7:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[c:8]:[c:7]:[#7;a:6]:[c:10]:1 | null | [] | null | null | null | null | Crude methyl 11-chloroacetamido-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate, 3.0 g, was heated to reflux for 4 hours in 100 ml of toluene together with 0.9 g of imidazole. After allowing to cool, the solvent was distilled off under reduced pressure. The obtained residue was extracted with 300 ml of methylene chloride. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccc2c(c1)COc1ccccc1C2 | HCl | C1(=CC=CC=C1)C | null | null | COC(=O)c1ccc2c(c1)C(NC(=O)CCl)c1ccccc1CO2.c1c[nH]cn1>C1(=CC=CC=C1)C>COC(=O)c1ccc2c(c1)C(NC(=O)Cn1ccnc1)c1ccccc1CO2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-45d98123cfe540de8a4f1e9fe87d5c88 | COC(=O)c1ccc2c(c1)/C(=C/CCl)c1ccccc1CO2.c1ccncc1>>COC(=O)c1ccc2c(c1)/C(=C/Cc1cccnc1)c1ccccc1CO2 | ClC\C=C/1\C2=C(OCC3=C1C=CC=C3)C=CC(=C2)C(=O)OC.N1=CC=CC=C1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>N1=CC(=CC=C1)C\C=C/1\C2=C(OCC3=C1C=CC=C3)C=CC(=C2)C(=O)OC | Cl[CH2:13]/[CH:12]=[C:11]1/[c:9]2[c:8]([cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:10]2)[O:27][CH2:26][c:25]2[c:20]1[cH:21][cH:22][cH:23][cH:24]2.[cH:14]1[cH:15][cH:16][cH:17][n:18][cH:19]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)/[C:11](=[CH:12]/[CH2:13][c:14]1[cH:15][cH:16][cH:17][n:18][c... | COC(=O)c1ccc2c(c1)/C(=C/CCl)c1ccccc1CO2.c1ccncc1 | COC(=O)c1ccc2c(c1)/C(=C/Cc1cccnc1)c1ccccc1CO2 | null | null | O1CCCC1 | C-C Coupling | Friedel-Crafts alkylation with halide | c918ab2b340de388cade9a755e451a5b4caeb6b1c32b83fb98e425e917520b3b | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | C(\Cc1cccnc1)=C1\c2ccccc2COc2ccccc21 | Cl-[CH2;D2;+0:1]/[C:2]=[C:3](\[c:4](:[c:5]):[c:6])-[c:7](:[c:8]):[c:9]-[#8:10].[#7;a:11]1:[c:12]:[c:13]:[c:14]:[cH;D2;+0:15]:[c:16]:1>>[#8:10]-[c:9]:[c:7](:[c:8])/[C:3](=[C:2]/[CH2;D2;+0:1]-[c;H0;D3;+0:15]1:[c:14]:[c:13]:[c:12]:[#7;a:11]:[c:16]:1)-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | To 50 ml of pyridine was added to 2.0 g of lithium aluminum hydride, and the mixture was stirred at room temperature for one night. Then, 90 ml of tetrahydrofuran solution containing 5.0 g of Compound h was dropwise added thereto under ice-cooling. The mixture was stirred at room temperature for 5 hours, and the solven... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccc2c(c1)COc1ccccc1C2 | HCl | O1CCCC1 | null | null | COC(=O)c1ccc2c(c1)/C(=C/CCl)c1ccccc1CO2.c1ccncc1>O1CCCC1>COC(=O)c1ccc2c(c1)/C(=C/Cc1cccnc1)c1ccccc1CO2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-092a67ae3ade42ac8570afefa1b804a7 | C=C1C2=C(C=CC1C(=O)OC)OCc1ccccc1C2.C=O.CN1CCNCC1>>COC(=O)c1ccc2c(c1)C(=CCN1CCN(C)CC1)c1ccccc1CO2 | CN1CCNCC1.C=O.C=C1C(C=CC=2OCC3=C(CC21)C=CC=C3)C(=O)OC.FC(C(=O)O)(F)F>>CN1CCN(CC1)CC=C1C2=C(OCC3=C1C=CC=C3)C=CC(=C2)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH:6]=[CH:7][C:8]2=[C:9]([C:10]1=[CH2:12])[CH2:11][c:21]1[cH:22][cH:23][cH:24][cH:25][c:26]1[CH2:27][O:28]2.O=[CH2:13].[NH:14]1[CH2:15][CH2:16][N:17]([CH3:18])[CH2:19][CH2:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[C:11](=[CH:12][CH2:13][N:14]1[CH2:15][CH2:16... | C=C1C2=C(C=CC1C(=O)OC)OCc1ccccc1C2.C=O.CN1CCNCC1 | COC(=O)c1ccc2c(c1)C(=CCN1CCN(C)CC1)c1ccccc1CO2 | null | null | ClCC(Cl)(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 090402fd07aed4fbada2a9ce250a1c6681fbac2918890b15d593f3ec90c578b0 | 0b00c9d6bb53bace52beab9774fd6b6eda9f2144bc5fa41edef9b1edd487818c | C(CN1CCNCC1)=C1c2ccccc2COc2ccccc21 | O=[CH2;D1;+0:1].[#7:2]1-[C:3]-[C:4]-[NH;D2;+0:5]-[C:6]-[C:7]-1.[C;D1;H3:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[CH;D3;+0:12]1-[CH;D2;+0:13]=[CH;D2;+0:14]-[C;H0;D3;+0:15]2=[C;H0;D3;+0:16](-[CH2;D2;+0:17]-[c:18](:[c:19]):[c:20]-[C:21]-[#8:22]-2)-[C;H0;D3;+0:23]-1=[CH2;D1;+0:24]>>[C;D1;H3:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[c;H0;D3... | null | [] | 60 | CELSIUS | 2 | HOUR | 1-Methylpiperazine, 30 ml, and 74 g of paraformaldehyde were dissolved in 2 l of tetrachloroethane and 100 ml of trifluoroacetic acid was dropwise added to the solution. After stirring at 60° C. for 2 hours, a solution of 36 g of methyl 1-methylene-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate in 600 ml of tetrachloroeth... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Ester.Ether.Secondary amine.Vinyl | Ester.Ether.Tertiary amine | C1=CC2=C(CC1)Cc1ccccc1CO2.C1CNCC[NH]1 | C1C[NH]CC[NH]1.c1ccc2c(c1)COc1ccccc1C2 | C1C[NH]CC[NH]1.c1ccc2c(c1)COc1ccccc1C2 | HO- | ClCC(Cl)(Cl)Cl | 60 | 2 | C=C1C2=C(C=CC1C(=O)OC)OCc1ccccc1C2.C=O.CN1CCNCC1>ClCC(Cl)(Cl)Cl>COC(=O)c1ccc2c(c1)C(=CCN1CCN(C)CC1)c1ccccc1CO2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8aee444aa73b42c2854984330a5ca68e | COC(=O)c1ccc2c(c1)C(O)c1ccccc1CO2.OCCS>>COC(=O)c1ccc2c(c1)C(SCCO)c1ccccc1CO2 | OC1C2=C(OCC3=C1C=CC=C3)C=CC(=C2)C(=O)OC.FC(C(=O)OC(C(F)(F)F)=O)(F)F.SCCO>>OCCSC1C2=C(OCC3=C1C=CC=C3)C=CC(=C2)C(=O)OC | O[CH:11]1[c:9]2[c:8]([cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:10]2)[O:23][CH2:22][c:21]2[c:16]1[cH:17][cH:18][cH:19][cH:20]2.[SH:12][CH2:13][CH2:14][OH:15]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH:11]([S:12][CH2:13][CH2:14][OH:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[CH2:22][O:2... | COC(=O)c1ccc2c(c1)C(O)c1ccccc1CO2.OCCS | COC(=O)c1ccc2c(c1)C(SCCO)c1ccccc1CO2 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | fd4fd3db62ae9168fca465f97f0ea27930b857801948c9eb42791078b5f5432e | 1adaf4bbc2a7f61dc5a5c5683fc35a8688451e76ea039960fc2b46664e762df6 | c1ccc2c(c1)COc1ccccc1C2 | O-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7]-[#8:8].[C:9]-[C:10]-[SH;D1;+0:11]>>[#8:8]-[c:7]:[c:5](:[c:6])-[CH;D3;+0:1](-[S;H0;D2;+0:11]-[C:10]-[C:9])-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | In 400 ml of methylene chloride was suspended 40.0 g of Compound b obtained in Reference Example 2. Trifluoroacetic anhydride, 21.0 ml, was added to the suspension followed by stirring at room temperature for an hour. Them, 10.7 ml of 2-mercaptoethanol was added to the mixture followed by stirring for further 4 hours. ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Aliphatic thiol | Monosulfide | c1ccc2c(c1)COc1ccccc1C2 | c1ccc2c(c1)COc1ccccc1C2 | c1ccc2c(c1)COc1ccccc1C2 | HO- | C(Cl)Cl | null | null | COC(=O)c1ccc2c(c1)C(O)c1ccccc1CO2.OCCS>C(Cl)Cl>COC(=O)c1ccc2c(c1)C(SCCO)c1ccccc1CO2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ba4b6bc657a14ef6912c99577adeb904 | CCCCCC.COC1c2ccccc2COc2cc(Br)ccc21.O=C=O>>COC(=O)c1ccc2c(c1)OCc1ccccc1C2OC | S(O)(O)(=O)=O.C(CCC)[Li].CCCCCC.BrC=1C=CC2=C(OCC3=C(C2OC)C=CC=C3)C1.C(=O)=O>>COC1C2=C(OCC3=C1C=CC=C3)C=C(C=C2)C(=O)OC | CCCCC[CH3:1].Br[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[CH:19]2[O:20][CH3:21].[O:2]=[C:3]=[O:4]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[CH:19]2[O:20][CH3:21] | CCCCCC.COC1c2ccccc2COc2cc(Br)ccc21.O=C=O | COC(=O)c1ccc2c(c1)OCc1ccccc1C2OC | null | null | CO.O1CCCC1 | Acylation | OtherReaction | fa3449bb9598289c8530c4627b5ba4145d50e2e15607416639e0c5209dce6f68 | 9f70ae976742ba327fb41a3a0f3ab2f8b9d27b4c1b5cd75d70168c5c27eb44ef | c1ccc2c(c1)COc1ccccc1C2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[#8:4]):[c:5]:[c:6].C-C-C-C-C-[CH3;D1;+0:7].[O;D1;H0:8]=[C;H0;D2;+0:9]=[O;H0;D1;+0:10]>>[#8:4]-[c:3]:[c:2]:[c;H0;D3;+0:1](-[C;H0;D3;+0:9](=[O;D1;H0:8])-[O;H0;D2;+0:10]-[CH3;D1;+0:7]):[c:5]:[c:6] | null | [] | -78 | CELSIUS | 40 | MINUTE | 3-Bromo-11-methoxy-6,11-dihydrodibenz[b,e]oxepine, 30 g, was dissolved in 500 ml of tetrahydrofuran. After cooling to -78° C., 65 ml of 1.6 N n-butyl lithium/hexane solution was dropwise added to the solution in a nitrogen atmosphere followed by stirring at -78° C. for further 40 minutes. The reaction solution was drop... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbon dioxide | Ester | c1ccc2c(c1)COc1ccccc1C2 | c1ccc2c(c1)COc1ccccc1C2 | c1ccc2c(c1)COc1ccccc1C2 | HBr | CO.O1CCCC1 | -78 | 0.666667 | CCCCCC.COC1c2ccccc2COc2cc(Br)ccc21.O=C=O>CO.O1CCCC1>COC(=O)c1ccc2c(c1)OCc1ccccc1C2OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d9b4a74b6f174994bb36ba06d02ba840 | C[Si](C)(C)Cl.Cc1ccc(C)c(Br)c1>>Cc1ccc(C)c([Si](C)(C)C)c1 | Cl[Si](C)(C)C.BrC1=C(C=CC(=C1)C)C.CCCCCC.C(CCC)[Li]>>C[Si](C1=C(C=CC(=C1)C)C)(C)C | Cl[Si:8]([CH3:9])([CH3:10])[CH3:11].Br[c:7]1[c:5]([CH3:6])[cH:4][cH:3][c:2]([CH3:1])[cH:12]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH3:6])[c:7]([Si:8]([CH3:9])([CH3:10])[CH3:11])[cH:12]1 | C[Si](C)(C)Cl.Cc1ccc(C)c(Br)c1 | Cc1ccc(C)c([Si](C)(C)C)c1 | null | null | C(C)OCC | Functional Group Interconversion | OtherReaction | 78a3f96947a81aefa2c3ce31b78402b374f99e6c37137a3aa24732f86087b2f1 | 549d0cfaa9958a071151c96b5ba63e0c24c97775b4c805f43824d109bdd81241 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6].Cl-[Si;H0;D4;+0:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10]>>[C;D1;H3:8]-[Si;H0;D4;+0:7](-[C;D1;H3:9])(-[C;D1;H3:10])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6] | null | [] | null | null | 5 | HOUR | To a stirred solution of 1.0M of 2-bromo-p-xylene in diethyl ether at 0° C. was added n-butyllithium hexane solution solwly, and the mixture was stirrd for 5 hr. To the above reaction mixture was added 1.0M of chlorotrimethylsilane as dropwise and it was stirred for 24 hr. The solvent was removed under reduced pressure... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Silyl protective group | Silyl protective group | c1ccccc1 | c1ccccc1 | c1ccccc1 | Br- | C(C)OCC | null | 5 | C[Si](C)(C)Cl.Cc1ccc(C)c(Br)c1>C(C)OCC>Cc1ccc(C)c([Si](C)(C)C)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a6e9045e32c049c09013afb37b5d1d71 | C[Si](C)(C)Cl.Cc1cc(C)cc(Br)c1>>Cc1cc(C)cc([Si](C)(C)C)c1 | BrC=1C=C(C=C(C1)C)C.Cl[Si](C)(C)C>>C[Si](C=1C=C(C=C(C1)C)C)(C)C | Cl[Si:8]([CH3:9])([CH3:10])[CH3:11].Br[c:7]1[cH:6][c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:12]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:7]([Si:8]([CH3:9])([CH3:10])[CH3:11])[cH:12]1 | C[Si](C)(C)Cl.Cc1cc(C)cc(Br)c1 | Cc1cc(C)cc([Si](C)(C)C)c1 | null | null | null | Functional Group Interconversion | OtherReaction | 78a3f96947a81aefa2c3ce31b78402b374f99e6c37137a3aa24732f86087b2f1 | 549d0cfaa9958a071151c96b5ba63e0c24c97775b4c805f43824d109bdd81241 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].Cl-[Si;H0;D4;+0:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[C;D1;H3:9]>>[C;D1;H3:7]-[Si;H0;D4;+0:6](-[C;D1;H3:8])(-[C;D1;H3:9])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | In the same manner as described in preparation 1, 5-bromo-m-xylene was allowed to react with chlorotrimethylsilane, and afforded TSIX. The yield and properties of product are summarized in Table 1.
Conditions: See reaction.notes.procedure_details.
Workup: afforded TSIX; The yield | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Silyl protective group | Silyl protective group | c1ccccc1 | c1ccccc1 | c1ccccc1 | Br- | null | null | null | C[Si](C)(C)Cl.Cc1cc(C)cc(Br)c1>>Cc1cc(C)cc([Si](C)(C)C)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-55b62a5f55db48bfae40873d928c5459 | Cc1cc(C)cc(Br)c1.Cl[Si](c1ccccc1)(c1ccccc1)c1ccccc1>>Cc1cc(C)cc([Si](c2ccccc2)(c2ccccc2)c2ccccc2)c1 | BrC=1C=C(C=C(C1)C)C.Cl[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>C1(=CC=CC=C1)[Si](C=1C=C(C=C(C1)C)C)(C1=CC=CC=C1)C1=CC=CC=C1 | Br[c:7]1[cH:6][c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:27]1.Cl[Si:8]([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:7]([Si:8]([c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)([c:15]2[cH:16][cH:17][cH:... | Cc1cc(C)cc(Br)c1.Cl[Si](c1ccccc1)(c1ccccc1)c1ccccc1 | Cc1cc(C)cc([Si](c2ccccc2)(c2ccccc2)c2ccccc2)c1 | null | null | null | Functional Group Interconversion | OtherReaction | 78a3f96947a81aefa2c3ce31b78402b374f99e6c37137a3aa24732f86087b2f1 | 549d0cfaa9958a071151c96b5ba63e0c24c97775b4c805f43824d109bdd81241 | c1ccc([Si](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].Cl-[Si;H0;D4;+0:6](-[c:7](:[c:8]):[c:9])(-[c:10](:[c:11]):[c:12])-[c:13](:[c:14]):[c:15]>>[c:14]:[c:13](-[Si;H0;D4;+0:6](-[c:7](:[c:8]):[c:9])(-[c:10](:[c:11]):[c:12])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:15] | null | [] | null | null | null | null | In the same manner as described in preparation 1, 5-bromo-m-xylene was allowed to react with chlorotriphenylsilane, and afforded TPSIX. The yield and properties are summarized in Table 1.
Conditions: See reaction.notes.procedure_details.
Workup: afforded TPSIX; The yield | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Silyl protective group | Silyl protective group | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Br- | null | null | null | Cc1cc(C)cc(Br)c1.Cl[Si](c1ccccc1)(c1ccccc1)c1ccccc1>>Cc1cc(C)cc([Si](c2ccccc2)(c2ccccc2)c2ccccc2)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-90395268b2774bc9b14694b06a459c4d | O=[N+]([O-])c1cccc(O)c1.OCCOCCOCCCl>>O=[N+]([O-])c1cccc(OCCOCCOCCO)c1 | ClCCOCCOCCO.[N+](=O)([O-])C=1C=C(C=CC1)O.CN(C=O)C.C([O-])([O-])=O.[K+].[K+]>>[N+](=O)([O-])C=1C=C(OCCOCCOCCO)C=CC1 | [O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:19]1.Cl[CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][OH:18]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][OH:18])[cH:19]1 | O=[N+]([O-])c1cccc(O)c1.OCCOCCOCCCl | O=[N+]([O-])c1cccc(OCCOCCOCCO)c1 | null | null | O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | While stirring a mixture of 27.8 g of m-nitrophenol, 120 ml of N,N-dimethylformamide, and 25 g of potassium carbonate at 80° C., 37 g of 2-(2-(2-chloroethoxy)ethoxy)-ethanol was added dropwise to the mixture. After stirring the mixture for one hour at 80° C., 200 ml of ethyl acetate and 200 ml of water were added to th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HCl | O.C(C)(=O)OCC | null | null | O=[N+]([O-])c1cccc(O)c1.OCCOCCOCCCl>O.C(C)(=O)OCC>O=[N+]([O-])c1cccc(OCCOCCOCCO)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3c1df7ab18894dd9a67c2c7d77a2304e | C=C(C)C(=O)OCCOCCOCCOc1cccc([N+](=O)[O-])c1>>C=C(C)C(=O)OCCOCCOCCOc1cccc(N)c1 | C(C(=C)C)(=O)OCCOCCOCCOC1=CC(=CC=C1)[N+](=O)[O-].[Cl-].[NH4+].O.C(C)(C)O>>C(C(=C)C)(=O)OCCOCCOCCOC1=CC(=CC=C1)N | O=[N+:21]([O-])[c:20]1[cH:19][cH:18][cH:17][c:16]([O:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][C:4]([C:2](=[CH2:1])[CH3:3])=[O:5])[cH:22]1>>[CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][c:16]1[cH:17][cH:18][cH:19][c:20]([NH2:21])[cH:22]1 | C=C(C)C(=O)OCCOCCOCCOc1cccc([N+](=O)[O-])c1 | C=C(C)C(=O)OCCOCCOCCOc1cccc(N)c1 | null | null | C(C)(=O)OCC | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 75 | CELSIUS | null | null | A mixture of 25 g of reduced iron, 1 g of ammonium chloride, 50 ml of water, and 250 ml of isopropyl alcohol was raised to a temperature of 75° C. with stirring and after adding dropwise an ethyl acetate solution of the compound (1-B) to the aqueous solution (the mixture) over a period of one hour, the resultant mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | C(C)(=O)OCC | 75 | null | C=C(C)C(=O)OCCOCCOCCOc1cccc([N+](=O)[O-])c1>C(C)(=O)OCC>C=C(C)C(=O)OCCOCCOCCOc1cccc(N)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-65ea4057d75b4366aba54ef2265871f0 | C=C(C)C(=O)Cl.OCCOCc1csc(Br)c1>>C=C(C)C(=O)OCC(OC)c1csc(Br)c1 | C(C(=C)C)(=O)Cl.BrC=1SC=C(C1)COCCO.N1=CC=CC=C1.C(C)#N.O>>C(C(=C)C)(=O)OCC(OC)C=1C=C(SC1)Br | Cl[C:4]([C:2](=[CH2:1])[CH3:3])=[O:5].[OH:6][CH2:7][CH2:10][O:9][CH2:8][c:11]1[cH:12][s:13][c:14]([Br:15])[cH:16]1>>[CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][CH2:7][CH:8]([O:9][CH3:10])[c:11]1[cH:12][s:13][c:14]([Br:15])[cH:16]1 | C=C(C)C(=O)Cl.OCCOCc1csc(Br)c1 | C=C(C)C(=O)OCC(OC)c1csc(Br)c1 | null | null | C(C)(=O)OCC | Acylation | OtherReaction | 8827e0fcc461d0f0605862cfbfc1a6a7bc1f9401bb989fec3176036ac26b1c0c | fe6f7c7f61effd090c2896f86afe02b12d2f7ec42ff986152c6d99c555fc94d4 | c1ccsc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[C;D1;H2:4])-[C;D1;H3:5].[OH;D1;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[#8:9]-[CH2;D2;+0:10]-[c:11]1:[c:12]:[#16;a:13]:[c:14]:[c:15]:1>>[C;D1;H2:4]=[C:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:6]-[CH2;D2;+0:7]-[CH;D3;+0:10](-[#8:9]-[CH3;D1;+0:8])-[c:11]1:[c:12]:[#16;a:1... | null | [] | null | null | null | null | While stirring a mixture of 0.1 mol of 2-bromo-4-2-hydroxyethoxymethylthiophene, 0.1 mol of pyridine, and 100 ml of acetonitrile at a temperature of lower than 10° C., 0.1 mol of methacryloyl chloride was added dropwise to the mixture over a period of 30 minutes. After stirring the mixture for one hour, 200 ml of ethyl... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary alcohol | Ester.Ether | null | null | c1ccsc1 | HCl | C(C)(=O)OCC | null | null | C=C(C)C(=O)Cl.OCCOCc1csc(Br)c1>C(C)(=O)OCC>C=C(C)C(=O)OCC(OC)c1csc(Br)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5f1016e69d7f473b92e9112c6cc82462 | CCNCC.O=C(Cc1ccccc1)Cc1ccccc1.O=CC=Cc1ccccc1>>O=C1C(c2ccccc2)=C(c2ccccc2)CCC1c1ccccc1.Oc1c(-c2ccccc2)ccc(-c2ccccc2)c1-c1ccccc1 | C(C1=CC=CC=C1)C(=O)CC1=CC=CC=C1.C(C=CC1=CC=CC=C1)=O.C(C)NCC>>C1(=CC=CC=C1)C1=C(C(=CC=C1C1=CC=CC=C1)C1=CC=CC=C1)O.C1(=CC=CC=C1)C=1C(C(CCC1C1=CC=CC=C1)C1=CC=CC=C1)=O | N([CH2:10][CH3:33])[CH2:31][CH3:32].[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1.[O:26]=[CH:35][CH:36]=[CH:37][c:38]1[cH:39][cH:40][cH:41][cH:42][cH:43]1>>[O:1]=[C:2]1[C:3]([c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)=[C:10]([c:11]2[cH:12][cH:13][cH:14][cH:15][c... | CCNCC.O=C(Cc1ccccc1)Cc1ccccc1.O=CC=Cc1ccccc1 | O=C1C(c2ccccc2)=C(c2ccccc2)CCC1c1ccccc1.Oc1c(-c2ccccc2)ccc(-c2ccccc2)c1-c1ccccc1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | f919ea78331796f8ba3d2901cb74d9c169ed576be44e8621457e0014426d70f4 | ef1ce48219dc67536ed625f61651543a70ca665d5df6e66a1d9d9b7c5087bbaa | O=C1C(c2ccccc2)=C(c2ccccc2)CCC1c1ccccc1.c1ccc(-c2ccc(-c3ccccc3)c(-c3ccccc3)c2)cc1 | [CH3;D1;+0:1]-[CH2;D2;+0:2]-N-[CH2;D2;+0:3]-[CH3;D1;+0:4].[O;D1;H0:5]=[C:6](-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10])-[CH2;D2;+0:11]-[c:12](:[c:13]):[c:14].[O;H0;D1;+0:15]=[CH;D2;+0:16]-[CH;D2;+0:17]=[CH;D2;+0:18]-[c;H0;D3;+0:19](:[c:20]:[c:21]):[c:22]:[c:23]>>[O;D1;H0:5]=[C:6]1-[C;H0;D3;+0:11](-[c:12](:[c:13]):[c:14])=[C;H... | 91 | [{"value": 91.0, "product": "C1(=CC=CC=C1)C=1C(C(CCC1C1=CC=CC=C1)C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 2,3,6-Triphenylphenol was prepared according to A. S. Hay and R. F. Clark (Macromolecules, 3, 533, 1970). 11.36 g (54 mmoles) of dibenzylketone, 7.14 g (54 mmoles) of cinnamaldehyde and 5 mL of diethylamine were mixed and the solution became yellow and after 20 min. a yellow solid deposited. The solid was added to etha... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone.Secondary amine | Ketone.Aromatic alcohol | null | C1=CCCCC1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | C1=CCCCC1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | C(C)O | null | 0.333333 | CCNCC.O=C(Cc1ccccc1)Cc1ccccc1.O=CC=Cc1ccccc1>C(C)O>O=C1C(c2ccccc2)=C(c2ccccc2)CCC1c1ccccc1.Oc1c(-c2ccccc2)ccc(-c2ccccc2)c1-c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-53a7d6a899654a0bba76c803935dd95c | COC(=O)c1ccc(CBr)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>COC(=O)c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1.[Br-] | COC(=O)C1=CC=C(C=C1)CBr.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>[Br-].C(=O)(OC)C1=CC=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][Br:31])[cH:29][cH:30]1.[P:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][P+:10]([c:11]2[cH:12][cH:13][cH:14][cH:15]... | COC(=O)c1ccc(CBr)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | COC(=O)c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1.[Br-] | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 72a5231b07f184f0ef4a0648badd4176f521b95f1ba3340a0f90d8894af47260 | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5].[c:6]:[c:7](-[P;H0;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:15]>>[Br-;H0;D0:1].[c:6]:[c:7](-[P+;H0;D4:8](-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5])(-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:15] | 90.9 | [{"value": 89.0, "product": "[Br-].C(=O)(OC)C1=CC=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.9, "product": "[Br-].C(=O)(OC)C1=CC=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a 2 L 3-neck round bottom flask fitted with a glass stopper, rubber septum, and reflux condenser with a nitrogen inlet tube, was added 64.90 g (283 mmol) methyl 4-bromomethyl benzoate, 81.74 g (311 mmol) triphenylphosphine, and 744 mL toluene. The solution was heated at 80° C. for 5 h. After cooling to room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | C1(=CC=CC=C1)C | 80 | null | COC(=O)c1ccc(CBr)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>C1(=CC=CC=C1)C>COC(=O)c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1.[Br-] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-bdab6112829f4164810a4a13bdd2db90 | COC(=O)c1ccc(C=O)cc1.COC(=O)c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>>COC(=O)c1ccc(C=Cc2ccc(C(=O)OC)cc2)cc1 | [Br-].C(=O)(OC)C1=CC=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C(=O)C1=CC=C(C(=O)OC)C=C1.C[O-].[Na+].C1(=CC=CC=C1)C>>C(=O)(OC)C1=CC=C(C=C1)C=CC1=CC=C(C=C1)C(=O)OC | O=[CH:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:22][cH:21]1.c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:10][c:11]2[cH:12][cH:13][c:14]([C:15](=[O:16])[O:17][CH3:18])[cH:19][cH:20]2)cc1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH:9]=[CH:10][c:11]2[cH:12][cH:13][c:14]([C:15](=[O:16])[O:17][CH3:18])[cH:19][... | COC(=O)c1ccc(C=O)cc1.COC(=O)c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | COC(=O)c1ccc(C=Cc2ccc(C(=O)OC)cc2)cc1 | null | null | CO | C-C Coupling | Wittig with Phosphonium | cb5f277ac55a0e763ef643becc05f1522019cc4161daceb249ed2d634b78153b | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | C(=Cc1ccccc1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[c:5]:[c:6](-[CH2;D2;+0:7]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[c:8]>>[c:5]:[c:6](-[CH;D2;+0:7]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | 79.3 | [{"value": 79.0, "product": "C(=O)(OC)C1=CC=C(C=C1)C=CC1=CC=C(C=C1)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.3, "product": "C(=O)(OC)C1=CC=C(C=C1)C=CC1=CC=C(C=C1)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a 2 L 3-neck round bottom flask fitted with a glass stopper, rubber septum, and reflux condenser with a nitrogen inlet tube, was added 126.35 g (251 mmol) (4-carbomethoxy)benzyltriphenylphosphonium bromide, 49.45 g (302 mmol) methyl 4-formylbenzoate, and 632 mL 2:1 methanol:toluene. After the starting material disso... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1.c1ccccc1 | HO- | CO | null | null | COC(=O)c1ccc(C=O)cc1.COC(=O)c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>CO>COC(=O)c1ccc(C=Cc2ccc(C(=O)OC)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-18f6ecb57450401ca2ce0553ff54682c | CO.O=C(O)C=Cc1ccc(O)cc1>>COC(=O)C=Cc1ccc(O)cc1 | OC1=CC=C(C=CC(=O)O)C=C1.CO.S(O)(O)(=O)=O>>OC1=CC=C(C=CC(=O)OC)C=C1 | [CH3:1][OH:2].O[C:3](=[O:4])[CH:5]=[CH:6][c:7]1[cH:8][cH:9][c:10]([OH:11])[cH:12][cH:13]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH:6][c:7]1[cH:8][cH:9][c:10]([OH:11])[cH:12][cH:13]1 | CO.O=C(O)C=Cc1ccc(O)cc1 | COC(=O)C=Cc1ccc(O)cc1 | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4]-[c:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C;D1;H3:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4]-[c:5] | 77.4 | [{"value": 77.0, "product": "OC1=CC=C(C=CC(=O)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.4, "product": "OC1=CC=C(C=CC(=O)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a 250 mL round bottom flask fitted with a reflux condenser and a nitrogen inlet tube was added 20.0 g (121.8 mmol) 4-hydroxycinnamic acid, 100 mL (246.9 mmol) methanol, and 5.0 g (50.0 mmol) concentrated sulfuric acid. The reaction vessel was heated at 75°-80° C. overnight. After cooling to room temperature, the res... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CO.O=C(O)C=Cc1ccc(O)cc1>>COC(=O)C=Cc1ccc(O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b688d55fe7ac489fafd16a933648d9bb | C[Si](C)(C)Cl.OCCCCO>>C[Si](C)(C)OCCCCO[Si](C)(C)C | C(CCCO)O.C[Si](C)(C)Cl>>[Si](C)(C)(C)OCCCCO[Si](C)(C)C | Cl[Si:2]([CH3:1])([CH3:4])[CH3:14].[OH:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10]>>[CH3:1][Si:2]([CH3:3])([CH3:4])[O:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][Si:11]([CH3:12])([CH3:13])[CH3:14] | C[Si](C)(C)Cl.OCCCCO | C[Si](C)(C)OCCCCO[Si](C)(C)C | null | null | C[Si](C)(C)N[Si](C)(C)C | Protection | OtherReaction | 365193c46066ba40e37d545479e23c55ebbe157298f3838b7598c16e342bb4eb | ba5efe7ef799923eafc7a66f1827ad0bbf5e2232ee7977532ee75affc88afb5e | null | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[CH3;D1;+0:4].[OH;D1;+0:5]-[C:6]-[C:7]-[C:8]-[C:9]-[OH;D1;+0:10]>>[C;D1;H3:11]-[#14:12](-[C;D1;H3:13])(-[CH3;D1;+0:4])-[O;H0;D2;+0:5]-[C:6]-[C:7]-[C:8]-[C:9]-[O;H0;D2;+0:10]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:14])-[C;D1;H3:3] | null | [] | 50 | CELSIUS | null | null | 1,4-Butanediol (54 g, 0.60 mol) was placed in a 500 mL 3-necked RB flask and treated with 0.3 mL trimethylsilyl chloride. A portion of HMDS (ca. 20 mL) was added, and an exothermic reaction took place as the mixture became homogeneous. The remainder of the HMDS (120 mL, 0.66 mol total) was added at a controlled rate (c... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary alcohol.Silyl protective group | Silyl protective group.Silyl protective group | null | null | null | null | C[Si](C)(C)N[Si](C)(C)C | 50 | null | C[Si](C)(C)Cl.OCCCCO>C[Si](C)(C)N[Si](C)(C)C>C[Si](C)(C)OCCCCO[Si](C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8970a9cd79a34b338559a5f59227a0d1 | C[Si](C)(C)Cl.OCCCCCO>>C[Si](C)(C)OCCCCCO[Si](C)(C)C | C(CCCCO)O.C[Si](C)(C)Cl>>[Si](C)(C)(C)OCCCCCO[Si](C)(C)C | Cl[Si:2]([CH3:1])([CH3:4])[CH3:15].[OH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11]>>[CH3:1][Si:2]([CH3:3])([CH3:4])[O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][Si:12]([CH3:13])([CH3:14])[CH3:15] | C[Si](C)(C)Cl.OCCCCCO | C[Si](C)(C)OCCCCCO[Si](C)(C)C | null | null | C[Si](C)(C)N[Si](C)(C)C | Protection | OtherReaction | 365193c46066ba40e37d545479e23c55ebbe157298f3838b7598c16e342bb4eb | ba5efe7ef799923eafc7a66f1827ad0bbf5e2232ee7977532ee75affc88afb5e | null | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[CH3;D1;+0:4].[C:5]-[C:6]-[OH;D1;+0:7].[C:8]-[C:9]-[OH;D1;+0:10]>>[C:8]-[C:9]-[O;H0;D2;+0:10]-[#14:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[CH3;D1;+0:4].[C:5]-[C:6]-[O;H0;D2;+0:7]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:14])-[C;D1;H3:3] | null | [] | 50 | CELSIUS | null | null | 1,5-Pentanediol (65 g, 0.62 mol) was placed in a 500 mL 3-necked RB flask and treated with 0.4 mL trimethylsilyl chloride. A portion of HMDS (ca. 20 mL) was added, and an exothermic reaction took place as the mixture became homogeneous. The remainder of the HMDS (130 mL, 0.71 mol total) was added at a controlled rate (... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary alcohol.Silyl protective group | Silyl protective group.Silyl protective group | null | null | null | null | C[Si](C)(C)N[Si](C)(C)C | 50 | null | C[Si](C)(C)Cl.OCCCCCO>C[Si](C)(C)N[Si](C)(C)C>C[Si](C)(C)OCCCCCO[Si](C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d1fe7d3fa2ed4eb4bae78796dd4fc1c8 | CC(O)CO.C[Si](C)(C)Cl>>CC(CO[Si](C)(C)C)O[Si](C)(C)C | C(C(C)O)O.C[Si](C)(C)Cl>>[Si](C)(C)(C)OC(C)CO[Si](C)(C)C | [CH3:1][CH:2]([CH2:3][OH:4])[OH:9].Cl[Si:5]([CH3:6])([CH3:7])[CH3:8]>>[CH3:1][CH:2]([CH2:3][O:4][Si:5]([CH3:6])([CH3:7])[CH3:8])[O:9][Si:10]([CH3:11])([CH3:12])[CH3:13] | CC(O)CO.C[Si](C)(C)Cl | CC(CO[Si](C)(C)C)O[Si](C)(C)C | null | null | C[Si](C)(C)N[Si](C)(C)C | Protection | OtherReaction | 7138891767541d5c289d40ba0b840e316bcd11bb85f8cf34540d1008add935f9 | 07dae459be8f7579bd9861f0533a71c817b2bdbb82e7c4c426c080de2eb90d8f | null | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;D1;H3:4].[C;D1;H3:5]-[C:6](-[OH;D1;+0:7])-[C:8]-[OH;D1;+0:9]>>[C;D1;H3:10]-[#14:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[O;H0;D2;+0:7]-[C:6](-[C;D1;H3:5])-[C:8]-[O;H0;D2;+0:9]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;D1;H3:4] | null | [] | null | null | null | null | 1,2-Propanediol (58.8 g, 0.77 mol) was placed in a 500 mL 3-necked RB flask and treated with 0.2 mL trimethylsilyl chloride. A small volume of HMDS (ca. 10 mL) was added, and an exothermic reaction took place as the mixture became homogeneous. The remainder of the HMDS (170 mL) was added at a controlled rate (ca. 3-5 m... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary alcohol.Silyl protective group | Silyl protective group.Silyl protective group | null | null | null | null | C[Si](C)(C)N[Si](C)(C)C | null | null | CC(O)CO.C[Si](C)(C)Cl>C[Si](C)(C)N[Si](C)(C)C>CC(CO[Si](C)(C)C)O[Si](C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5fbe3b2c7f8b498b94759a8c3fa8ca28 | C[C@@H](O)[C@H]1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)C(=O)[C@H](C)[C@H]12.C[N+]1(C)C[C@@H](S)C[C@H]1C(N)=O>>C[C@@H](O)[C@H]1C(=O)N2C(C(=O)[O-])=C(S[C@H]3C[C@@H](C(N)=O)[N+](C)(C)C3)[C@H](C)[C@H]12 | C(C)(C)N(CC)C(C)C.C(N)(=O)[C@H]1[N+](C[C@H](C1)S)(C)C.O[C@H](C)[C@@H]1[C@@H]2N(C(C([C@@H]2C)=O)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O.C(C)(C)N(CC)C(C)C.C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)Cl>>C(N)(=O)[C@H]1[N+](C[C@H](C1)SC=1[C@@H]([C@H]2N(C1C(=O)[O-])C([C@@H]2[C@@H](C)O)=O)C)(C)C | O=[N+]([O-])c1ccc(C[O:11][C:9]([CH:8]2[N:7]3[C:5](=[O:6])[C@H:4]([C@@H:2]([CH3:1])[OH:3])[C@H:26]3[C@@H:24]([CH3:25])[C:12]2=O)=[O:10])cc1.[SH:13][C@H:14]1[CH2:15][C@@H:16]([C:17]([NH2:18])=[O:19])[N+:20]([CH3:21])([CH3:22])[CH2:23]1>>[CH3:1][C@@H:2]([OH:3])[C@H:4]1[C:5](=[O:6])[N:7]2[C:8]([C:9](=[O:10])[O-:11])=[C:12]... | C[C@@H](O)[C@H]1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)C(=O)[C@H](C)[C@H]12.C[N+]1(C)C[C@@H](S)C[C@H]1C(N)=O | C[C@@H](O)[C@H]1C(=O)N2C(C(=O)[O-])=C(S[C@H]3C[C@@H](C(N)=O)[N+](C)(C)C3)[C@H](C)[C@H]12 | null | null | C(C)#N.[Pd].O1CCCC1.P(=O)([O-])([O-])[O-] | Functional Group Interconversion | OtherReaction | 27482b56caaab0dbeb237ee1c5dfb405982473c108933c0fa1fbfd7d74818f81 | a63e9c56d82c0b88ac489015e6c27fb1135e21cc36b2baa0877aa467e02113b8 | O=C1C[C@H]2CC(S[C@H]3CC[NH2+]C3)=CN12 | O=[C;H0;D3;+0:1]1-[C:2](-[C;D1;H3:3])-[C:4]2-[C:5]-[C:6](=[O;D1;H0:7])-[#7:8]-2-[CH;D3;+0:9]-1-[C:10](=[O;D1;H0:11])-[O;H0;D2;+0:12]-C-c1:c:c:c(-[N+](=O)-[O-]):c:c:1.[#7;+:13]-[C:14]-[C:15](-[SH;D1;+0:16])-[C:17]>>[#7;+:13]-[C:14]-[C:15](-[S;H0;D2;+0:16]-[C;H0;D3;+0:1]1=[C;H0;D3;+0:9](-[C:10](-[O-;H0;D1:12])=[O;D1;H0:1... | null | [] | null | null | 1 | HOUR | 0.20 ml of diisopropylethylamine and 0.24 ml of diphenylphosphoryl chloride were added dropwise, whilst ice-cooling, to a solution of 400 mg of 4-nitrobenzyl (1R, 5R, 6S)-6-[(1R)-1-hydroxyethyl]-1-methyl-2-oxo-1-carbapenam-3-carboxylate in 4 ml of dry acetonitrile, and the mixture was stirred at the same temperature fo... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Nitro group.Aliphatic thiol | Enamine.Monosulfide | c1ccccc1.C1C[C@@H]2CCN2C1 | C1=CN2CC[C@H]2C1 | C1=CN2CC[C@H]2C1.C1CC[NH+]C1 | HO- | C(C)#N.[Pd].O1CCCC1.P(=O)([O-])([O-])[O-] | null | 1 | C[C@@H](O)[C@H]1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)C(=O)[C@H](C)[C@H]12.C[N+]1(C)C[C@@H](S)C[C@H]1C(N)=O>C(C)#N.[Pd].O1CCCC1.P(=O)([O-])([O-])[O-]>C[C@@H](O)[C@H]1C(=O)N2C(C(=O)[O-])=C(S[C@H]3C[C@@H](C(N)=O)[N+](C)(C)C3)[C@H](C)[C@H]12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-75c6b588e2d943e48caad78f265c0a39 | C[C@@H](O)[C@H]1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)C(=O)C[C@H]12.C[N+]1(C)CC[C@H](S)C1>>C[C@@H](O)[C@H]1C(=O)N2C(C(=O)[O-])=C(S[C@H]3CC[N+](C)(C)C3)C[C@H]12 | C[N+]1(C[C@H](CC1)S)C.C(C)(C)N(CC)C(C)C.C(C)(C)N(CC)C(C)C.C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)Cl.O[C@H](C)[C@@H]1[C@@H]2N(C(C(C2)=O)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O>>C[N+]1(C[C@H](CC1)SC=1C[C@H]2N(C1C(=O)[O-])C([C@@H]2[C@@H](C)O)=O)C | O=[N+]([O-])c1ccc(C[O:11][C:9]([CH:8]2[N:7]3[C:5](=[O:6])[C@H:4]([C@@H:2]([CH3:1])[OH:3])[C@H:22]3[CH2:21][C:12]2=O)=[O:10])cc1.[SH:13][C@H:14]1[CH2:15][CH2:16][N+:17]([CH3:18])([CH3:19])[CH2:20]1>>[CH3:1][C@@H:2]([OH:3])[C@H:4]1[C:5](=[O:6])[N:7]2[C:8]([C:9](=[O:10])[O-:11])=[C:12]([S:13][C@H:14]3[CH2:15][CH2:16][N+:1... | C[C@@H](O)[C@H]1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)C(=O)C[C@H]12.C[N+]1(C)CC[C@H](S)C1 | C[C@@H](O)[C@H]1C(=O)N2C(C(=O)[O-])=C(S[C@H]3CC[N+](C)(C)C3)C[C@H]12 | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | 27482b56caaab0dbeb237ee1c5dfb405982473c108933c0fa1fbfd7d74818f81 | a63e9c56d82c0b88ac489015e6c27fb1135e21cc36b2baa0877aa467e02113b8 | O=C1C[C@H]2CC(S[C@H]3CC[NH2+]C3)=CN12 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]2-[C:4]-[C:5](=[O;D1;H0:6])-[#7:7]-2-[CH;D3;+0:8]-1-[C:9](=[O;D1;H0:10])-[O;H0;D2;+0:11]-C-c1:c:c:c(-[N+](=O)-[O-]):c:c:1.[#7;+:12]-[C:13]-[C:14](-[SH;D1;+0:15])-[C:16]>>[#7;+:12]-[C:13]-[C:14](-[S;H0;D2;+0:15]-[C;H0;D3;+0:1]1=[C;H0;D3;+0:8](-[C:9](-[O-;H0;D1:11])=[O;D1;H0:10])-[#7:7]2-[C:3... | 18.4 | [{"value": 18.4, "product": "C[N+]1(C[C@H](CC1)SC=1C[C@H]2N(C1C(=O)[O-])C([C@@H]2[C@@H](C)O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 183 μl of diisopropylethylamine and 218 μl of diphenylphosphoryl chloride were simultaneously added, whilst ice-cooling, to a solution of 348 mg of 4-nitrobenzyl (5R, 6S)-6-[(1R)-1-hydroxyethyl]-2-oxo-1-carbapenam-3-carboxylate dissolved in 4 ml of dry acetonitrile and the mixture was stirred at the same temperature fo... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Nitro group.Aliphatic thiol | Enamine.Monosulfide | c1ccccc1.C1C[C@@H]2CCN2C1 | C1=CN2CC[C@H]2C1 | C1=CN2CC[C@H]2C1.C1CC[NH+]C1 | HO- | C(C)#N | null | 1 | C[C@@H](O)[C@H]1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)C(=O)C[C@H]12.C[N+]1(C)CC[C@H](S)C1>C(C)#N>C[C@@H](O)[C@H]1C(=O)N2C(C(=O)[O-])=C(S[C@H]3CC[N+](C)(C)C3)C[C@H]12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c134e3f71f3f457ca6e219a28a76ce5e | CC[N+]1(C)C[C@@H](S)C[C@H]1C(=O)N(C)C.C[C@@H](O)[C@H]1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)C(=O)C[C@H]12>>CC[N+]1(C)C[C@@H](SC2=C(C(=O)[O-])N3C(=O)[C@H]([C@@H](C)O)[C@H]3C2)C[C@H]1C(=O)N(C)C | O[C@H](C)[C@@H]1[C@@H]2N(C(C(C2)=O)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O.CN(C(=O)[C@H]1[N+](C[C@H](C1)S)(C)CC)C>>C(C)[N+]1([C@@H](C[C@@H](C1)SC=1C[C@H]2N(C1C(=O)[O-])C([C@@H]2[C@@H](C)O)=O)C(N(C)C)=O)C | [CH3:1][CH2:2][N+:3]1([CH3:4])[CH2:5][C@@H:6]([SH:7])[CH2:22][C@H:23]1[C:24](=[O:25])[N:26]([CH3:27])[CH3:28].O=[N+]([O-])c1ccc(C[O:12][C:10]([CH:9]2[C:8](=O)[CH2:21][C@H:20]3[N:13]2[C:14](=[O:15])[C@@H:16]3[C@@H:17]([CH3:18])[OH:19])=[O:11])cc1>>[CH3:1][CH2:2][N+:3]1([CH3:4])[CH2:5][C@@H:6]([S:7][C:8]2=[C:9]([C:10](=[... | CC[N+]1(C)C[C@@H](S)C[C@H]1C(=O)N(C)C.C[C@@H](O)[C@H]1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)C(=O)C[C@H]12 | CC[N+]1(C)C[C@@H](SC2=C(C(=O)[O-])N3C(=O)[C@H]([C@@H](C)O)[C@H]3C2)C[C@H]1C(=O)N(C)C | null | null | null | Functional Group Interconversion | OtherReaction | 27482b56caaab0dbeb237ee1c5dfb405982473c108933c0fa1fbfd7d74818f81 | a63e9c56d82c0b88ac489015e6c27fb1135e21cc36b2baa0877aa467e02113b8 | O=C1C[C@H]2CC(S[C@H]3CC[NH2+]C3)=CN12 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]2-[C:4]-[C:5](=[O;D1;H0:6])-[#7:7]-2-[CH;D3;+0:8]-1-[C:9](=[O;D1;H0:10])-[O;H0;D2;+0:11]-C-c1:c:c:c(-[N+](=O)-[O-]):c:c:1.[#7;+:12]-[C:13]-[C:14](-[SH;D1;+0:15])-[C:16]>>[#7;+:12]-[C:13]-[C:14](-[S;H0;D2;+0:15]-[C;H0;D3;+0:1]1=[C;H0;D3;+0:8](-[C:9](-[O-;H0;D1:11])=[O;D1;H0:10])-[#7:7]2-[C:5... | 10.1 | [{"value": 10.1, "product": "C(C)[N+]1([C@@H](C[C@@H](C1)SC=1C[C@H]2N(C1C(=O)[O-])C([C@@H]2[C@@H](C)O)=O)C(N(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following a procedure similar to that described in Example 6, but using 459 mg of 4-nitrobenzyl (5R, 6S)-6-[(1R)-1-hydroxyethyl]-2-oxo-1-carbapenam-3-carboxylate and 580 mg of the crude (2S, 4S)-2-(N,N-dimethylcarbamoyl)-1-ethyl-1-methyl-4-mercaptopyrrolidinium salt [prepared as described in Example 9-(2)], 55 mg of th... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Nitro group.Aliphatic thiol | Enamine.Monosulfide | c1ccccc1.C1C[C@@H]2CCN2C1 | C1=CN2CC[C@H]2C1 | C1CC[NH+]C1.C1=CN2CC[C@H]2C1 | HO- | null | null | null | CC[N+]1(C)C[C@@H](S)C[C@H]1C(=O)N(C)C.C[C@@H](O)[C@H]1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)C(=O)C[C@H]12>>CC[N+]1(C)C[C@@H](SC2=C(C(=O)[O-])N3C(=O)[C@H]([C@@H](C)O)[C@H]3C2)C[C@H]1C(=O)N(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d999c5bb11f24db2a6563430a9eb42c7 | CN(C)C(=O)[C@@H]1C[C@H](S)C[N+]1(C)C.C[C@@H](O)[C@H]1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)C(=O)C[C@H]12>>C[C@@H](O)[C@H]1C(=O)N2C(C(=O)[O-])=C(S[C@H]3C[C@@H](C(=O)N(C)C)[N+](C)(C)C3)C[C@H]12 | CN(C(=O)[C@H]1[N+](C[C@H](C1)S)(C)C)C.[Cl-].O[C@H](C)[C@@H]1[C@@H]2N(C(C(C2)=O)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O>>C[N+]1([C@@H](C[C@@H](C1)SC=1C[C@H]2N(C1C(=O)[O-])C([C@@H]2[C@@H](C)O)=O)C(N(C)C)=O)C | [SH:13][C@H:14]1[CH2:15][C@@H:16]([C:17](=[O:18])[N:19]([CH3:20])[CH3:21])[N+:22]([CH3:23])([CH3:24])[CH2:25]1.O=[N+]([O-])c1ccc(C[O:11][C:9]([CH:8]2[N:7]3[C:5](=[O:6])[C@H:4]([C@@H:2]([CH3:1])[OH:3])[C@H:27]3[CH2:26][C:12]2=O)=[O:10])cc1>>[CH3:1][C@@H:2]([OH:3])[C@H:4]1[C:5](=[O:6])[N:7]2[C:8]([C:9](=[O:10])[O-:11])=[... | CN(C)C(=O)[C@@H]1C[C@H](S)C[N+]1(C)C.C[C@@H](O)[C@H]1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)C(=O)C[C@H]12 | C[C@@H](O)[C@H]1C(=O)N2C(C(=O)[O-])=C(S[C@H]3C[C@@H](C(=O)N(C)C)[N+](C)(C)C3)C[C@H]12 | null | null | C(C)#N.C(C)(C)N(CC)C(C)C.P(=O)([O-])([O-])[O-].[Pd].O1CCCC1 | Functional Group Interconversion | OtherReaction | 27482b56caaab0dbeb237ee1c5dfb405982473c108933c0fa1fbfd7d74818f81 | a63e9c56d82c0b88ac489015e6c27fb1135e21cc36b2baa0877aa467e02113b8 | O=C1C[C@H]2CC(S[C@H]3CC[NH2+]C3)=CN12 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]2-[C:4]-[C:5](=[O;D1;H0:6])-[#7:7]-2-[CH;D3;+0:8]-1-[C:9](=[O;D1;H0:10])-[O;H0;D2;+0:11]-C-c1:c:c:c(-[N+](=O)-[O-]):c:c:1.[#7;+:12]-[C:13]-[C:14](-[SH;D1;+0:15])-[C:16]>>[#7;+:12]-[C:13]-[C:14](-[S;H0;D2;+0:15]-[C;H0;D3;+0:1]1=[C;H0;D3;+0:8](-[C:9](-[O-;H0;D1:11])=[O;D1;H0:10])-[#7:7]2-[C:3... | 22.5 | [{"value": 22.5, "product": "C[N+]1([C@@H](C[C@@H](C1)SC=1C[C@H]2N(C1C(=O)[O-])C([C@@H]2[C@@H](C)O)=O)C(N(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 126 μl of diisopropylethylamine and 132 μl of diphenylphophoryl chloride were simultaneously added, whilst ice-cooling, to a solution of 218 mg of 4-nitrobenzyl (5R, 6S)-6-[(1R)-1-hydroxyethyl]-2-oxo-1-carbapenam-3-carboxylate dissolved in 3 ml of dry acetonitrile, and the mixture was stirred at the same temperature fo... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Nitro group.Aliphatic thiol | Enamine.Monosulfide | c1ccccc1.C1C[C@@H]2CCN2C1 | C1=CN2CC[C@H]2C1 | C1=CN2CC[C@H]2C1.C1CC[NH+]C1 | HO- | C(C)#N.C(C)(C)N(CC)C(C)C.P(=O)([O-])([O-])[O-].[Pd].O1CCCC1 | null | 1 | CN(C)C(=O)[C@@H]1C[C@H](S)C[N+]1(C)C.C[C@@H](O)[C@H]1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)C(=O)C[C@H]12>C(C)#N.C(C)(C)N(CC)C(C)C.P(=O)([O-])([O-])[O-].[Pd].O1CCCC1>C[C@@H](O)[C@H]1C(=O)N2C(C(=O)[O-])=C(S[C@H]3C[C@@H](C(=O)N(C)C)[N+](C)(C)C3)C[C@H]12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-86a7cfd3b625462386fd3ee3e7adacc5 | C[C@@H](O)[C@H]1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)C(=O)C[C@H]12.C[N+]1(C)C[C@@H](S)C[C@H]1C(N)=O>>C[C@@H](O)[C@H]1C(=O)N2C(C(=O)[O-])=C(S[C@H]3C[C@@H](C(N)=O)[N+](C)(C)C3)C[C@H]12 | C(N)(=O)[C@H]1[N+](C[C@H](C1)S)(C)C.C(C)(C)N(CC)C(C)C.C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)Cl.O[C@H](C)[C@@H]1[C@@H]2N(C(C(C2)=O)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O>>C(N)(=O)[C@H]1[N+](C[C@H](C1)SC=1C[C@H]2N(C1C(=O)[O-])C([C@@H]2[C@@H](C)O)=O)(C)C | O=[N+]([O-])c1ccc(C[O:11][C:9]([CH:8]2[N:7]3[C:5](=[O:6])[C@H:4]([C@@H:2]([CH3:1])[OH:3])[C@H:25]3[CH2:24][C:12]2=O)=[O:10])cc1.[SH:13][C@H:14]1[CH2:15][C@@H:16]([C:17]([NH2:18])=[O:19])[N+:20]([CH3:21])([CH3:22])[CH2:23]1>>[CH3:1][C@@H:2]([OH:3])[C@H:4]1[C:5](=[O:6])[N:7]2[C:8]([C:9](=[O:10])[O-:11])=[C:12]([S:13][C@H... | C[C@@H](O)[C@H]1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)C(=O)C[C@H]12.C[N+]1(C)C[C@@H](S)C[C@H]1C(N)=O | C[C@@H](O)[C@H]1C(=O)N2C(C(=O)[O-])=C(S[C@H]3C[C@@H](C(N)=O)[N+](C)(C)C3)C[C@H]12 | null | null | C(C)#N.C(C)OCC | Functional Group Interconversion | OtherReaction | 27482b56caaab0dbeb237ee1c5dfb405982473c108933c0fa1fbfd7d74818f81 | a63e9c56d82c0b88ac489015e6c27fb1135e21cc36b2baa0877aa467e02113b8 | O=C1C[C@H]2CC(S[C@H]3CC[NH2+]C3)=CN12 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]2-[C:4]-[C:5](=[O;D1;H0:6])-[#7:7]-2-[CH;D3;+0:8]-1-[C:9](=[O;D1;H0:10])-[O;H0;D2;+0:11]-C-c1:c:c:c(-[N+](=O)-[O-]):c:c:1.[#7;+:12]-[C:13]-[C:14](-[SH;D1;+0:15])-[C:16]>>[#7;+:12]-[C:13]-[C:14](-[S;H0;D2;+0:15]-[C;H0;D3;+0:1]1=[C;H0;D3;+0:8](-[C:9](-[O-;H0;D1:11])=[O;D1;H0:10])-[#7:7]2-[C:3... | null | [] | null | null | 1 | HOUR | 210 μl of diisopropylethylamine and 250 μl of diphenylphosphoryl chloride were simultaneously added, whilst ice-cooling, to a solution of 400 mg of 4-nitrobenzyl (5R, 6S)-6-[(1R)-1-hydroxyethyl]-2-oxo-1-carbapenam-3-carboxylate dissolved in 5 ml of dry acetronitrile, and the mixture was stirred for 1 hour, whilst ice-c... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Nitro group.Aliphatic thiol | Enamine.Monosulfide | c1ccccc1.C1C[C@@H]2CCN2C1 | C1=CN2CC[C@H]2C1 | C1=CN2CC[C@H]2C1.C1CC[NH+]C1 | HO- | C(C)#N.C(C)OCC | null | 1 | C[C@@H](O)[C@H]1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)C(=O)C[C@H]12.C[N+]1(C)C[C@@H](S)C[C@H]1C(N)=O>C(C)#N.C(C)OCC>C[C@@H](O)[C@H]1C(=O)N2C(C(=O)[O-])=C(S[C@H]3C[C@@H](C(N)=O)[N+](C)(C)C3)C[C@H]12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d17197b3300b4c588249b50f58b34560 | C[C@@H](O)[C@H]1C(=O)N2C(C(=O)[O-])=C(SC3CCNC3=O)[C@H](C)[C@H]12.Cc1oc(=O)oc1CI>>Cc1oc(=O)oc1COC(=O)C1=C(SC2CCNC2=O)[C@H](C)[C@@H]2[C@@H]([C@@H](C)O)C(=O)N12 | CC1=C(OC(O1)=O)CI.O=C1NCCC1SC=1[C@@H]([C@H]2N(C1C(=O)[O-])C([C@@H]2[C@@H](C)O)=O)C.[Na+].CN(C=O)C>>O=C1NCCC1SC=1[C@@H]([C@H]2N(C1C(=O)OCC=1OC(OC1C)=O)C([C@@H]2[C@@H](C)O)=O)C | [O-:9][C:10](=[O:11])[C:12]1=[C:13]([S:14][CH:15]2[CH2:16][CH2:17][NH:18][C:19]2=[O:20])[C@H:21]([CH3:22])[C@@H:23]2[C@@H:24]([C@@H:25]([CH3:26])[OH:27])[C:28](=[O:29])[N:30]12.I[CH2:8][c:7]1[c:2]([CH3:1])[o:3][c:4](=[O:5])[o:6]1>>[CH3:1][c:2]1[o:3][c:4](=[O:5])[o:6][c:7]1[CH2:8][O:9][C:10](=[O:11])[C:12]1=[C:13]([S:14... | C[C@@H](O)[C@H]1C(=O)N2C(C(=O)[O-])=C(SC3CCNC3=O)[C@H](C)[C@H]12.Cc1oc(=O)oc1CI | Cc1oc(=O)oc1COC(=O)C1=C(SC2CCNC2=O)[C@H](C)[C@@H]2[C@@H]([C@@H](C)O)C(=O)N12 | null | null | C(Cl)(Cl)Cl.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | c07f6f64ff82321b3607467d1ee707cb9bab7ac0cd7c3098b7f6ee7c8546417e | 670c5cfed3b5aa12e0b1c180fc6f2dc23f2114806bdb54cf3b29925a677cc9b5 | O=C(OCc1coc(=O)o1)C1=C(SC2CCNC2=O)C[C@@H]2CC(=O)N12 | I-[CH2;D2;+0:1]-[c:2]1:[#8;a:3]:[c:4]:[#8;a:5]:[c:6]:1-[C;D1;H3:7].[#16:8]-[C:9](=[C:10](-[C:11](-[O-;H0;D1:12])=[O;D1;H0:13])-[#7:14]-[C:15]=[O;D1;H0:16])-[C:17]>>[#16:8]-[C:9](=[C:10](-[C:11](=[O;D1;H0:13])-[O;H0;D2;+0:12]-[CH2;D2;+0:1]-[c:2]1:[#8;a:3]:[c:4]:[#8;a:5]:[c:6]:1-[C;D1;H3:7])-[#7:14]-[C:15]=[O;D1;H0:16])-... | 45.7 | [{"value": 45.7, "product": "O=C1NCCC1SC=1[C@@H]([C@H]2N(C1C(=O)OCC=1OC(OC1C)=O)C([C@@H]2[C@@H](C)O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 80 | MINUTE | A solution of 66 mg of 5-methyl-2-oxo-1,3-dioxolen-4-ylmethyl iodide (prepared by heating 5-methyl-2-oxo-1,3-dioxolen-4-ylmethyl bromide and sodium iodide under reflux in acetone) in chloroform was added to a mixture of 47.6 mg of sodium (1R, 5S, 6S)-2-(2-oxo-3-pyrrolidinylthio)-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carba... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Ester | null | null | c1coco1.C1CCNC1.C1=CN2CC[C@H]2C1 | I- | C(Cl)(Cl)Cl.C(C)(=O)OCC | null | 1.333333 | C[C@@H](O)[C@H]1C(=O)N2C(C(=O)[O-])=C(SC3CCNC3=O)[C@H](C)[C@H]12.Cc1oc(=O)oc1CI>C(Cl)(Cl)Cl.C(C)(=O)OCC>Cc1oc(=O)oc1COC(=O)C1=C(SC2CCNC2=O)[C@H](C)[C@@H]2[C@@H]([C@@H](C)O)C(=O)N12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3eda79cd98774b5c872c62570bbbdb00 | CC(I)OC(=O)OC1CCCCC1.CC1C(SC2CNC(=O)C2)=C(C(=O)[O-])N2C(=O)C([C@@H](C)O)[C@@H]12>>CC(OC(=O)OC1CCCCC1)OC(=O)C1=C(SC2CNC(=O)C2)[C@H](C)[C@@H]2[C@@H]([C@@H](C)O)C(=O)N12 | O=C1NCC(C1)SC=1C([C@H]2N(C1C(=O)[O-])C(C2[C@@H](C)O)=O)C.[Na+].C1(CCCCC1)OC(=O)OC(C)I>>O=C1NCC(C1)SC=1[C@@H]([C@H]2N(C1C(=O)OC(C)OC(=O)OC1CCCCC1)C([C@@H]2[C@@H](C)O)=O)C | I[CH:2]([CH3:1])[O:3][C:4](=[O:5])[O:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1.[O-:13][C:14](=[O:15])[C:16]1=[C:17]([S:18][CH:19]2[CH2:20][NH:21][C:22](=[O:23])[CH2:24]2)[CH:25]([CH3:26])[C@@H:27]2[CH:28]([C@@H:29]([CH3:30])[OH:31])[C:32](=[O:33])[N:34]12>>[CH3:1][CH:2]([O:3][C:4](=[O:5])[O:6][CH:7]1[CH2:8][CH2:... | CC(I)OC(=O)OC1CCCCC1.CC1C(SC2CNC(=O)C2)=C(C(=O)[O-])N2C(=O)C([C@@H](C)O)[C@@H]12 | CC(OC(=O)OC1CCCCC1)OC(=O)C1=C(SC2CNC(=O)C2)[C@H](C)[C@@H]2[C@@H]([C@@H](C)O)C(=O)N12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 325232c11a00d4b4ffa64d80925dcb5ba322ee1152974e63432458179bde8125 | 218bc40d86dd35ef0e94658f95ea11dc9d21baab063ffc4b6241b0e1ab8da5fa | O=C1CC(SC2=C(C(=O)OCOC(=O)OC3CCCCC3)N3C(=O)C[C@H]3C2)CN1 | I-[CH;D3;+0:1](-[C;D1;H3:2])-[#8:3]-[C:4](-[#8:5])=[O;D1;H0:6].[#16:7]-[C:8](=[C:9](-[C:10](-[O-;H0;D1:11])=[O;D1;H0:12])-[#7:13]-[C:14]=[O;D1;H0:15])-[C:16]>>[#16:7]-[C:8](=[C:9](-[C:10](=[O;D1;H0:12])-[O;H0;D2;+0:11]-[CH;D3;+0:1](-[C;D1;H3:2])-[#8:3]-[C:4](-[#8:5])=[O;D1;H0:6])-[#7:13]-[C:14]=[O;D1;H0:15])-[C:16] | null | [] | null | null | null | null | Following a procedure similar to that described in Example 39, but using 54 mg of sodium 2-(2-oxo-4-pyrrolidinylthio)-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate obtained by a similar procedure to that described in Example 36 and 50 μl of 1-(cyclohexyloxycarbonyloxy)ethyl iodide, 62 mg of the title c... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Carbonic Ester | Carbonic Ester.Ester | null | null | C1CCCCC1.C1CCNC1.C1=CN2CC[C@H]2C1 | I- | null | null | null | CC(I)OC(=O)OC1CCCCC1.CC1C(SC2CNC(=O)C2)=C(C(=O)[O-])N2C(=O)C([C@@H](C)O)[C@@H]12>>CC(OC(=O)OC1CCCCC1)OC(=O)C1=C(SC2CNC(=O)C2)[C@H](C)[C@@H]2[C@@H]([C@@H](C)O)C(=O)N12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-50ea5bd8d6b3424b8c861a6db968fd72 | CC1C(SC2CNC(=O)C2)=C(C(=O)[O-])N2C(=O)C([C@@H](C)O)[C@@H]12.Cc1oc(=O)oc1CBr>>Cc1oc(=O)oc1COC(=O)C1=C(SC2CNC(=O)C2)[C@H](C)[C@@H]2[C@@H]([C@@H](C)O)C(=O)N12 | O=C1NCC(C1)SC=1C([C@H]2N(C1C(=O)[O-])C(C2[C@@H](C)O)=O)C.[Na+].CC1=C(OC(O1)=O)CBr>>O=C1NCC(C1)SC=1[C@@H]([C@H]2N(C1C(=O)OCC=1OC(OC1C)=O)C([C@@H]2[C@@H](C)O)=O)C | [O-:9][C:10](=[O:11])[C:12]1=[C:13]([S:14][CH:15]2[CH2:16][NH:17][C:18](=[O:19])[CH2:20]2)[CH:21]([CH3:22])[C@@H:23]2[CH:24]([C@@H:25]([CH3:26])[OH:27])[C:28](=[O:29])[N:30]12.Br[CH2:8][c:7]1[c:2]([CH3:1])[o:3][c:4](=[O:5])[o:6]1>>[CH3:1][c:2]1[o:3][c:4](=[O:5])[o:6][c:7]1[CH2:8][O:9][C:10](=[O:11])[C:12]1=[C:13]([S:14... | CC1C(SC2CNC(=O)C2)=C(C(=O)[O-])N2C(=O)C([C@@H](C)O)[C@@H]12.Cc1oc(=O)oc1CBr | Cc1oc(=O)oc1COC(=O)C1=C(SC2CNC(=O)C2)[C@H](C)[C@@H]2[C@@H]([C@@H](C)O)C(=O)N12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c07f6f64ff82321b3607467d1ee707cb9bab7ac0cd7c3098b7f6ee7c8546417e | 670c5cfed3b5aa12e0b1c180fc6f2dc23f2114806bdb54cf3b29925a677cc9b5 | O=C1CC(SC2=C(C(=O)OCc3coc(=O)o3)N3C(=O)C[C@H]3C2)CN1 | Br-[CH2;D2;+0:1]-[c:2]1:[#8;a:3]:[c:4]:[#8;a:5]:[c:6]:1-[C;D1;H3:7].[#16:8]-[C:9](=[C:10](-[C:11](-[O-;H0;D1:12])=[O;D1;H0:13])-[#7:14]-[C:15]=[O;D1;H0:16])-[C:17]>>[#16:8]-[C:9](=[C:10](-[C:11](=[O;D1;H0:13])-[O;H0;D2;+0:12]-[CH2;D2;+0:1]-[c:2]1:[#8;a:3]:[c:4]:[#8;a:5]:[c:6]:1-[C;D1;H3:7])-[#7:14]-[C:15]=[O;D1;H0:16])... | 79.5 | [{"value": 79.5, "product": "O=C1NCC(C1)SC=1[C@@H]([C@H]2N(C1C(=O)OCC=1OC(OC1C)=O)C([C@@H]2[C@@H](C)O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following a procedure similar to that described in Example 39, but using 50 mg of sodium 2-(2-oxo-4-pyrrolidinylthio)-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate and 55 mg of 5-methyl-2-oxo-1,3-dioxolen-4-ylmethyl bromide, 50 mg of the title compound were obtained as a colorless powder.
Conditions: S... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Ester | null | null | c1coco1.C1CCNC1.C1=CN2CC[C@H]2C1 | Br- | null | null | null | CC1C(SC2CNC(=O)C2)=C(C(=O)[O-])N2C(=O)C([C@@H](C)O)[C@@H]12.Cc1oc(=O)oc1CBr>>Cc1oc(=O)oc1COC(=O)C1=C(SC2CNC(=O)C2)[C@H](C)[C@@H]2[C@@H]([C@@H](C)O)C(=O)N12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9c98a215df3b4044bafe556b8b6a43bb | CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(=O)O.[NH4+]>>CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(N)=O | [Cl-].[NH4+].C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)O)C(=O)O.ClC(=O)OCC.[OH-].[NH4+]>>C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)O)C(N)=O | O[C:14]([C@H:13]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][C@H:10]([OH:11])[CH2:12]1)=[O:16].[NH4+:15]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][C@H:10]([OH:11])[CH2:12][C@H:13]1[C:14]([NH2:15])=[O:16] | CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(=O)O.[NH4+] | CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(N)=O | null | null | O1CCCC1.C(C)N(CC)CC | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | C1CCNC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C:13].[NH4+;D0:14]>>[C:4]-[C:3](-[C;H0;D3;+0:1](-[NH2;D1;+0:14])=[O;D1;H0:2])-[#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] | null | [] | null | null | 35 | MINUTE | 58 g of (2S, 4R)-1-(t-butoxycarbonyl)-4-hydroxy-2-pyrrolidinecarboxylic acid [prepared as described in step (1) aboveπ were dissolved in 850 ml of dry tetrahydrofuran, and then 38.2 ml of triethylamine were added to the mixture at -15° to -20° C. A solution of 26.3 ml of ethyl chloroformate in 240 ml of dry tetrahydrof... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | C1CC[NH]C1 | HO- | O1CCCC1.C(C)N(CC)CC | null | 0.583333 | CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(=O)O.[NH4+]>O1CCCC1.C(C)N(CC)CC>CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(N)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2a56e9a0f2494ea49832784e8b43d622 | CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(N)=O.CS(=O)(=O)Cl>>CC(C)(C)OC(=O)N1C[C@H](OS(C)(=O)=O)C[C@H]1C(N)=O | [Cl-].[Na+].CS(=O)(=O)Cl.C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)O)C(N)=O.C(C)N(CC)CC>>C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)OS(=O)(=O)C)C(N)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][C@H:10]([OH:11])[CH2:16][C@H:17]1[C:18]([NH2:19])=[O:20].Cl[S:12]([CH3:13])(=[O:14])=[O:15]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][C@H:10]([O:11][S:12]([CH3:13])(=[O:14])=[O:15])[CH2:16][C@H:17]1[C:18]([NH2:19])=[O:20] | CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(N)=O.CS(=O)(=O)Cl | CC(C)(C)OC(=O)N1C[C@H](OS(C)(=O)=O)C[C@H]1C(N)=O | null | null | O1CCCC1 | Acylation | Formation of Sulfonic Esters | 641955d0081c80f158ce2aacd31873a3f3301c87ca0800cf263e288ba8390217 | 4f9373df8a11470603daf885a5777cebf95940370e32739263d35df0f171a0dd | C1CCNC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#7:5]-[C:6]-[C:7](-[OH;D1;+0:8])-[C:9]>>[#7:5]-[C:6]-[C:7](-[O;H0;D2;+0:8]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])-[C:9] | null | [] | null | null | 1 | HOUR | 1.85 ml of methanesulfonyl chloride was added, whilst ice-cooling, to a solution of 5.0 g of (2S, 4R)-1-(t-butoxycarbonyl)-2-carbamoyl-4-hydroxypyrrolidine [prepared as described in step (2) above] in 250 ml of dry tetrahydrofuran, followed by 3.31 ml of triethylamine. The mixture was then stirred at 0° to 5° C. for 1 ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Sulfonyl halide | Mesylate | null | null | C1CC[NH]C1 | HCl | O1CCCC1 | null | 1 | CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(N)=O.CS(=O)(=O)Cl>O1CCCC1>CC(C)(C)OC(=O)N1C[C@H](OS(C)(=O)=O)C[C@H]1C(N)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5a57398a5c504dffb529c848afe88765 | COc1ccc(CS[C@H]2C[C@@H](C(N)=O)N(C(=O)OC(C)(C)C)C2)cc1>>COc1ccc(CS[C@@H]2CN[C@H](C(N)=O)C2)cc1 | C([O-])(O)=O.[Na+].O1CCOCC1.Cl.C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(N)=O>>C(N)(=O)[C@H]1NC[C@H](C1)SCC1=CC=C(C=C1)OC | CC(C)(C)OC(=O)[N:11]1[CH2:10][C@@H:9]([S:8][CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:18][cH:17]2)[CH2:16][C@H:12]1[C:13]([NH2:14])=[O:15]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][C@@H:9]2[CH2:10][NH:11][C@H:12]([C:13]([NH2:14])=[O:15])[CH2:16]2)[cH:17][cH:18]1 | COc1ccc(CS[C@H]2C[C@@H](C(N)=O)N(C(=O)OC(C)(C)C)C2)cc1 | COc1ccc(CS[C@@H]2CN[C@H](C(N)=O)C2)cc1 | null | null | C(C)(=O)OCC | Reduction | Boc amine deprotection | 7b506000be0005f6be41b2386b5bd6a8c45f704baa22d692d2f2ec984758e4ad | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(CS[C@H]2CCNC2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1-[C:6](-[N;D1;H2:7])=[O;D1;H0:8]>>[N;D1;H2:7]-[C:6](=[O;D1;H0:8])-[C:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | 97.5 | [{"value": 97.5, "product": "C(N)(=O)[C@H]1NC[C@H](C1)SCC1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 1.92 g of (2S, 4S)-1-(t-butoxycarbonyl)-2-carbamoyl-4-(4-methoxybenzylthio)pyrrolidine [prepared as described in step (4) above] was dissolved in 25 ml of ethyl acetate, and 26.2 ml of a 4N dioxane solution of hydrogen chloride were added to the solution, whilst ice-cooling. The mixture was then stirred at 0° to 5° C. ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]C1 | C1CCNC1 | c1ccccc1.C1CCNC1 | HO- | C(C)(=O)OCC | null | 0.5 | COc1ccc(CS[C@H]2C[C@@H](C(N)=O)N(C(=O)OC(C)(C)C)C2)cc1>C(C)(=O)OCC>COc1ccc(CS[C@@H]2CN[C@H](C(N)=O)C2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-744e3ebab8024cf1ac0a111f766472de | CI.COc1ccc(CS[C@@H]2CN[C@H](C(N)=O)C2)cc1>>COc1cccc(CS[C@H]2C[C@@H](C(N)=O)N(C)C2)c1 | CI.C(N)(=O)[C@H]1NC[C@H](C1)SCC1=CC=C(C=C1)OC.C([O-])(O)=O.[Na+]>>C(N)(=O)[C@H]1N(C[C@H](C1)SCC1=CC(=CC=C1)OC)C | I[CH3:17].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:7]([CH2:8][S:9][C@H:10]2[CH2:11][C@@H:12]([C:13]([NH2:14])=[O:15])[NH:16][CH2:18]2)[cH:6][cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][S:9][C@H:10]2[CH2:11][C@@H:12]([C:13]([NH2:14])=[O:15])[N:16]([CH3:17])[CH2:18]2)[cH:19]1 | CI.COc1ccc(CS[C@@H]2CN[C@H](C(N)=O)C2)cc1 | COc1cccc(CS[C@H]2C[C@@H](C(N)=O)N(C)C2)c1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 20c478f89acadf18c05fe55710d5089bb28acd53605cdd5c25fd32cb95bbd77b | 7cc25fba33369069673bac5bd8fc404dc064da8d6c8cf4a77f21f4df0a617fe3 | c1ccc(CS[C@H]2CCNC2)cc1 | I-[CH3;D1;+0:1].[#8:2]-[c:3]1:[c:4]:[cH;D2;+0:5]:[c;H0;D3;+0:6](-[C:7]-[#16:8]-[C:9]2-[C:10]-[C:11](-[C:12](-[N;D1;H2:13])=[O;D1;H0:14])-[NH;D2;+0:15]-[C:16]-2):[cH;D2;+0:17]:[cH;D2;+0:18]:1>>[#8:2]-[c:3]1:[c:4]:[cH;D2;+0:5]:[cH;D2;+0:17]:[c;H0;D3;+0:6](-[C:7]-[#16:8]-[C:9]2-[C:10]-[C:11](-[C:12](-[N;D1;H2:13])=[O;D1;H... | null | [] | null | null | 20 | MINUTE | 0.07 ml of methyl iodide was added, whilst ice-cooling, to a solution of 0.6 g of (2S, 4S)-2-carbamoyl-4-(4-methoxybenzylthio)pyrrolidine [prepared as described in step (5) above] dissolved in 4.5 ml of dry dimethylformamide. The mixture was then stirred at 0° to 5° C. for 5 minutes and at room temperature for 20 minut... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | c1ccccc1.C1CCNC1 | c1ccccc1.C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HI | CN(C=O)C | null | 0.333333 | CI.COc1ccc(CS[C@@H]2CN[C@H](C(N)=O)C2)cc1>CN(C=O)C>COc1cccc(CS[C@H]2C[C@@H](C(N)=O)N(C)C2)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-968f75398c654623b4623e870b77110f | COc1ccc(CS[C@@H]2CN[C@H](C(N)=O)C2)cc1.FCCBr>>COc1ccc(CS[C@H]2C[C@@H](C(N)=O)N(CCF)C2)cc1 | BrCCF.[I-].[Na+].C([O-])(O)=O.[Na+].C(N)(=O)[C@H]1NC[C@H](C1)SCC1=CC=C(C=C1)OC.C([O-])(O)=O.[Na+]>>C(N)(=O)[C@H]1N(C[C@H](C1)SCC1=CC=C(C=C1)OC)CCF | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][C@H:9]2[CH2:10][C@@H:11]([C:12]([NH2:13])=[O:14])[NH:15][CH2:19]2)[cH:20][cH:21]1.Br[CH2:16][CH2:17][F:18]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][C@H:9]2[CH2:10][C@@H:11]([C:12]([NH2:13])=[O:14])[N:15]([CH2:16][CH2:17][F:18])[CH2:19]2)[cH:20][cH:21]1 | COc1ccc(CS[C@@H]2CN[C@H](C(N)=O)C2)cc1.FCCBr | COc1ccc(CS[C@H]2C[C@@H](C(N)=O)N(CCF)C2)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 19b442dc26882f89f7423416f5e0a16bdb8e48776df57991434a0634e21f0505 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CS[C@H]2CCNC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[F;D1;H0:3].[N;D1;H2:4]-[C:5](=[O;D1;H0:6])-[C:7]1-[C:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[F;D1;H0:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[C:8]-[C:7]-1-[C:5](-[N;D1;H2:4])=[O;D1;H0:6] | null | [] | null | null | 20 | MINUTE | 0.4 ml of 1-bromo-2-fluoroethane, 3.83 g of sodium iodide and 0.38 g of sodium bicarbonate were added to a solution of 1.2 g of (2S, 4S)-2-carbamoyl-4-(4-methoxybenzylthio)pyrrolidine dissolved in 12 ml of dry dimethylformamide, whilst ice-cooling, and the mixture was stirred at room temperature for 20 minutes and then... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HBr | CN(C=O)C | null | 0.333333 | COc1ccc(CS[C@@H]2CN[C@H](C(N)=O)C2)cc1.FCCBr>CN(C=O)C>COc1ccc(CS[C@H]2C[C@@H](C(N)=O)N(CCF)C2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4d674adf922840e691348acf82353519 | CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(=O)O.CN>>CNC(=O)[C@@H]1C[C@@H](O)CN1C(=O)OC(C)(C)C | [Cl-].[Na+].C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)O)C(=O)O.ClC(=O)OCC.CN>>C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)O)C(NC)=O | O[C:3](=[O:4])[C@@H:5]1[CH2:6][C@@H:7]([OH:8])[CH2:9][N:10]1[C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17].[CH3:1][NH2:2]>>[CH3:1][NH:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@@H:7]([OH:8])[CH2:9][N:10]1[C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17] | CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(=O)O.CN | CNC(=O)[C@@H]1C[C@@H](O)CN1C(=O)OC(C)(C)C | null | null | O1CCCC1.C(C)N(CC)CC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | C1CCNC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C:13].[C;D1;H3:14]-[NH2;D1;+0:15]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:15]-[C;D1;H3:14])-[#7:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])... | null | [] | null | null | 1 | HOUR | 9.91 ml of triethylamine were added at -40° C. to a solution of 15.03 g of (2S, 4R)-1-(t-butoxycarbonyl)-4-hydroxy-2-pyrrolidinecarboxylic acid dissolved in 250 ml of dry tetrahydrofuran, and then a solution of 6.81 ml of ethyl chloroformate in 30 ml of dry tetrahydrofuran was added at -30° to -40° C. to the resulting ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CC[NH]C1 | HO- | O1CCCC1.C(C)N(CC)CC | null | 1 | CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(=O)O.CN>O1CCCC1.C(C)N(CC)CC>CNC(=O)[C@@H]1C[C@@H](O)CN1C(=O)OC(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2785b6e61574455283939136e0ff5801 | CNC(=O)[C@@H]1C[C@@H](O)CN1C(=O)OC(C)(C)C.CS(=O)(=O)Cl>>CNC(=O)[C@@H]1C[C@@H](OS(C)(=O)=O)CN1C(=O)OC(C)(C)C | [Cl-].[Na+].C(C)N(CC)CC.C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)O)C(NC)=O.CS(=O)(=O)Cl>>C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)OS(=O)(=O)C)C(NC)=O | [CH3:1][NH:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@@H:7]([OH:8])[CH2:13][N:14]1[C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21].Cl[S:9]([CH3:10])(=[O:11])=[O:12]>>[CH3:1][NH:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@@H:7]([O:8][S:9]([CH3:10])(=[O:11])=[O:12])[CH2:13][N:14]1[C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:2... | CNC(=O)[C@@H]1C[C@@H](O)CN1C(=O)OC(C)(C)C.CS(=O)(=O)Cl | CNC(=O)[C@@H]1C[C@@H](OS(C)(=O)=O)CN1C(=O)OC(C)(C)C | null | null | O1CCCC1 | Acylation | Formation of Sulfonic Esters | 641955d0081c80f158ce2aacd31873a3f3301c87ca0800cf263e288ba8390217 | 4f9373df8a11470603daf885a5777cebf95940370e32739263d35df0f171a0dd | C1CCNC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#7:5]-[C:6]-[C:7](-[OH;D1;+0:8])-[C:9]>>[#7:5]-[C:6]-[C:7](-[O;H0;D2;+0:8]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])-[C:9] | null | [] | null | null | 30 | MINUTE | 7.11 ml of triethylamine were added, whilst ice-cooling, to a solution of 11.29 g of (2S, 4R)-1-(t-butoxycarbonyl)-2-methylcarbamoyl-4-hydroxypyrrolidine [prepared as described in step (1) above] dissolved in 120 ml of dry tetrahydrofuran, and then 3.93 ml of methanesulfonyl chloride were added to the resulting mixture... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Sulfonyl halide | Mesylate | null | null | C1CC[NH]C1 | HCl | O1CCCC1 | null | 0.5 | CNC(=O)[C@@H]1C[C@@H](O)CN1C(=O)OC(C)(C)C.CS(=O)(=O)Cl>O1CCCC1>CNC(=O)[C@@H]1C[C@@H](OS(C)(=O)=O)CN1C(=O)OC(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0bd7b9bbd6fc49a99cff25ed87c706fd | CNC(=O)[C@@H]1C[C@@H](OS(C)(=O)=O)CN1C(=O)OC(C)(C)C.COc1ccc(CS)cc1>>CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C(=O)OC(C)(C)C | [Cl-].[Na+].[H-].[Na+].COC1=CC=C(CS)C=C1.C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)OS(=O)(=O)C)C(NC)=O>>C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(NC)=O | CS(=O)(=O)O[C@@H:7]1[CH2:6][C@@H:5]([C:3]([NH:2][CH3:1])=[O:4])[N:19]([C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[CH2:18]1.[SH:8][CH2:9][c:10]1[cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17]1>>[CH3:1][NH:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([S:8][CH2:9][c:10]2[cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16... | CNC(=O)[C@@H]1C[C@@H](OS(C)(=O)=O)CN1C(=O)OC(C)(C)C.COc1ccc(CS)cc1 | CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C(=O)OC(C)(C)C | null | null | CN(C=O)C.O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | ea9de8eedcb8c3411962b7e96bdbc0799f2ed8fdff8f60ac6688856d164fc003 | 5d51471fb107f265fe2b725316ea74298d6b5b18b8910d02b969c8ad6fbd6b39 | c1ccc(CS[C@H]2CCNC2)cc1 | C-S(=O)(=O)-O-[C@H;D3;+0:1]1-[C:2]-[#7:3](-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10])-[C:11](-[C:12](-[#7:13])=[O;D1;H0:14])-[C:15]-1.[SH;D1;+0:16]-[C:17]-[c:18]>>[#7:13]-[C:12](=[O;D1;H0:14])-[C:11]1-[C:15]-[C@H;D3;+0:1](-[S;H0;D2;+0:16]-[C:17]-[c:18])-[C:2]-[#7:3]-1-[C:4](=[O;D1;H0:5])... | null | [] | null | null | 30 | MINUTE | 1.80 g of sodium hydride (as a 55% w/w dispersion in mineral oil) was added, whilst ice-cooling, to a solution of 5.70 ml of 4-methoxybenzyl mercaptan dissolved in 100 ml of dry tetrahydrofuran, and the mixture was then stirred at 0° to 5° C. for 30 minutes. At the end of this time, a solution of 11.00 g of (2S, 4R)-1-... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aliphatic thiol | Monosulfide | C1CC[NH]C1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1 | MsOH.HO- | CN(C=O)C.O1CCCC1 | null | 0.5 | CNC(=O)[C@@H]1C[C@@H](OS(C)(=O)=O)CN1C(=O)OC(C)(C)C.COc1ccc(CS)cc1>CN(C=O)C.O1CCCC1>CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C(=O)OC(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0e70b857ff5341b6b9e0f7b265b239d3 | CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C(=O)OC(C)(C)C>>CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1 | C([O-])(O)=O.[Na+].O1CCOCC1.Cl.C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(NC)=O>>COC1=CC=C(CS[C@H]2C[C@H](NC2)C(NC)=O)C=C1 | CC(C)(C)OC(=O)[N:19]1[C@H:5]([C:3]([NH:2][CH3:1])=[O:4])[CH2:6][C@H:7]([S:8][CH2:9][c:10]2[cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17]2)[CH2:18]1>>[CH3:1][NH:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([S:8][CH2:9][c:10]2[cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17]2)[CH2:18][NH:19]1 | CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C(=O)OC(C)(C)C | CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1 | null | null | C(C)(=O)OCC | Reduction | Boc amine deprotection | 7b506000be0005f6be41b2386b5bd6a8c45f704baa22d692d2f2ec984758e4ad | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(CS[C@H]2CCNC2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1-[C:6](=[O;D1;H0:7])-[#7:8]-[C;D1;H3:9]>>[C;D1;H3:9]-[#7:8]-[C:6](=[O;D1;H0:7])-[C:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | 79.4 | [{"value": 79.4, "product": "COC1=CC=C(CS[C@H]2C[C@H](NC2)C(NC)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 52.5 ml of a 4N dioxane solution of hydrogen chloride were added, whilst ice-cooling, to a solution of 4.00 g of (2S, 4S)-1-(t-butoxycarbonyl)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine [prepared as described in step (3) above] dissolved in 50 ml of ethyl acetate. The mixture was stirred at 0° to 50° C. for 3... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]C1 | C1CCNC1 | C1CCNC1.c1ccccc1 | HO- | C(C)(=O)OCC | null | 0.5 | CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C(=O)OC(C)(C)C>C(C)(=O)OCC>CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b3ce27b511c44d5bba8fee0419416c71 | CI.CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1>>CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C | [Cl-].[Na+].CI.C([O-])(O)=O.[Na+].COC1=CC=C(CS[C@H]2C[C@H](NC2)C(NC)=O)C=C1>>COC1=CC=C(CS[C@H]2C[C@H](N(C2)C)C(NC)=O)C=C1 | I[CH3:20].[CH3:1][NH:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([S:8][CH2:9][c:10]2[cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17]2)[CH2:18][NH:19]1>>[CH3:1][NH:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([S:8][CH2:9][c:10]2[cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17]2)[CH2:18][N:19]1[CH3:20] | CI.CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1 | CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | f4b2dee8a5b3d3310bdcb922146a650e5f8d62398a9d05c3a8faedf2e64b9ccf | 7cc25fba33369069673bac5bd8fc404dc064da8d6c8cf4a77f21f4df0a617fe3 | c1ccc(CS[C@H]2CCNC2)cc1 | I-[CH3;D1;+0:1].[C;D1;H3:2]-[#7:3]-[C:4](=[O;D1;H0:5])-[C:6]1-[C:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[C;D1;H3:2]-[#7:3]-[C:4](=[O;D1;H0:5])-[C:6]1-[C:7]-[C:8]-[C:9]-[N;H0;D3;+0:10]-1-[CH3;D1;+0:1] | 21.1 | [{"value": 21.1, "product": "COC1=CC=C(CS[C@H]2C[C@H](N(C2)C)C(NC)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 244 μl of methyl iodide and 300 mg of sodium bicarbonate were added, whilst ice-cooling, to a solution of 1.00 g of (2S, 4S)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine [prepared as described in step (4) above] dissolved in 6 ml of dry dimethylformamide. The mixture was then stirred at 0° to 5° C. for 1 hour a... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1 | HI | CN(C=O)C | null | 1 | CI.CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1>CN(C=O)C>CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1d2785f1e38445e281416d2d2b06b4b3 | CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C.COS(=O)(=O)F>>CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)C[N+]1(C)C.O=S(=O)([O-])F | FS(=O)(=O)OC.COC1=CC=C(CS[C@H]2C[C@H](N(C2)C)C(NC)=O)C=C1>>S(=O)(=O)([O-])F.C[N+]1([C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(NC)=O)C | [CH3:1][NH:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([S:8][CH2:9][c:10]2[cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17]2)[CH2:18][N:19]1[CH3:20].[CH3:21][O:25][S:23](=[O:22])(=[O:24])[F:26]>>[CH3:1][NH:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([S:8][CH2:9][c:10]2[cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17]2)[CH2:18]... | CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C.COS(=O)(=O)F | CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)C[N+]1(C)C.O=S(=O)([O-])F | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 5f722cf633dcf9b31e6556ed21943419798499e4b62ddaf4985fd6638a78aed4 | 5a8d30abc7481f1c446ec3891ae2e6d38df9cf7a08165b843f1d24fc50c4b9cd | c1ccc(CS[C@H]2CC[NH2+]C2)cc1 | [C;D1;H3:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[C:5]1-[C:6]-[C:7]-[C:8]-[N;H0;D3;+0:9]-1-[C;D1;H3:10].[CH3;D1;+0:11]-[O;H0;D2;+0:12]-[#16:13](-[F;D1;H0:14])(=[O;D1;H0:15])=[O;D1;H0:16]>>[C;D1;H3:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[C:5]1-[C:6]-[C:7]-[C:8]-[N+;H0;D4:9]-1(-[C;D1;H3:10])-[CH3;D1;+0:11].[F;D1;H0:14]-[#16:13](-[O-;H0;D1:... | null | [] | null | null | 30 | MINUTE | 280 μl of methyl fluorosulfonate were added, whilst ice-cooling, to a solution of 210 mg of (2S, 4S)-4-(4-methoxybenzylthio)-1-methyl-2-methylcarbamoylpyrrolidine [prepared as described in step (5) above] dissolved in 30 ml of dry methylene chloride. The mixture was stirred at the same temperature for 30 minutes and th... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | C1CC[NH]C1 | C1CC[NH+]C1 | C1CC[NH+]C1.c1ccccc1 | null | C(Cl)Cl | null | 0.5 | CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C.COS(=O)(=O)F>C(Cl)Cl>CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)C[N+]1(C)C.O=S(=O)([O-])F |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ccf005369f574994b7154cc4045f7565 | CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(=O)O.CNC>>CN(C)C(=O)[C@@H]1C[C@@H](O)CN1C(=O)OC(C)(C)C | Cl.C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)O)C(=O)O.ClC(=O)OCC.CNC>>C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)O)C(N(C)C)=O | O[C:4](=[O:5])[C@@H:6]1[CH2:7][C@@H:8]([OH:9])[CH2:10][N:11]1[C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18].[CH3:1][NH:2][CH3:3]>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[C@@H:6]1[CH2:7][C@@H:8]([OH:9])[CH2:10][N:11]1[C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18] | CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(=O)O.CNC | CN(C)C(=O)[C@@H]1C[C@@H](O)CN1C(=O)OC(C)(C)C | null | null | O1CCCC1.C(C)N(CC)CC | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | C1CCNC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C:13].[C;D1;H3:14]-[NH;D2;+0:15]-[C;D1;H3:16]>>[C:13]-[#7:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:15... | null | [] | null | null | 2 | HOUR | 3.84 ml of triethylamine was added, at -15° to -20° C., to a solution of 5.8 g of (2S, 4R)-1-(t-butoxycarbonyl)-4-hydroxy-2-pyrrolidinecarboxylic acid dissolved in 85 ml of dry tetrahydrofuran, and then a solution of 2.63 ml of ethyl chloroformate in 25 ml of dry tetrahydrofuran was added to the resulting mixture at th... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | C1CC[NH]C1 | HO- | O1CCCC1.C(C)N(CC)CC | null | 2 | CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(=O)O.CNC>O1CCCC1.C(C)N(CC)CC>CN(C)C(=O)[C@@H]1C[C@@H](O)CN1C(=O)OC(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-daab5ee4b89e4b57bb5dd1d29f4fa7c5 | CN(C)C(=O)[C@@H]1C[C@@H](OS(C)(=O)=O)CN1C(=O)OC(C)(C)C.COc1ccc(CS)cc1>>COc1ccc(CS[C@H]2C[C@@H](C(=O)N(C)C)N(C(=O)OC(C)(C)C)C2)cc1 | [OH-].[Na+].COC1=CC=C(CS)C=C1.C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)OS(=O)(=O)C)C(N(C)C)=O>>C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(N(C)C)=O | CS(=O)(=O)O[C@@H:9]1[CH2:10][C@@H:11]([C:12](=[O:13])[N:14]([CH3:15])[CH3:16])[N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][SH:8])[cH:26][cH:27]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][C@H:9]2[CH2:10][C@@H:11]([C:12](=[O:13])[N:14]([CH3:1... | CN(C)C(=O)[C@@H]1C[C@@H](OS(C)(=O)=O)CN1C(=O)OC(C)(C)C.COc1ccc(CS)cc1 | COc1ccc(CS[C@H]2C[C@@H](C(=O)N(C)C)N(C(=O)OC(C)(C)C)C2)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | ea9de8eedcb8c3411962b7e96bdbc0799f2ed8fdff8f60ac6688856d164fc003 | 5d51471fb107f265fe2b725316ea74298d6b5b18b8910d02b969c8ad6fbd6b39 | c1ccc(CS[C@H]2CCNC2)cc1 | C-S(=O)(=O)-O-[C@@H;D3;+0:1]1-[C:2]-[C:3](-[C:4](-[#7:5])=[O;D1;H0:6])-[#7:7](-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C;D1;H3:14])-[C:15]-1.[SH;D1;+0:16]-[C:17]-[c:18]>>[#7:5]-[C:4](=[O;D1;H0:6])-[C:3]1-[C:2]-[C@H;D3;+0:1](-[S;H0;D2;+0:16]-[C:17]-[c:18])-[C:15]-[#7:7]-1-[C:8](=[O;D1;H0:9])-[#... | 31.3 | [{"value": 31.3, "product": "C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(N(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 151 mg of sodium hydroxide (as a 55% w/w dispersion in mineral oil) were added, whilst ice-cooling, to a solution of 532 mg of 4-methoxybenzyl mercaptan dissolved in 10 ml of dry dimethylformamide. The mixture was then stirred at room temperature for 30 minutes, after which 1.05 g of (2S, 4R)-1-(t-butoxycarbonyl)-2-(N,... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aliphatic thiol | Monosulfide | C1CC[NH]C1 | C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | MsOH.HO- | CN(C=O)C | null | 0.5 | CN(C)C(=O)[C@@H]1C[C@@H](OS(C)(=O)=O)CN1C(=O)OC(C)(C)C.COc1ccc(CS)cc1>CN(C=O)C>COc1ccc(CS[C@H]2C[C@@H](C(=O)N(C)C)N(C(=O)OC(C)(C)C)C2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e08bf8780bbe4cf28c4a3bcbffc10d69 | COc1ccc(CS[C@H]2C[C@@H](C(=O)N(C)C)N(C(=O)OC(C)(C)C)C2)cc1>>COc1ccc(CS[C@@H]2CN[C@H](C(=O)N(C)C)C2)cc1 | C([O-])(O)=O.[Na+].O1CCOCC1.Cl.C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(N(C)C)=O>>CN(C(=O)[C@H]1NC[C@H](C1)SCC1=CC=C(C=C1)OC)C | CC(C)(C)OC(=O)[N:11]1[CH2:10][C@@H:9]([S:8][CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:20][cH:19]2)[CH2:18][C@H:12]1[C:13](=[O:14])[N:15]([CH3:16])[CH3:17]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][C@@H:9]2[CH2:10][NH:11][C@H:12]([C:13](=[O:14])[N:15]([CH3:16])[CH3:17])[CH2:18]2)[cH:19][cH:20]1 | COc1ccc(CS[C@H]2C[C@@H](C(=O)N(C)C)N(C(=O)OC(C)(C)C)C2)cc1 | COc1ccc(CS[C@@H]2CN[C@H](C(=O)N(C)C)C2)cc1 | null | null | C(C)(=O)OCC | Reduction | Boc amine deprotection | 7b506000be0005f6be41b2386b5bd6a8c45f704baa22d692d2f2ec984758e4ad | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(CS[C@H]2CCNC2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1-[C:6](=[O;D1;H0:7])-[#7:8](-[C;D1;H3:9])-[C;D1;H3:10]>>[C;D1;H3:9]-[#7:8](-[C;D1;H3:10])-[C:6](=[O;D1;H0:7])-[C:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | 56.7 | [{"value": 56.7, "product": "CN(C(=O)[C@H]1NC[C@H](C1)SCC1=CC=C(C=C1)OC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | 1 ml of a 4N dioxane solution of hydrogen chloride was added, whilst ice-cooling, to a solution of 385 mg of (2S, 4S)-1-(t-butoxycarbonyl)-2-(N,N-dimethylcarbamoyl)-4-(4-methoxybenzylthio)pyrrolidine [prepared as described in step (3) above] dissolved in 1 ml of ethyl acetate, and the mixture was stirred at room temper... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]C1 | C1CCNC1 | c1ccccc1.C1CCNC1 | HO- | C(C)(=O)OCC | null | 1.5 | COc1ccc(CS[C@H]2C[C@@H](C(=O)N(C)C)N(C(=O)OC(C)(C)C)C2)cc1>C(C)(=O)OCC>COc1ccc(CS[C@@H]2CN[C@H](C(=O)N(C)C)C2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b9b5c0d6003640ca85d5ec6b4a599303 | CI.COc1ccc(CS[C@@H]2CN[C@H](C(=O)N(C)C)C2)cc1>>COc1ccc(CS[C@H]2C[C@@H](C(=O)N(C)C)N(C)C2)cc1 | C([O-])(O)=O.[Na+].C([O-])(O)=O.[Na+].CI.CN(C(=O)[C@H]1NC[C@H](C1)SCC1=CC=C(C=C1)OC)C>>CN(C(=O)[C@H]1N(C[C@H](C1)SCC1=CC=C(C=C1)OC)C)C | I[CH3:18].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][C@H:9]2[CH2:10][C@@H:11]([C:12](=[O:13])[N:14]([CH3:15])[CH3:16])[NH:17][CH2:19]2)[cH:20][cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][C@H:9]2[CH2:10][C@@H:11]([C:12](=[O:13])[N:14]([CH3:15])[CH3:16])[N:17]([CH3:18])[CH2:19]2)[cH:20][cH:21]1 | CI.COc1ccc(CS[C@@H]2CN[C@H](C(=O)N(C)C)C2)cc1 | COc1ccc(CS[C@H]2C[C@@H](C(=O)N(C)C)N(C)C2)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | f4b2dee8a5b3d3310bdcb922146a650e5f8d62398a9d05c3a8faedf2e64b9ccf | 7cc25fba33369069673bac5bd8fc404dc064da8d6c8cf4a77f21f4df0a617fe3 | c1ccc(CS[C@H]2CCNC2)cc1 | I-[CH3;D1;+0:1].[C;D1;H3:2]-[#7:3](-[C;D1;H3:4])-[C:5](=[O;D1;H0:6])-[C:7]1-[C:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[C;D1;H3:2]-[#7:3](-[C;D1;H3:4])-[C:5](=[O;D1;H0:6])-[C:7]1-[C:8]-[C:9]-[C:10]-[N;H0;D3;+0:11]-1-[CH3;D1;+0:1] | 26.4 | [{"value": 26.4, "product": "CN(C(=O)[C@H]1N(C[C@H](C1)SCC1=CC=C(C=C1)OC)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 84 mg of sodium bicarbonate and 41 μl of methyl iodide were added, whilst ice-cooling, to a solution of 163 mg of (2S, 4S)-2-(N,N-dimethylcarbamoyl)-4-(4-methoxybenzylthio)pyrrolidine [prepared as described in step (4) above] dissolved in 1.5 ml of dry dimethylformamide, and the mixture was stirred at room temperature ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HI | CN(C=O)C | null | 4 | CI.COc1ccc(CS[C@@H]2CN[C@H](C(=O)N(C)C)C2)cc1>CN(C=O)C>COc1ccc(CS[C@H]2C[C@@H](C(=O)N(C)C)N(C)C2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-372a5e01fff64e0fb51a06075258f893 | COC(=O)[C@@H]1CC(O)CN1C(=O)OC(C)(C)C.CS(=O)(=O)Cl>>COC(=O)[C@@H]1C[C@@H](OS(C)(=O)=O)CN1C(=O)OC(C)(C)C | [Cl-].[Na+].CS(=O)(=O)Cl.C(C)N(CC)CC.C(C)(C)(C)OC(=O)N1[C@H](C(=O)OC)CC(C1)O>>C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)OS(=O)(=O)C)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][CH:7]([OH:8])[CH2:13][N:14]1[C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21].Cl[S:9]([CH3:10])(=[O:11])=[O:12]>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@@H:7]([O:8][S:9]([CH3:10])(=[O:11])=[O:12])[CH2:13][N:14]1[C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21] | COC(=O)[C@@H]1CC(O)CN1C(=O)OC(C)(C)C.CS(=O)(=O)Cl | COC(=O)[C@@H]1C[C@@H](OS(C)(=O)=O)CN1C(=O)OC(C)(C)C | null | null | O1CCCC1 | Acylation | Formation of Sulfonic Esters | 641955d0081c80f158ce2aacd31873a3f3301c87ca0800cf263e288ba8390217 | 4f9373df8a11470603daf885a5777cebf95940370e32739263d35df0f171a0dd | C1CCNC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]1-[C:9]-[CH;D3;+0:10](-[OH;D1;+0:11])-[C:12]-[#7:13]-1-[C:14](=[O;D1;H0:15])-[#8:16]-[C:17](-[C;D1;H3:18])(-[C;D1;H3:19])-[C;D1;H3:20]>>[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]1-[C:9]-[C@@H;D3;+0:10](-[O;H0;D2;+0:11]-[S;H0;D4;+0:1](-[C;D1... | null | [] | null | null | 1 | HOUR | 2.02 ml of methanesulfonyl chloride, followed by 3.65 ml of triethylamine were added, whilst ice-cooling, to a solution of 6.1 g of methyl 1-(t-butoxycarbonyl)-4-hydroxyprolinate [prepared as described in step (6) above] dissolved in 120 ml of dry tetrahydrofuran. The mixture was stirred first at 0° to 5° C. for 1 hour... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Sulfonyl halide | Mesylate | null | null | C1CC[NH]C1 | HCl | O1CCCC1 | null | 1 | COC(=O)[C@@H]1CC(O)CN1C(=O)OC(C)(C)C.CS(=O)(=O)Cl>O1CCCC1>COC(=O)[C@@H]1C[C@@H](OS(C)(=O)=O)CN1C(=O)OC(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2c2ec0e62c9945a7ac22809a68962be3 | COC(=O)[C@@H]1C[C@@H](OS(C)(=O)=O)CN1C(=O)OC(C)(C)C.COc1ccc(CS)cc1>>COC(=O)C1CC(SCc2ccc(OC)cc2)CN1C(=O)OC(C)(C)C | [Cl-].[Na+].[H-].[Na+].COC1=CC=C(CS)C=C1.C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)OS(=O)(=O)C)C(=O)OC>>C(C)(C)(C)OC(=O)N1C(CC(C1)SCC1=CC=C(C=C1)OC)C(=O)OC | CS(=O)(=O)O[C@@H:7]1[CH2:6][C@@H:5]([C:3]([O:2][CH3:1])=[O:4])[N:19]([C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[CH2:18]1.[SH:8][CH2:9][c:10]1[cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH:7]([S:8][CH2:9][c:10]2[cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16][cH:... | COC(=O)[C@@H]1C[C@@H](OS(C)(=O)=O)CN1C(=O)OC(C)(C)C.COc1ccc(CS)cc1 | COC(=O)C1CC(SCc2ccc(OC)cc2)CN1C(=O)OC(C)(C)C | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | ea9de8eedcb8c3411962b7e96bdbc0799f2ed8fdff8f60ac6688856d164fc003 | 5d51471fb107f265fe2b725316ea74298d6b5b18b8910d02b969c8ad6fbd6b39 | c1ccc(CSC2CCNC2)cc1 | C-S(=O)(=O)-O-[C@H;D3;+0:1]1-[C:2]-[#7:3](-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10])-[C:11](-[C:12](-[#8:13])=[O;D1;H0:14])-[C:15]-1.[SH;D1;+0:16]-[C:17]-[c:18]>>[#8:13]-[C:12](=[O;D1;H0:14])-[C:11]1-[C:15]-[CH;D3;+0:1](-[S;H0;D2;+0:16]-[C:17]-[c:18])-[C:2]-[#7:3]-1-[C:4](=[O;D1;H0:5])-... | null | [] | null | null | 30 | MINUTE | 1.11 g of sodium hydride (as a 55% w/w dispersion in mineral oil) was added, whilst ice-cooling, to a solution of 3.51 ml of 4-methoxybenzyl mercaptan dissolved in 60 ml of dry dimethylformamide, and the mixture was stirred at room temperature for 30 minutes. At the end of this time, a solution of 8.13 g of (2S, 4R)-1-... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aliphatic thiol | Monosulfide | C1CC[NH]C1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1 | MsOH.HO- | CN(C=O)C | null | 0.5 | COC(=O)[C@@H]1C[C@@H](OS(C)(=O)=O)CN1C(=O)OC(C)(C)C.COc1ccc(CS)cc1>CN(C=O)C>COC(=O)C1CC(SCc2ccc(OC)cc2)CN1C(=O)OC(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6acb4cb55a2a48bf83975baefbb5272b | COC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C(=O)OC(C)(C)C>>COC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1 | Cl.C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(=O)OC.C([O-])(O)=O.[Na+]>>COC1=CC=C(CS[C@H]2C[C@H](NC2)C(=O)OC)C=C1 | CC(C)(C)OC(=O)[N:19]1[C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][C@H:7]([S:8][CH2:9][c:10]2[cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17]2)[CH2:18]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([S:8][CH2:9][c:10]2[cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17]2)[CH2:18][NH:19]1 | COC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C(=O)OC(C)(C)C | COC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1 | null | null | C(C)(=O)OCC | Reduction | Boc amine deprotection | 7b506000be0005f6be41b2386b5bd6a8c45f704baa22d692d2f2ec984758e4ad | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(CS[C@H]2CCNC2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1-[C:6](=[O;D1;H0:7])-[#8:8]-[C;D1;H3:9]>>[C;D1;H3:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[C:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | 85.7 | [{"value": 85.7, "product": "COC1=CC=C(CS[C@H]2C[C@H](NC2)C(=O)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 27.3 ml of a 4N ethyl acetate solution of hydrogen chloride were added, whilst ice-cooling, to a solution of 5.22 g of (2S, 4S)-1-(t-butoxycarbonyl)-4-(4-methoxybenzylthio)-2-methoxycarbonylpyrrolidine [prepared as described in step (8) above] dissolved in 14 ml of ethyl acetate, and the mixture was stirred at room tem... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]C1 | C1CCNC1 | C1CCNC1.c1ccccc1 | HO- | C(C)(=O)OCC | null | 1 | COC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C(=O)OC(C)(C)C>C(C)(=O)OCC>COC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2d65ae8fa14242fd82d46e52981a6b6d | CI.COC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1>>COC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C | C([O-])(O)=O.[Na+].C([O-])(O)=O.[Na+].CI.COC1=CC=C(CS[C@H]2C[C@H](NC2)C(=O)OC)C=C1>>COC1=CC=C(CS[C@H]2C[C@H](N(C2)C)C(=O)OC)C=C1 | I[CH3:20].[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([S:8][CH2:9][c:10]2[cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17]2)[CH2:18][NH:19]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([S:8][CH2:9][c:10]2[cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17]2)[CH2:18][N:19]1[CH3:20] | CI.COC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1 | COC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | f4b2dee8a5b3d3310bdcb922146a650e5f8d62398a9d05c3a8faedf2e64b9ccf | 7cc25fba33369069673bac5bd8fc404dc064da8d6c8cf4a77f21f4df0a617fe3 | c1ccc(CS[C@H]2CCNC2)cc1 | I-[CH3;D1;+0:1].[C;D1;H3:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[C:6]1-[C:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[C;D1;H3:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[C:6]1-[C:7]-[C:8]-[C:9]-[N;H0;D3;+0:10]-1-[CH3;D1;+0:1] | 27.9 | [{"value": 27.9, "product": "COC1=CC=C(CS[C@H]2C[C@H](N(C2)C)C(=O)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | 1.18 g of sodium bicarbonate and 0.876 ml of methyl iodide were added, whilst ice-cooling, to a solution of 3.3 g of (2S, 4S)-4-(4-methoxybenzylthio)-2-methoxycarbonylpyrrolidine [prepared as described in step (9) above] dissolved in 30 ml of dry dimethylformamide, and the mixture was stirred at room temperature for 5 ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1 | HI | CN(C=O)C | null | 5 | CI.COC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1>CN(C=O)C>COC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f4f554a837c44d9589165fa8b7cfb9eb | COC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C>>COc1ccc(CS[C@H]2C[C@@H](C(=O)O)N(C)C2)cc1 | Cl.[OH-].[Na+].COC1=CC=C(CS[C@H]2C[C@H](N(C2)C)C(=O)OC)C=C1>>C(=O)(O)[C@H]1N(C[C@H](C1)SCC1=CC=C(C=C1)OC)C | C[O:14][C:12]([C@@H:11]1[CH2:10][C@H:9]([S:8][CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:19][cH:18]2)[CH2:17][N:15]1[CH3:16])=[O:13]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][C@H:9]2[CH2:10][C@@H:11]([C:12](=[O:13])[OH:14])[N:15]([CH3:16])[CH2:17]2)[cH:18][cH:19]1 | COC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C | COc1ccc(CS[C@H]2C[C@@H](C(=O)O)N(C)C2)cc1 | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(CS[C@H]2CCNC2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7:5]>>[#7:5]-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | 3 | HOUR | 1.92 ml of a 1N aqueous solution of sodium hydroxide was added to a solution of 378 mg of (2S, 4S)-4-(4-methoxybenzylthio)-2-methoxycarbonyl-1-methylpyrrolidine [prepared as described in step (10) above] dissolved in 3.84 ml of methanol, and the mixture was stirred at room temperature for 3 hours, At the end of this ti... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.C1CC[NH]C1 | Other | CO | null | 3 | COC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C>CO>COc1ccc(CS[C@H]2C[C@@H](C(=O)O)N(C)C2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-57c4dcadfa504bd3b6a8c19ef17eb2ac | COS(=O)(=O)F.COc1ccc(CS[C@H]2C[C@@H](C(=O)N(C)C)N(C)C2)cc1>>COc1ccc(CS[C@H]2C[C@@H](C(=O)N(C)C)[N+](C)(C)C2)cc1.O=S(=O)([O-])F | FS(=O)(=O)OC.CN(C(=O)[C@H]1N(C[C@H](C1)SCC1=CC=C(C=C1)OC)C)C>>FS(=O)(=O)[O-].CN(C(=O)[C@H]1[N+](C[C@H](C1)SCC1=CC=C(C=C1)OC)(C)C)C | [CH3:19][O:26][S:24](=[O:23])(=[O:25])[F:27].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][C@H:9]2[CH2:10][C@@H:11]([C:12](=[O:13])[N:14]([CH3:15])[CH3:16])[N:17]([CH3:18])[CH2:20]2)[cH:21][cH:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][C@H:9]2[CH2:10][C@@H:11]([C:12](=[O:13])[N:14]([CH3:15])[CH3:16])[N+:... | COS(=O)(=O)F.COc1ccc(CS[C@H]2C[C@@H](C(=O)N(C)C)N(C)C2)cc1 | COc1ccc(CS[C@H]2C[C@@H](C(=O)N(C)C)[N+](C)(C)C2)cc1.O=S(=O)([O-])F | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 5f722cf633dcf9b31e6556ed21943419798499e4b62ddaf4985fd6638a78aed4 | 5a8d30abc7481f1c446ec3891ae2e6d38df9cf7a08165b843f1d24fc50c4b9cd | c1ccc(CS[C@H]2CC[NH2+]C2)cc1 | [C;D1;H3:1]-[#7:2](-[C;D1;H3:3])-[C:4](=[O;D1;H0:5])-[C:6]1-[C:7]-[C:8]-[C:9]-[N;H0;D3;+0:10]-1-[C;D1;H3:11].[CH3;D1;+0:12]-[O;H0;D2;+0:13]-[#16:14](-[F;D1;H0:15])(=[O;D1;H0:16])=[O;D1;H0:17]>>[C;D1;H3:1]-[#7:2](-[C;D1;H3:3])-[C:4](=[O;D1;H0:5])-[C:6]1-[C:7]-[C:8]-[C:9]-[N+;H0;D4:10]-1(-[C;D1;H3:11])-[CH3;D1;+0:12].[F;... | null | [] | null | null | 2 | HOUR | 139 μl of methyl fluorosulfonate were added, whilst ice-cooling, to a solution of 190 mg of (2S, 4S)-2-(N,N-dimethylcarbamoyl)-4-(4-methoxybenzylthio)-1-methylpyrrolidine [prepared as described in step (5) or (11) above] dissolved in 3.8 ml of methylene chloride, and the mixture was stirred at room temperature for 2 ho... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | C1CC[NH]C1 | C1CC[NH+]C1 | c1ccccc1.C1CC[NH+]C1 | null | C(Cl)Cl | null | 2 | COS(=O)(=O)F.COc1ccc(CS[C@H]2C[C@@H](C(=O)N(C)C)N(C)C2)cc1>C(Cl)Cl>COc1ccc(CS[C@H]2C[C@@H](C(=O)N(C)C)[N+](C)(C)C2)cc1.O=S(=O)([O-])F |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e65f24035a9c4030ba5dd6e5e6051a44 | CC(C)(C)OC(=O)N1CC[C@@H](O)C1.CS(=O)(=O)Cl>>CC(C)(C)OC(=O)N1CC[C@@H](OS(C)(=O)=O)C1 | [Cl-].[Na+].C(C)N(CC)CC.CS(=O)(=O)Cl.C(C)(C)(C)OC(=O)N1C[C@@H](CC1)O>>C(C)(C)(C)OC(=O)N1C[C@@H](CC1)OS(=O)(=O)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@@H:11]([OH:12])[CH2:17]1.Cl[S:13]([CH3:14])(=[O:15])=[O:16]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@@H:11]([O:12][S:13]([CH3:14])(=[O:15])=[O:16])[CH2:17]1 | CC(C)(C)OC(=O)N1CC[C@@H](O)C1.CS(=O)(=O)Cl | CC(C)(C)OC(=O)N1CC[C@@H](OS(C)(=O)=O)C1 | null | null | O1CCCC1 | Acylation | Formation of Sulfonic Esters | 641955d0081c80f158ce2aacd31873a3f3301c87ca0800cf263e288ba8390217 | 4f9373df8a11470603daf885a5777cebf95940370e32739263d35df0f171a0dd | C1CCNC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#7:5]-[C:6]-[C:7](-[OH;D1;+0:8])-[C:9]>>[#7:5]-[C:6]-[C:7](-[O;H0;D2;+0:8]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])-[C:9] | null | [] | null | null | 30 | MINUTE | 16.91 ml of triethylamine and 9.36 ml of methanesulfonyl chloride were added, in that order, whilst ice-cooling, to a solution of 25 g of (3R)-1-t-butoxycarbonyl-3-hydroxypyrrolidine dissolved in 250 ml of dry tetrahydrofuran, and the mixture was stirred at 0° to 5° C. for 30 minutes and then at 15° C. for 30 minutes. ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Sulfonyl halide | Mesylate | null | null | C1CC[NH]C1 | HCl | O1CCCC1 | null | 0.5 | CC(C)(C)OC(=O)N1CC[C@@H](O)C1.CS(=O)(=O)Cl>O1CCCC1>CC(C)(C)OC(=O)N1CC[C@@H](OS(C)(=O)=O)C1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3b009115c3e44b76ae4e4b1e1d6eee13 | CC(C)(C)OC(=O)N1CC[C@@H](OS(C)(=O)=O)C1.COc1ccc(CS)cc1>>COc1ccc(CS[C@H]2CCN(C(=O)OC(C)(C)C)C2)cc1 | [Cl-].[Na+].[H-].[Na+].COC1=CC=C(CS)C=C1.C(C)(C)(C)OC(=O)N1C[C@@H](CC1)OS(=O)(=O)C>>C(C)(C)(C)OC(=O)N1C[C@H](CC1)SCC1=CC=C(C=C1)OC | CS(=O)(=O)O[C@@H:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][SH:8])[cH:21][cH:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][C@H:9]2[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20]2... | CC(C)(C)OC(=O)N1CC[C@@H](OS(C)(=O)=O)C1.COc1ccc(CS)cc1 | COc1ccc(CS[C@H]2CCN(C(=O)OC(C)(C)C)C2)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | ea9de8eedcb8c3411962b7e96bdbc0799f2ed8fdff8f60ac6688856d164fc003 | 5d51471fb107f265fe2b725316ea74298d6b5b18b8910d02b969c8ad6fbd6b39 | c1ccc(CS[C@H]2CCNC2)cc1 | C-S(=O)(=O)-O-[C@@H;D3;+0:1]1-[C:2]-[C:3]-[#7:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11])-[C:12]-1.[SH;D1;+0:13]-[C:14]-[c:15]>>[C;D1;H3:9]-[C:8](-[C;D1;H3:10])(-[C;D1;H3:11])-[#8:7]-[C:5](=[O;D1;H0:6])-[#7:4]1-[C:3]-[C:2]-[C@H;D3;+0:1](-[S;H0;D2;+0:13]-[C:14]-[c:15])-[C:12]-1 | null | [] | null | null | 30 | MINUTE | 5.32 g of sodium hydride (as a 55% w/w dispersion in mineral oil) were added, whilst ice-cooling, to a solution of 16.86 ml of 4-methoxybenzyl mercaptan dissolved in 200 ml of dry dimethylformamide, and the mixture was then stirred at room temperature for 30 minutes. At the end of this time, a solution of 31.00 g of (3... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aliphatic thiol | Monosulfide | C1CC[NH]C1 | C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | MsOH.HO- | CN(C=O)C | null | 0.5 | CC(C)(C)OC(=O)N1CC[C@@H](OS(C)(=O)=O)C1.COc1ccc(CS)cc1>CN(C=O)C>COc1ccc(CS[C@H]2CCN(C(=O)OC(C)(C)C)C2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-757ef081a3af49d2a9a2d7813d18eacf | COc1ccc(CS[C@@H]2CCN(C(=O)OC(C)(C)C)C2)cc1>>COc1ccc(CS[C@H]2CCNC2)cc1 | Cl.C(C)(C)(C)OC(=O)N1C[C@@H](CC1)SCC1=CC=C(C=C1)OC>>Cl.COC1=CC=C(CS[C@@H]2CNCC2)C=C1 | CC(C)(C)OC(=O)[N:12]1[CH2:11][CH2:10][C@@H:9]([S:8][CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:15][cH:14]2)[CH2:13]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][C@H:9]2[CH2:10][CH2:11][NH:12][CH2:13]2)[cH:14][cH:15]1 | COc1ccc(CS[C@@H]2CCN(C(=O)OC(C)(C)C)C2)cc1 | COc1ccc(CS[C@H]2CCNC2)cc1 | null | null | C(C)(=O)OCC.C(C)(C)OC(C)C | Reduction | Boc amine deprotection | 7b506000be0005f6be41b2386b5bd6a8c45f704baa22d692d2f2ec984758e4ad | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(CS[C@H]2CCNC2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1>>[C:3]1-[C:2]-[NH;D2;+0:1]-[C:5]-[C:4]-1 | null | [] | null | null | 30 | MINUTE | 106 ml of a 4N ethyl acetate solution of hydrogen chloride were added, whilst ice-cooling, to a solution of 27.50 g of (3R)-1-t-butoxycarbonyl-3-(4-methoxybenzylthio)pyrrolidine [prepared as described in step (2) above] dissolved in 100 ml of ethyl acetate, and the mixture was stirred at 0° to 5° C. for 30 minutes and ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]C1 | C1CCNC1 | c1ccccc1.C1CCNC1 | HO- | C(C)(=O)OCC.C(C)(C)OC(C)C | null | 0.5 | COc1ccc(CS[C@@H]2CCN(C(=O)OC(C)(C)C)C2)cc1>C(C)(=O)OCC.C(C)(C)OC(C)C>COc1ccc(CS[C@H]2CCNC2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3f825583ac204effbee8944eb1dc37d3 | COS(=O)(=O)F.COc1ccc(CS[C@H]2CCN(C)C2)cc1>>COc1ccc(CS[C@H]2CC[N+](C)(C)C2)cc1.O=S(=O)([O-])F | FS(=O)(=O)OC.COC1=CC=C(CS[C@@H]2CN(CC2)C)C=C1>>FS(=O)(=O)[O-].C[N+]1(C[C@H](CC1)SCC1=CC=C(C=C1)OC)C | [CH3:13][O:21][S:19](=[O:18])(=[O:20])[F:22].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][C@H:9]2[CH2:10][CH2:11][N:12]([CH3:14])[CH2:15]2)[cH:16][cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][C@H:9]2[CH2:10][CH2:11][N+:12]([CH3:13])([CH3:14])[CH2:15]2)[cH:16][cH:17]1.[O:18]=[S:19](=[O:20])([O-:21])[F:2... | COS(=O)(=O)F.COc1ccc(CS[C@H]2CCN(C)C2)cc1 | COc1ccc(CS[C@H]2CC[N+](C)(C)C2)cc1.O=S(=O)([O-])F | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 5f722cf633dcf9b31e6556ed21943419798499e4b62ddaf4985fd6638a78aed4 | 5a8d30abc7481f1c446ec3891ae2e6d38df9cf7a08165b843f1d24fc50c4b9cd | c1ccc(CS[C@H]2CC[NH2+]C2)cc1 | [C;D1;H3:1]-[N;H0;D3;+0:2]1-[C:3]-[C:4]-[C:5]-[C:6]-1.[CH3;D1;+0:7]-[O;H0;D2;+0:8]-[#16:9](-[F;D1;H0:10])(=[O;D1;H0:11])=[O;D1;H0:12]>>[C;D1;H3:1]-[N+;H0;D4:2]1(-[CH3;D1;+0:7])-[C:3]-[C:4]-[C:5]-[C:6]-1.[F;D1;H0:10]-[#16:9](-[O-;H0;D1:8])(=[O;D1;H0:11])=[O;D1;H0:12] | null | [] | null | null | 30 | MINUTE | 118 μl of methyl fluorosulfonate were added, whilst ice-cooling, to a solution of 340 mg of (3S)-3-(4-methoxybenzylthio)-1-methylpyrrolidine [prepared as described in step (4) above] dissolved in 20 ml of dry methylene chloride. The mixture was then stirred at the same temperature for 30 minutes and then at room temper... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | C1CC[NH]C1 | C1CC[NH+]C1 | c1ccccc1.C1CC[NH+]C1 | null | C(Cl)Cl | null | 0.5 | COS(=O)(=O)F.COc1ccc(CS[C@H]2CCN(C)C2)cc1>C(Cl)Cl>COc1ccc(CS[C@H]2CC[N+](C)(C)C2)cc1.O=S(=O)([O-])F |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c4d16722518f4ca28ee5c209fc5afdcf | CN1CCC(O)CC1.CS(=O)(=O)Cl>>CN1CCC(OS(C)(=O)=O)CC1 | [Cl-].[Na+].C(C)N(CC)CC.CS(=O)(=O)Cl.OC1CCN(CC1)C>>CS(=O)(=O)OC1CCN(CC1)C | [CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([OH:6])[CH2:11][CH2:12]1.Cl[S:7]([CH3:8])(=[O:9])=[O:10]>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([O:6][S:7]([CH3:8])(=[O:9])=[O:10])[CH2:11][CH2:12]1 | CN1CCC(O)CC1.CS(=O)(=O)Cl | CN1CCC(OS(C)(=O)=O)CC1 | null | null | O1CCCC1 | Acylation | Formation of Sulfonic Esters | 641955d0081c80f158ce2aacd31873a3f3301c87ca0800cf263e288ba8390217 | 4f9373df8a11470603daf885a5777cebf95940370e32739263d35df0f171a0dd | C1CCNCC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6](-[OH;D1;+0:7])-[C:8]>>[C:5]-[C:6](-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])-[C:8] | null | [] | null | null | 2 | HOUR | 13.3 ml of triethylamine and subsequently 7.4 ml of methanesulfonyl chloride were added, whilst ice-cooling, to a solution of 10 g of 4-hydroxy-1-methylpiperidine dissolved in 100 ml of dry tetrahydrofuran. The mixture was then stirred at 0° to 5° C. for 2 hours and then at room temperature for 1.5 hours, after which i... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Sulfonyl halide | Mesylate | null | null | C1CC[NH]CC1 | HCl | O1CCCC1 | null | 2 | CN1CCC(O)CC1.CS(=O)(=O)Cl>O1CCCC1>CN1CCC(OS(C)(=O)=O)CC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f4333880ec444bb9b8b94a7c224f7aa8 | CN1CCC(OS(C)(=O)=O)CC1.COc1ccc(CS)cc1>>COc1ccc(CSC2CCN(C)CC2)cc1 | [Cl-].[Na+].[H-].[Na+].COC1=CC=C(CS)C=C1.CS(=O)(=O)OC1CCN(CC1)C>>COC1=CC=C(CSC2CCN(CC2)C)C=C1 | CS(=O)(=O)O[CH:9]1[CH2:10][CH2:11][N:12]([CH3:13])[CH2:14][CH2:15]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][SH:8])[cH:16][cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][CH:9]2[CH2:10][CH2:11][N:12]([CH3:13])[CH2:14][CH2:15]2)[cH:16][cH:17]1 | CN1CCC(OS(C)(=O)=O)CC1.COc1ccc(CS)cc1 | COc1ccc(CSC2CCN(C)CC2)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 313505334603d5eac09254d8b199aa4b8e648a3f37749e885705f1cc63a09927 | 5d51471fb107f265fe2b725316ea74298d6b5b18b8910d02b969c8ad6fbd6b39 | c1ccc(CSC2CCNCC2)cc1 | C-S(=O)(=O)-O-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[SH;D1;+0:7]-[C:8]-[c:9]>>[c:9]-[C:8]-[S;H0;D2;+0:7]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1 | null | [] | null | null | 30 | MINUTE | 10.9 ml of 4-methoxybenzyl mercaptan were dissolved in 55 ml of dry dimethylformamide, and 3.4 g of sodium hydride (as a 55% w/w suspension in mineral oil) were added to the solution, whilst ice-cooling. The mixture was then stirred at room temperature for 30 minutes. At the end of this time, a solution of 12.6 g of 4-... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aliphatic thiol | Monosulfide | C1CC[NH]CC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | MsOH.HO- | CN(C=O)C | null | 0.5 | CN1CCC(OS(C)(=O)=O)CC1.COc1ccc(CS)cc1>CN(C=O)C>COc1ccc(CSC2CCN(C)CC2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-cf85995aab2247649fbb7de51c4ee7a6 | CCN1C[C@@H](SCc2ccc(OC)cc2)C[C@H]1C(=O)N(C)C.COS(=O)(=O)F>>CC[N+]1(C)C[C@@H](SCc2ccc(OC)cc2)C[C@H]1C(=O)N(C)C.O=S(=O)([O-])F | FS(=O)(=O)OC.CN(C(=O)[C@H]1N(C[C@H](C1)SCC1=CC=C(C=C1)OC)CC)C>>FS(=O)(=O)[O-].CN(C(=O)[C@H]1[N+](C[C@H](C1)SCC1=CC=C(C=C1)OC)(C)CC)C | [CH3:1][CH2:2][N:3]1[CH2:5][C@@H:6]([S:7][CH2:8][c:9]2[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16]2)[CH2:17][C@H:18]1[C:19](=[O:20])[N:21]([CH3:22])[CH3:23].[CH3:4][O:27][S:25](=[O:24])(=[O:26])[F:28]>>[CH3:1][CH2:2][N+:3]1([CH3:4])[CH2:5][C@@H:6]([S:7][CH2:8][c:9]2[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][cH:1... | CCN1C[C@@H](SCc2ccc(OC)cc2)C[C@H]1C(=O)N(C)C.COS(=O)(=O)F | CC[N+]1(C)C[C@@H](SCc2ccc(OC)cc2)C[C@H]1C(=O)N(C)C.O=S(=O)([O-])F | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 5f722cf633dcf9b31e6556ed21943419798499e4b62ddaf4985fd6638a78aed4 | 5a8d30abc7481f1c446ec3891ae2e6d38df9cf7a08165b843f1d24fc50c4b9cd | c1ccc(CS[C@H]2CC[NH2+]C2)cc1 | [C;D1;H3:1]-[C:2]-[N;H0;D3;+0:3]1-[C:4]-[C:5]-[C:6]-[C:7]-1-[C:8](=[O;D1;H0:9])-[#7:10](-[C;D1;H3:11])-[C;D1;H3:12].[CH3;D1;+0:13]-[O;H0;D2;+0:14]-[#16:15](-[F;D1;H0:16])(=[O;D1;H0:17])=[O;D1;H0:18]>>[C;D1;H3:1]-[C:2]-[N+;H0;D4:3]1(-[CH3;D1;+0:13])-[C:4]-[C:5]-[C:6]-[C:7]-1-[C:8](=[O;D1;H0:9])-[#7:10](-[C;D1;H3:11])-[C... | null | [] | null | null | 2 | HOUR | 128 μl of methyl fluorosulfonate were added to a solution of 438 mg of (2S, 4S)-2-(N,N-dimethylcarbamoyl)-1-ethyl-4-(4-methoxybenzylthio)pyrrolidine dissolved in 10 ml of methylene chloride, and the mixture was stirred at room temperature for 2 hours. At the end of this time, the solvent was removed by distillation und... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | C1CC[NH]C1 | C1CC[NH+]C1 | C1CC[NH+]C1.c1ccccc1 | null | C(Cl)Cl | null | 2 | CCN1C[C@@H](SCc2ccc(OC)cc2)C[C@H]1C(=O)N(C)C.COS(=O)(=O)F>C(Cl)Cl>CC[N+]1(C)C[C@@H](SCc2ccc(OC)cc2)C[C@H]1C(=O)N(C)C.O=S(=O)([O-])F |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b28c3c4412f2482a9c5bfbab0040da2c | C=O.COC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1>>COC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C | [OH-].[Na+].[Cl-].[Na+].C=O.COC1=CC=C(CS[C@H]2C[C@H](NC2)C(=O)OC)C=C1.C(#N)[BH3-].[Na+]>>COC1=CC=C(CS[C@H]2C[C@H](N(C2)C)C(=O)OC)C=C1 | O=[CH2:20].[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([S:8][CH2:9][c:10]2[cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17]2)[CH2:18][NH:19]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([S:8][CH2:9][c:10]2[cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17]2)[CH2:18][N:19]1[CH3:20] | C=O.COC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1 | COC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C | null | null | C(C)#N.C(C)(=O)O | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Secondary Amine Methylation | 91bb2ea8aeb046c2c7c6bbf5485a7fce0a359aeb3adea3549d5b06757bc9a669 | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | c1ccc(CS[C@H]2CCNC2)cc1 | O=[CH2;D1;+0:1].[C;D1;H3:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[C:6]1-[C:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[C;D1;H3:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[C:6]1-[C:7]-[C:8]-[C:9]-[N;H0;D3;+0:10]-1-[CH3;D1;+0:1] | 55.5 | [{"value": 55.5, "product": "COC1=CC=C(CS[C@H]2C[C@H](N(C2)C)C(=O)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 3.43 ml of 35% formalin were added to a solution of 2.25 g of (2S, 4S)-4-(4-methoxybenzylthio)-2-methoxycarbonylpyrrolidine dissolved in 42 ml of acetonitrile. Subsequently, 804 mg of sodium cyanoborohydride were divided into three portions and added to the mixture over a period of 5 minutes. The mixture was then stirr... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1 | Other | C(C)#N.C(C)(=O)O | null | 0.5 | C=O.COC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1>C(C)#N.C(C)(=O)O>COC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5166f33815724bebbf71b60cc76c448c | COC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C>>COc1ccc(CS[C@H]2C[C@@H](C(=O)O)N(C)C2)cc1 | Cl.[OH-].[Na+].COC1=CC=C(CS[C@H]2C[C@H](N(C2)C)C(=O)OC)C=C1>>C(=O)(O)[C@H]1N(C[C@H](C1)SCC1=CC=C(C=C1)OC)C | C[O:14][C:12]([C@@H:11]1[CH2:10][C@H:9]([S:8][CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:19][cH:18]2)[CH2:17][N:15]1[CH3:16])=[O:13]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][C@H:9]2[CH2:10][C@@H:11]([C:12](=[O:13])[OH:14])[N:15]([CH3:16])[CH2:17]2)[cH:18][cH:19]1 | COC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C | COc1ccc(CS[C@H]2C[C@@H](C(=O)O)N(C)C2)cc1 | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(CS[C@H]2CCNC2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7:5]>>[#7:5]-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 120.2 | [{"value": 120.2, "product": "C(=O)(O)[C@H]1N(C[C@H](C1)SCC1=CC=C(C=C1)OC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 5.32 ml of a 1N aqueous solution of sodium hydroxide were added to a solution of 1.31 g of (2S, 4S)-4-(4-methoxybenzylthio)-2-methoxycarbonyl-1-methylpyrrolidine dissolved in 11 ml of methanol, and the mixture was stirred at room temperature for 2 hours. At the end of this time, it was neutralized with 5.32 ml of 1N aq... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.C1CC[NH]C1 | Other | CO | null | 2 | COC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C>CO>COc1ccc(CS[C@H]2C[C@@H](C(=O)O)N(C)C2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ad59de36260c4266b878a79c69cfa272 | CCI.COc1ccc(CS[C@@H]2CN[C@H](C(N)=O)C2)cc1>>CCN1C[C@@H](SCc2ccc(OC)cc2)C[C@H]1C(N)=O | C([O-])(O)=O.[Na+].C(C)I.C([O-])(O)=O.[Na+].C(N)(=O)[C@H]1NC[C@H](C1)SCC1=CC=C(C=C1)OC>>C(N)(=O)[C@H]1N(C[C@H](C1)SCC1=CC=C(C=C1)OC)CC | I[CH2:2][CH3:1].[NH:3]1[CH2:4][C@@H:5]([S:6][CH2:7][c:8]2[cH:9][cH:10][c:11]([O:12][CH3:13])[cH:14][cH:15]2)[CH2:16][C@H:17]1[C:18]([NH2:19])=[O:20]>>[CH3:1][CH2:2][N:3]1[CH2:4][C@@H:5]([S:6][CH2:7][c:8]2[cH:9][cH:10][c:11]([O:12][CH3:13])[cH:14][cH:15]2)[CH2:16][C@H:17]1[C:18]([NH2:19])=[O:20] | CCI.COc1ccc(CS[C@@H]2CN[C@H](C(N)=O)C2)cc1 | CCN1C[C@@H](SCc2ccc(OC)cc2)C[C@H]1C(N)=O | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 19b442dc26882f89f7423416f5e0a16bdb8e48776df57991434a0634e21f0505 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CS[C@H]2CCNC2)cc1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[N;D1;H2:3]-[C:4](=[O;D1;H0:5])-[C:6]1-[C:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[C;D1;H3:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[C:7]-[C:6]-1-[C:4](-[N;D1;H2:3])=[O;D1;H0:5] | null | [] | null | null | 5.5 | HOUR | 0.362 ml of ethyl iodide and 315 mg of sodium bicarbonate to a solution of 1000 mg of (2S, 4S)-2-carbamoyl-4-(4-methoxybenzylthio)pyrrolidine dissolved in 10 ml of dry dimethylformamide were added, whilst ice-cooling, and the mixture was stirred at room temperature for 5.5 hours. At the end of this time, the reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1 | HI | CN(C=O)C | null | 5.5 | CCI.COc1ccc(CS[C@@H]2CN[C@H](C(N)=O)C2)cc1>CN(C=O)C>CCN1C[C@@H](SCc2ccc(OC)cc2)C[C@H]1C(N)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a5b1c749d52b4210bf94b632a060afa3 | CCN1C[C@@H](SCc2ccc(OC)cc2)C[C@H]1C(N)=O.COS(=O)(=O)F>>CC[N+]1(C)C[C@@H](SCc2ccc(OC)cc2)C[C@H]1C(N)=O.O=S(=O)([O-])F | FS(=O)(=O)OC.C(N)(=O)[C@H]1N(C[C@H](C1)SCC1=CC=C(C=C1)OC)CC>>FS(=O)(=O)[O-].C(N)(=O)[C@H]1[N+](C[C@H](C1)SCC1=CC=C(C=C1)OC)(C)CC | [CH3:1][CH2:2][N:3]1[CH2:5][C@@H:6]([S:7][CH2:8][c:9]2[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16]2)[CH2:17][C@H:18]1[C:19]([NH2:20])=[O:21].[CH3:4][O:25][S:23](=[O:22])(=[O:24])[F:26]>>[CH3:1][CH2:2][N+:3]1([CH3:4])[CH2:5][C@@H:6]([S:7][CH2:8][c:9]2[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16]2)[CH2:17][C@H... | CCN1C[C@@H](SCc2ccc(OC)cc2)C[C@H]1C(N)=O.COS(=O)(=O)F | CC[N+]1(C)C[C@@H](SCc2ccc(OC)cc2)C[C@H]1C(N)=O.O=S(=O)([O-])F | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 5f722cf633dcf9b31e6556ed21943419798499e4b62ddaf4985fd6638a78aed4 | 5a8d30abc7481f1c446ec3891ae2e6d38df9cf7a08165b843f1d24fc50c4b9cd | c1ccc(CS[C@H]2CC[NH2+]C2)cc1 | [C;D1;H3:1]-[C:2]-[N;H0;D3;+0:3]1-[C:4]-[C:5]-[C:6]-[C:7]-1-[C:8](-[N;D1;H2:9])=[O;D1;H0:10].[CH3;D1;+0:11]-[O;H0;D2;+0:12]-[#16:13](-[F;D1;H0:14])(=[O;D1;H0:15])=[O;D1;H0:16]>>[C;D1;H3:1]-[C:2]-[N+;H0;D4:3]1(-[CH3;D1;+0:11])-[C:4]-[C:5]-[C:6]-[C:7]-1-[C:8](-[N;D1;H2:9])=[O;D1;H0:10].[F;D1;H0:14]-[#16:13](-[O-;H0;D1:12... | null | [] | null | null | 2 | HOUR | 0.43 ml of methyl fluorosulfonate was added, whilst ice-cooling, to a solution of 1.44 g of (2S, 4S)-2-carbamoyl-4-(4-methoxybenzylthio)-1-ethylpyrrolidine dissolved in 30 ml of dry methylene chloride and the mixture was stirred at room temperature for 2 hours. At the end of this time, the solvent was removed by distil... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | C1CC[NH]C1 | C1CC[NH+]C1 | C1CC[NH+]C1.c1ccccc1 | null | C(Cl)Cl | null | 2 | CCN1C[C@@H](SCc2ccc(OC)cc2)C[C@H]1C(N)=O.COS(=O)(=O)F>C(Cl)Cl>CC[N+]1(C)C[C@@H](SCc2ccc(OC)cc2)C[C@H]1C(N)=O.O=S(=O)([O-])F |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-33c9f6ab5a574eb69e32dd61abca60bf | CC(C)(C)OC(=O)N1C[C@@H](O)C[C@H]1C(=O)O.CCN>>CCNC(=O)[C@@H]1C[C@H](O)CN1C(=O)OC(C)(C)C | [Cl-].[Na+].ClC(=O)OCC.C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)O)C(=O)O.C(C)N>>C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)O)C(NCC)=O | O[C:4](=[O:5])[C@@H:6]1[CH2:7][C@H:8]([OH:9])[CH2:10][N:11]1[C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18].[CH3:1][CH2:2][NH2:3]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[C@@H:6]1[CH2:7][C@H:8]([OH:9])[CH2:10][N:11]1[C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18] | CC(C)(C)OC(=O)N1C[C@@H](O)C[C@H]1C(=O)O.CCN | CCNC(=O)[C@@H]1C[C@H](O)CN1C(=O)OC(C)(C)C | null | null | O1CCCC1.C(C)N(CC)CC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | C1CCNC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C:13].[C;D1;H3:14]-[C:15]-[NH2;D1;+0:16]>>[C:13]-[#7:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:16]-[C:15... | null | [] | null | null | 30 | MINUTE | 15.25 ml of triethylamine and subsequently a solution of 10.48 ml of ethyl chloroformate in 50 ml of dry tetrahydrofuran were added at -25° C. to a solution of 23.13 g of (2S, 4S)-1-t-butoxycarbonyl-4-hydroxy-2-pyrrolidinecarboxylic acid dissolved in 350 ml of dry tetrahydrofuran, and the mixture was stirred at the sam... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CC[NH]C1 | HO- | O1CCCC1.C(C)N(CC)CC | null | 0.5 | CC(C)(C)OC(=O)N1C[C@@H](O)C[C@H]1C(=O)O.CCN>O1CCCC1.C(C)N(CC)CC>CCNC(=O)[C@@H]1C[C@H](O)CN1C(=O)OC(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f4c935bb908045d3944dae4cba5fcbe4 | CCNC(=O)[C@@H]1C[C@H](O)CN1C(=O)OC(C)(C)C.CS(=O)(=O)Cl>>CCNC(=O)[C@@H]1C[C@H](OS(C)(=O)=O)CN1C(=O)OC(C)(C)C | [Cl-].[Na+].C(C)N(CC)CC.CS(=O)(=O)Cl.C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)O)C(NCC)=O>>C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)OS(=O)(=O)C)C(NCC)=O | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[C@@H:6]1[CH2:7][C@H:8]([OH:9])[CH2:14][N:15]1[C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22].Cl[S:10]([CH3:11])(=[O:12])=[O:13]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[C@@H:6]1[CH2:7][C@H:8]([O:9][S:10]([CH3:11])(=[O:12])=[O:13])[CH2:14][N:15]1[C:16](=[O:17])[O:18][C:19]([CH3:20])([... | CCNC(=O)[C@@H]1C[C@H](O)CN1C(=O)OC(C)(C)C.CS(=O)(=O)Cl | CCNC(=O)[C@@H]1C[C@H](OS(C)(=O)=O)CN1C(=O)OC(C)(C)C | null | null | O1CCCC1 | Acylation | Formation of Sulfonic Esters | 641955d0081c80f158ce2aacd31873a3f3301c87ca0800cf263e288ba8390217 | 4f9373df8a11470603daf885a5777cebf95940370e32739263d35df0f171a0dd | C1CCNC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#7:5]-[C:6]-[C:7](-[OH;D1;+0:8])-[C:9]>>[#7:5]-[C:6]-[C:7](-[O;H0;D2;+0:8]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])-[C:9] | null | [] | null | null | 30 | MINUTE | 13.81 ml of triethylamine and subsequently 7.65 ml of methanesulfonyl chloride were added, whilst ice-cooling, to a solution of 23.20 g of (2S, 4S)-1-t-butoxycarbonyl-2-ethylcarbamoyl-4-hydroxypyrrolidine dissolved in 250 ml of dry tetrahydrofuran, and then the mixture was stirred at 0° to 5° C. for 30 minutes. The rea... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Sulfonyl halide | Mesylate | null | null | C1CC[NH]C1 | HCl | O1CCCC1 | null | 0.5 | CCNC(=O)[C@@H]1C[C@H](O)CN1C(=O)OC(C)(C)C.CS(=O)(=O)Cl>O1CCCC1>CCNC(=O)[C@@H]1C[C@H](OS(C)(=O)=O)CN1C(=O)OC(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e3e33179047c45a592d53de6df46caae | CCNC(=O)[C@@H]1C[C@H](OS(C)(=O)=O)CN1C(=O)OC(C)(C)C.COc1ccc(CS)cc1>>CCNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C(=O)OC(C)(C)C | [Cl-].[Na+].[H-].[Na+].COC1=CC=C(CS)C=C1.C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)OS(=O)(=O)C)C(NCC)=O>>C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(NCC)=O | CS(=O)(=O)O[C@H:8]1[CH2:7][C@@H:6]([C:4]([NH:3][CH2:2][CH3:1])=[O:5])[N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:19]1.[SH:9][CH2:10][c:11]1[cH:12][cH:13][c:14]([O:15][CH3:16])[cH:17][cH:18]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[C@@H:6]1[CH2:7][C@H:8]([S:9][CH2:10][c:11]2[cH:12][cH:13][c:14]([O:15]... | CCNC(=O)[C@@H]1C[C@H](OS(C)(=O)=O)CN1C(=O)OC(C)(C)C.COc1ccc(CS)cc1 | CCNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C(=O)OC(C)(C)C | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | ea9de8eedcb8c3411962b7e96bdbc0799f2ed8fdff8f60ac6688856d164fc003 | 5d51471fb107f265fe2b725316ea74298d6b5b18b8910d02b969c8ad6fbd6b39 | c1ccc(CS[C@H]2CCNC2)cc1 | C-S(=O)(=O)-O-[C@@H;D3;+0:1]1-[C:2]-[#7:3](-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10])-[C:11](-[C:12](-[#7:13])=[O;D1;H0:14])-[C:15]-1.[SH;D1;+0:16]-[C:17]-[c:18]>>[#7:13]-[C:12](=[O;D1;H0:14])-[C:11]1-[C:15]-[C@H;D3;+0:1](-[S;H0;D2;+0:16]-[C:17]-[c:18])-[C:2]-[#7:3]-1-[C:4](=[O;D1;H0:5]... | null | [] | null | null | 30 | MINUTE | 3.57 g of sodium hydride (as a 55% w/w suspension in mineral oil) was added, whilst ice-cooling, to a solution of 11.31 ml of 4-methoxybenzyl mercaptan dissolved in 150 ml of dry dimethylformamide and the mixture was stirred at 0° to 5° C. for 30 minutes. A solution of 26.00 g of (2S, 4S)-1-t-butoxycarbonyl-2-ethylcarb... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aliphatic thiol | Monosulfide | C1CC[NH]C1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1 | MsOH.HO- | CN(C=O)C | null | 0.5 | CCNC(=O)[C@@H]1C[C@H](OS(C)(=O)=O)CN1C(=O)OC(C)(C)C.COc1ccc(CS)cc1>CN(C=O)C>CCNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C(=O)OC(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b7a72d018267442bb83530e1ef42bd9e | CCNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C(=O)OC(C)(C)C>>CCNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1 | Cl.C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(NCC)=O.C([O-])(O)=O.[Na+]>>C(C)NC(=O)[C@H]1NC[C@H](C1)SCC1=CC=C(C=C1)OC | CC(C)(C)OC(=O)[N:20]1[C@H:6]([C:4]([NH:3][CH2:2][CH3:1])=[O:5])[CH2:7][C@H:8]([S:9][CH2:10][c:11]2[cH:12][cH:13][c:14]([O:15][CH3:16])[cH:17][cH:18]2)[CH2:19]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[C@@H:6]1[CH2:7][C@H:8]([S:9][CH2:10][c:11]2[cH:12][cH:13][c:14]([O:15][CH3:16])[cH:17][cH:18]2)[CH2:19][NH:20]1 | CCNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C(=O)OC(C)(C)C | CCNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1 | null | null | C(C)(=O)OCC | Reduction | Boc amine deprotection | 7b506000be0005f6be41b2386b5bd6a8c45f704baa22d692d2f2ec984758e4ad | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(CS[C@H]2CCNC2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1-[C:6](=[O;D1;H0:7])-[#7:8]-[C:9]>>[C:9]-[#7:8]-[C:6](=[O;D1;H0:7])-[C:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | 82.5 | [{"value": 82.5, "product": "C(C)NC(=O)[C@H]1NC[C@H](C1)SCC1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 41.19 ml of a 4N ethyl acetate solution of hydrogen chloride were added to a solution of 13.00 g of (2S, 4S)-1-t-butoxycarbonyl-2-ethylcarbamoyl-4-(4-methoxybenzylthio)pyrrolidine dissolved in 100 ml of ethyl acetate, and the mixture was stirred at room temperature for 3 hours. At the end of this time, the reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]C1 | C1CCNC1 | C1CCNC1.c1ccccc1 | HO- | C(C)(=O)OCC | null | 3 | CCNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C(=O)OC(C)(C)C>C(C)(=O)OCC>CCNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-07dfe390ff4e442aa0fab0ba3b5fab07 | CCI.CCNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1>>CCNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1CC | [Cl-].[Na+].C(C)I.C([O-])(O)=O.[Na+].C(C)NC(=O)[C@H]1NC[C@H](C1)SCC1=CC=C(C=C1)OC>>C(C)NC(=O)[C@H]1N(C[C@H](C1)SCC1=CC=C(C=C1)OC)CC | I[CH2:21][CH3:22].[CH3:1][CH2:2][NH:3][C:4](=[O:5])[C@@H:6]1[CH2:7][C@H:8]([S:9][CH2:10][c:11]2[cH:12][cH:13][c:14]([O:15][CH3:16])[cH:17][cH:18]2)[CH2:19][NH:20]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[C@@H:6]1[CH2:7][C@H:8]([S:9][CH2:10][c:11]2[cH:12][cH:13][c:14]([O:15][CH3:16])[cH:17][cH:18]2)[CH2:19][N:20]1[CH2:21][CH... | CCI.CCNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1 | CCNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1CC | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 19b442dc26882f89f7423416f5e0a16bdb8e48776df57991434a0634e21f0505 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CS[C@H]2CCNC2)cc1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[C:3]-[#7:4]-[C:5](=[O;D1;H0:6])-[C:7]1-[C:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[C:3]-[#7:4]-[C:5](=[O;D1;H0:6])-[C:7]1-[C:8]-[C:9]-[C:10]-[N;H0;D3;+0:11]-1-[CH2;D2;+0:1]-[C;D1;H3:2] | null | [] | null | null | 5 | HOUR | 301 μl of ethyl iodide and 314 mg of sodium bicarbonate were added, whilst ice-cooling, to a solution of 1.00 g of (2S, 4S)-2-ethylcarbamoyl-4-(4-methoxybenzylthio)pyrrolidine dissolved in 8 ml of dry dimethylformamide, and the mixture was stirred at room temperature for 5 hours. At the end of this time, the reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1 | HI | CN(C=O)C | null | 5 | CCI.CCNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1>CN(C=O)C>CCNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1CC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a8f8a3b32f32483890fe4ab467777b15 | CCNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1CC.COS(=O)(=O)F>>CCNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)C[N+]1(C)CC.O=S(=O)([O-])F | FS(=O)(=O)OC.C(C)NC(=O)[C@H]1N(C[C@H](C1)SCC1=CC=C(C=C1)OC)CC>>FS(=O)(=O)[O-].C(C)NC(=O)[C@H]1[N+](C[C@H](C1)SCC1=CC=C(C=C1)OC)(C)CC | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[C@@H:6]1[CH2:7][C@H:8]([S:9][CH2:10][c:11]2[cH:12][cH:13][c:14]([O:15][CH3:16])[cH:17][cH:18]2)[CH2:19][N:20]1[CH2:22][CH3:23].[CH3:21][O:27][S:25](=[O:24])(=[O:26])[F:28]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[C@@H:6]1[CH2:7][C@H:8]([S:9][CH2:10][c:11]2[cH:12][cH:13][c:14]([O:15][CH3:16])... | CCNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1CC.COS(=O)(=O)F | CCNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)C[N+]1(C)CC.O=S(=O)([O-])F | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 5f722cf633dcf9b31e6556ed21943419798499e4b62ddaf4985fd6638a78aed4 | 5a8d30abc7481f1c446ec3891ae2e6d38df9cf7a08165b843f1d24fc50c4b9cd | c1ccc(CS[C@H]2CC[NH2+]C2)cc1 | [CH3;D1;+0:1]-[O;H0;D2;+0:2]-[#16:3](-[F;D1;H0:4])(=[O;D1;H0:5])=[O;D1;H0:6].[C:7]-[#7:8]-[C:9](=[O;D1;H0:10])-[C:11]1-[C:12]-[C:13]-[C:14]-[N;H0;D3;+0:15]-1-[C:16]-[C;D1;H3:17]>>[C:7]-[#7:8]-[C:9](=[O;D1;H0:10])-[C:11]1-[C:12]-[C:13]-[C:14]-[N+;H0;D4:15]-1(-[CH3;D1;+0:1])-[C:16]-[C;D1;H3:17].[F;D1;H0:4]-[#16:3](-[O-;H... | null | [] | null | null | 3.5 | HOUR | 233 μl of methyl fluorosulfonate were added, whilst ice-cooling, to a solution of 910 mg of (2S, 4S)-2-ethylcarbamoyl-1-ethyl-4-(4-methoxybenzylthio)pyrrolidine dissolved in 35 ml of dry methylene chloride, and the mixture was stirred at room temperature for 3.5 hours. At the end of this time, the solvent was removed b... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | C1CC[NH]C1 | C1CC[NH+]C1 | C1CC[NH+]C1.c1ccccc1 | null | C(Cl)Cl | null | 3.5 | CCNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1CC.COS(=O)(=O)F>C(Cl)Cl>CCNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)C[N+]1(C)CC.O=S(=O)([O-])F |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-bf4b72bd1c12477f9a2610f9db0493f3 | CCI.CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1>>CCN1C[C@@H](SCc2ccc(OC)cc2)C[C@H]1C(=O)NC | [Cl-].[Na+].C(C)I.C([O-])(O)=O.[Na+].COC1=CC=C(CS[C@H]2C[C@H](NC2)C(NC)=O)C=C1>>C(C)N1[C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(NC)=O | I[CH2:2][CH3:1].[NH:3]1[CH2:4][C@@H:5]([S:6][CH2:7][c:8]2[cH:9][cH:10][c:11]([O:12][CH3:13])[cH:14][cH:15]2)[CH2:16][C@H:17]1[C:18](=[O:19])[NH:20][CH3:21]>>[CH3:1][CH2:2][N:3]1[CH2:4][C@@H:5]([S:6][CH2:7][c:8]2[cH:9][cH:10][c:11]([O:12][CH3:13])[cH:14][cH:15]2)[CH2:16][C@H:17]1[C:18](=[O:19])[NH:20][CH3:21] | CCI.CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1 | CCN1C[C@@H](SCc2ccc(OC)cc2)C[C@H]1C(=O)NC | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 19b442dc26882f89f7423416f5e0a16bdb8e48776df57991434a0634e21f0505 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CS[C@H]2CCNC2)cc1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[C;D1;H3:3]-[#7:4]-[C:5](=[O;D1;H0:6])-[C:7]1-[C:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[C;D1;H3:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[C:8]-[C:7]-1-[C:5](=[O;D1;H0:6])-[#7:4]-[C;D1;H3:3] | null | [] | null | null | 1 | HOUR | 0.71 ml of ethyl iodide and 742 mg of sodium bicarbonate were added to a solution of 2.25 g of (2S, 4S)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine dissolved in 20 ml of dry dimethylformamide, and the mixture was stirred at 0° to 5° C. for 1 hour and then at room temperature for 5 hours. At the end of this tim... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1 | HI | CN(C=O)C | null | 1 | CCI.CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1>CN(C=O)C>CCN1C[C@@H](SCc2ccc(OC)cc2)C[C@H]1C(=O)NC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-429411c0a3c042dbbf0eb9f928ca4f75 | CCN1C[C@@H](SCc2ccc(OC)cc2)C[C@H]1C(=O)NC.COS(=O)(=O)F>>CC[N+]1(C)C[C@@H](SCc2ccc(OC)cc2)C[C@H]1C(=O)NC.O=S(=O)([O-])F | FS(=O)(=O)OC.C(C)N1[C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(NC)=O>>FS(=O)(=O)[O-].C(C)[N+]1([C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(NC)=O)C | [CH3:1][CH2:2][N:3]1[CH2:5][C@@H:6]([S:7][CH2:8][c:9]2[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16]2)[CH2:17][C@H:18]1[C:19](=[O:20])[NH:21][CH3:22].[CH3:4][O:26][S:24](=[O:23])(=[O:25])[F:27]>>[CH3:1][CH2:2][N+:3]1([CH3:4])[CH2:5][C@@H:6]([S:7][CH2:8][c:9]2[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16]2)[CH2:... | CCN1C[C@@H](SCc2ccc(OC)cc2)C[C@H]1C(=O)NC.COS(=O)(=O)F | CC[N+]1(C)C[C@@H](SCc2ccc(OC)cc2)C[C@H]1C(=O)NC.O=S(=O)([O-])F | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 5f722cf633dcf9b31e6556ed21943419798499e4b62ddaf4985fd6638a78aed4 | 5a8d30abc7481f1c446ec3891ae2e6d38df9cf7a08165b843f1d24fc50c4b9cd | c1ccc(CS[C@H]2CC[NH2+]C2)cc1 | [C;D1;H3:1]-[C:2]-[N;H0;D3;+0:3]1-[C:4]-[C:5]-[C:6]-[C:7]-1-[C:8](=[O;D1;H0:9])-[#7:10]-[C;D1;H3:11].[CH3;D1;+0:12]-[O;H0;D2;+0:13]-[#16:14](-[F;D1;H0:15])(=[O;D1;H0:16])=[O;D1;H0:17]>>[C;D1;H3:1]-[C:2]-[N+;H0;D4:3]1(-[CH3;D1;+0:12])-[C:4]-[C:5]-[C:6]-[C:7]-1-[C:8](=[O;D1;H0:9])-[#7:10]-[C;D1;H3:11].[F;D1;H0:15]-[#16:1... | null | [] | null | null | 4 | HOUR | 187 μl of methyl fluorosulfonate were added, whilst ice-cooling, to a solution of 700 mg of (2S, 4S)-1-ethyl-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine dissolved in 30 ml of dry methylene chloride, and the mixture was stirred at room temperature for 4 hours. At the end of this time, the solvent was removed by... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | C1CC[NH]C1 | C1CC[NH+]C1 | C1CC[NH+]C1.c1ccccc1 | null | C(Cl)Cl | null | 4 | CCN1C[C@@H](SCc2ccc(OC)cc2)C[C@H]1C(=O)NC.COS(=O)(=O)F>C(Cl)Cl>CC[N+]1(C)C[C@@H](SCc2ccc(OC)cc2)C[C@H]1C(=O)NC.O=S(=O)([O-])F |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0396738389f34b4993d50a9f35e708e2 | C=O.CCNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1>>CCNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C | C=O.C(#N)[BH3-].[Na+].C(C)NC(=O)[C@H]1NC[C@H](C1)SCC1=CC=C(C=C1)OC.[Cl-].[Na+].[OH-].[Na+]>>C(C)NC(=O)[C@H]1N(C[C@H](C1)SCC1=CC=C(C=C1)OC)C | O=[CH2:21].[CH3:1][CH2:2][NH:3][C:4](=[O:5])[C@@H:6]1[CH2:7][C@H:8]([S:9][CH2:10][c:11]2[cH:12][cH:13][c:14]([O:15][CH3:16])[cH:17][cH:18]2)[CH2:19][NH:20]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[C@@H:6]1[CH2:7][C@H:8]([S:9][CH2:10][c:11]2[cH:12][cH:13][c:14]([O:15][CH3:16])[cH:17][cH:18]2)[CH2:19][N:20]1[CH3:21] | C=O.CCNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1 | CCNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Secondary Amine Methylation | 91bb2ea8aeb046c2c7c6bbf5485a7fce0a359aeb3adea3549d5b06757bc9a669 | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | c1ccc(CS[C@H]2CCNC2)cc1 | O=[CH2;D1;+0:1].[C:2]-[#7:3]-[C:4](=[O;D1;H0:5])-[C:6]1-[C:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[C:2]-[#7:3]-[C:4](=[O;D1;H0:5])-[C:6]1-[C:7]-[C:8]-[C:9]-[N;H0;D3;+0:10]-1-[CH3;D1;+0:1] | 78.1 | [{"value": 78.1, "product": "C(C)NC(=O)[C@H]1N(C[C@H](C1)SCC1=CC=C(C=C1)OC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 40 | MINUTE | 3.43 ml of 35% formalin and 804 mg of sodium cyanoborohydride were added to a solution of 2.36 g of (2S, 4S)-2-ethylcarbamoyl-4-(4-methoxybenzylthio)-pyrrolidine dissolved in 42 ml of acetonitrile, and the mixture was stirred at room temperature for 40 minutes. At the end of this time, a 1N aqueous solution of sodium h... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1 | Other | C(C)#N | null | 0.666667 | C=O.CCNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1>C(C)#N>CCNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-af1ce96835f14d878c2d09702c43634d | CC(C)(C)OC(=O)N1CCC[C@H]1COS(C)(=O)=O.COc1ccc(CS)cc1>>COc1ccc(CSC[C@@H]2CCCN2C(=O)OC(C)(C)C)cc1 | C(C)(C)(C)OC(=O)N1[C@@H](CCC1)CO.COC1=CC=C(CS)C=C1.[H-].[Na+].C(C)(C)(C)OC(=O)N1[C@@H](CCC1)COS(=O)(=O)C>>C(C)(C)(C)OC(=O)N1[C@@H](CCC1)CSCC1=CC=C(C=C1)OC | CS(=O)(=O)O[CH2:9][C@@H:10]1[CH2:11][CH2:12][CH2:13][N:14]1[C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][SH:8])[cH:22][cH:23]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][CH2:9][C@@H:10]2[CH2:11][CH2:12][CH2:13][N:14]2[C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3... | CC(C)(C)OC(=O)N1CCC[C@H]1COS(C)(=O)=O.COc1ccc(CS)cc1 | COc1ccc(CSC[C@@H]2CCCN2C(=O)OC(C)(C)C)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 5ef6153311053d1fb9aeb0863ac740df1693ec5dc2fd63b54be9bba291d50d91 | 5d51471fb107f265fe2b725316ea74298d6b5b18b8910d02b969c8ad6fbd6b39 | c1ccc(CSC[C@@H]2CCCN2)cc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[C:3])-[#7:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11])-[C:12].[SH;D1;+0:13]-[C:14]-[c:15]>>[C:3]-[C:2](-[CH2;D2;+0:1]-[S;H0;D2;+0:13]-[C:14]-[c:15])-[#7:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11])-[C:12] | null | [] | null | null | null | null | The procedure described in Preparation 5-(2) was repeated, but using 12.16 g of (2S)-1-t-butoxycarbonyl-2-methanesulfonyloxymethylpyrrolidine [prepared by the methanesulfonylation of (2S)-1-t-butoxycarbonyl-2-hydroxymethylpyrrolidine], 7.3 ml of 4-methoxybenzyl mercaptan and 2.3 g of sodium hydride (as a 55% w/w suspen... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aliphatic thiol | Monosulfide | null | null | c1ccccc1.C1CC[NH]C1 | MsOH.HO- | CN(C=O)C | null | null | CC(C)(C)OC(=O)N1CCC[C@H]1COS(C)(=O)=O.COc1ccc(CS)cc1>CN(C=O)C>COc1ccc(CSC[C@@H]2CCCN2C(=O)OC(C)(C)C)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1fc826cd6595419badb8308649438ba2 | C=O.COc1ccc(CSC[C@@H]2CCCN2)cc1>>COc1ccc(CSC[C@@H]2CCCN2C)cc1 | COC1=CC=C(CSC[C@H]2NCCC2)C=C1.C=O.C(#N)[BH3-].[Na+]>>COC1=CC=C(CSC[C@H]2N(CCC2)C)C=C1 | O=[CH2:15].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][CH2:9][C@@H:10]2[CH2:11][CH2:12][CH2:13][NH:14]2)[cH:16][cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][CH2:9][C@@H:10]2[CH2:11][CH2:12][CH2:13][N:14]2[CH3:15])[cH:16][cH:17]1 | C=O.COc1ccc(CSC[C@@H]2CCCN2)cc1 | COc1ccc(CSC[C@@H]2CCCN2C)cc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Secondary Amine Methylation | 91bb2ea8aeb046c2c7c6bbf5485a7fce0a359aeb3adea3549d5b06757bc9a669 | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | c1ccc(CSC[C@@H]2CCCN2)cc1 | O=[CH2;D1;+0:1].[C:2]-[C:3]1-[C:4]-[C:5]-[C:6]-[NH;D2;+0:7]-1>>[C:2]-[C:3]1-[C:4]-[C:5]-[C:6]-[N;H0;D3;+0:7]-1-[CH3;D1;+0:1] | 41.7 | [{"value": 41.7, "product": "COC1=CC=C(CSC[C@H]2N(CCC2)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure described in Preparation 5-(4) was repeated, but using 2 g of (2S)-2-(4-methoxybenzylthiomethyl)pyrrolidine, 35% formalin and 848 mg of sodium cyanoborohydride in the presence of 44 ml of acetonitrile, to afford 883 mg of the title compound as an oil.
Conditions: See reaction.notes.procedure_details.
Work... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | Other | C(C)#N | null | null | C=O.COc1ccc(CSC[C@@H]2CCCN2)cc1>C(C)#N>COc1ccc(CSC[C@@H]2CCCN2C)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5a0095e69f164f00815bcbd1c99cbbde | COS(=O)(=O)F.COc1ccc(CSC[C@@H]2CCCN2C)cc1>>COc1ccc(CSC[C@@H]2CCC[N+]2(C)C)cc1.O=S(=O)([O-])F | COC1=CC=C(CSC[C@H]2N(CCC2)C)C=C1.FS(=O)(=O)OC>>FS(=O)(=O)[O-].C[N+]1([C@@H](CCC1)CSCC1=CC=C(C=C1)OC)C | [CH3:16][O:22][S:20](=[O:19])(=[O:21])[F:23].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][CH2:9][C@@H:10]2[CH2:11][CH2:12][CH2:13][N:14]2[CH3:15])[cH:17][cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][CH2:9][C@@H:10]2[CH2:11][CH2:12][CH2:13][N+:14]2([CH3:15])[CH3:16])[cH:17][cH:18]1.[O:19]=[S:20](=[O:21]... | COS(=O)(=O)F.COc1ccc(CSC[C@@H]2CCCN2C)cc1 | COc1ccc(CSC[C@@H]2CCC[N+]2(C)C)cc1.O=S(=O)([O-])F | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 5f722cf633dcf9b31e6556ed21943419798499e4b62ddaf4985fd6638a78aed4 | 5a8d30abc7481f1c446ec3891ae2e6d38df9cf7a08165b843f1d24fc50c4b9cd | c1ccc(CSC[C@@H]2CCC[NH2+]2)cc1 | [CH3;D1;+0:1]-[O;H0;D2;+0:2]-[#16:3](-[F;D1;H0:4])(=[O;D1;H0:5])=[O;D1;H0:6].[C:7]-[C:8]1-[C:9]-[C:10]-[C:11]-[N;H0;D3;+0:12]-1-[C;D1;H3:13]>>[C:7]-[C:8]1-[C:9]-[C:10]-[C:11]-[N+;H0;D4:12]-1(-[C;D1;H3:13])-[CH3;D1;+0:1].[F;D1;H0:4]-[#16:3](-[O-;H0;D1:2])(=[O;D1;H0:5])=[O;D1;H0:6] | null | [] | null | null | null | null | The procedure described in Preparation 5-(5) was repeated, but using 740 mg of (2S)-2-(4-methoxybenzylthiomethyl)-1-methylpyrrolidine and 243 μl of methyl fluorosulfonate in the presence of 22 ml of methylene chloride, to afford 1.0 g of the title compound as crystals, melting at 150°-153° C.
Conditions: See reaction.n... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | C1CC[NH]C1 | C1CC[NH+]C1 | c1ccccc1.C1CC[NH+]C1 | null | C(Cl)Cl | null | null | COS(=O)(=O)F.COc1ccc(CSC[C@@H]2CCCN2C)cc1>C(Cl)Cl>COc1ccc(CSC[C@@H]2CCC[N+]2(C)C)cc1.O=S(=O)([O-])F |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-99664006be504064b5ebab627eb4824a | COc1ccc(CS[C@@H]2CN[C@H](C(N)=O)C2)cc1.OCCI>>COc1ccc(CS[C@H]2C[C@@H](C(N)=O)N(CCO)C2)cc1 | C([O-])(O)=O.[Na+].ICCO.C([O-])(O)=O.[Na+].C(N)(=O)[C@H]1NC[C@H](C1)SCC1=CC=C(C=C1)OC>>C(N)(=O)[C@H]1N(C[C@H](C1)SCC1=CC=C(C=C1)OC)CCO | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][C@H:9]2[CH2:10][C@@H:11]([C:12]([NH2:13])=[O:14])[NH:15][CH2:19]2)[cH:20][cH:21]1.I[CH2:16][CH2:17][OH:18]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][C@H:9]2[CH2:10][C@@H:11]([C:12]([NH2:13])=[O:14])[N:15]([CH2:16][CH2:17][OH:18])[CH2:19]2)[cH:20][cH:21]1 | COc1ccc(CS[C@@H]2CN[C@H](C(N)=O)C2)cc1.OCCI | COc1ccc(CS[C@H]2C[C@@H](C(N)=O)N(CCO)C2)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 19b442dc26882f89f7423416f5e0a16bdb8e48776df57991434a0634e21f0505 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CS[C@H]2CCNC2)cc1 | I-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3].[N;D1;H2:4]-[C:5](=[O;D1;H0:6])-[C:7]1-[C:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[N;D1;H2:4]-[C:5](=[O;D1;H0:6])-[C:7]1-[C:8]-[C:9]-[C:10]-[N;H0;D3;+0:11]-1-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3] | null | [] | null | null | 2.5 | HOUR | 0.175 ml of 2-iodoethanol and 0.16 g of sodium bicarbonate were added, whilst ice-cooling, to a solution of 0.5 g of (2S, 4S)-2-carbamoyl-4-(4-methoxybenzylthio)pyrrolidine [prepared as described in Preparation 1-(5)] dissolved in 5 ml of dry dimethylformamide, and the mixture was stirred at the same temperature for 1 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HI | CN(C=O)C | null | 2.5 | COc1ccc(CS[C@@H]2CN[C@H](C(N)=O)C2)cc1.OCCI>CN(C=O)C>COc1ccc(CS[C@H]2C[C@@H](C(N)=O)N(CCO)C2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c40fc1cfcee0401fbf2b804fba54c690 | COS(=O)(=O)F.COc1ccc(CS[C@H]2C[C@@H](C(N)=O)N(CCO)C2)cc1>>COc1ccc(CS[C@H]2C[C@@H](C(N)=O)[N+](C)(CCO)C2)cc1.O=S(=O)([O-])F | FS(=O)(=O)OC.C(N)(=O)[C@H]1N(C[C@H](C1)SCC1=CC=C(C=C1)OC)CCO>>FS(=O)(=O)[O-].C(N)(=O)[C@H]1[N+](C[C@H](C1)SCC1=CC=C(C=C1)OC)(C)CCO | [CH3:16][O:26][S:24](=[O:23])(=[O:25])[F:27].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][C@H:9]2[CH2:10][C@@H:11]([C:12]([NH2:13])=[O:14])[N:15]([CH2:17][CH2:18][OH:19])[CH2:20]2)[cH:21][cH:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][C@H:9]2[CH2:10][C@@H:11]([C:12]([NH2:13])=[O:14])[N+:15]([CH3:16])([CH... | COS(=O)(=O)F.COc1ccc(CS[C@H]2C[C@@H](C(N)=O)N(CCO)C2)cc1 | COc1ccc(CS[C@H]2C[C@@H](C(N)=O)[N+](C)(CCO)C2)cc1.O=S(=O)([O-])F | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 5f722cf633dcf9b31e6556ed21943419798499e4b62ddaf4985fd6638a78aed4 | 5a8d30abc7481f1c446ec3891ae2e6d38df9cf7a08165b843f1d24fc50c4b9cd | c1ccc(CS[C@H]2CC[NH2+]C2)cc1 | [CH3;D1;+0:1]-[O;H0;D2;+0:2]-[#16:3](-[F;D1;H0:4])(=[O;D1;H0:5])=[O;D1;H0:6].[C:7]-[C:8]-[N;H0;D3;+0:9]1-[C:10]-[C:11]-[C:12]-[C:13]-1-[C:14](-[N;D1;H2:15])=[O;D1;H0:16]>>[C:7]-[C:8]-[N+;H0;D4:9]1(-[CH3;D1;+0:1])-[C:10]-[C:11]-[C:12]-[C:13]-1-[C:14](-[N;D1;H2:15])=[O;D1;H0:16].[F;D1;H0:4]-[#16:3](-[O-;H0;D1:2])(=[O;D1;... | null | [] | null | null | 2 | HOUR | 0.108 ml of methyl fluorosulfonate was added dropwise at room temperature to a solution of 0.38 of (2S, 4S)-2-carbamoyl-1-(2-hydroxyethyl)-4-(4-methoxybenzylthio)pyrrolidine dissolved in 7.5 ml of dry methylene chloride, and the mixture was stirred at the same temperature for 2 hours. At the end of this time, the solve... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | C1CC[NH]C1 | C1CC[NH+]C1 | c1ccccc1.C1CC[NH+]C1 | null | C(Cl)Cl | null | 2 | COS(=O)(=O)F.COc1ccc(CS[C@H]2C[C@@H](C(N)=O)N(CCO)C2)cc1>C(Cl)Cl>COc1ccc(CS[C@H]2C[C@@H](C(N)=O)[N+](C)(CCO)C2)cc1.O=S(=O)([O-])F |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b1ecc63b5cfd4eac90d16e7b577321a5 | COc1ccc(CS)cc1.CS(=O)(=O)OC1CN2CCC1CC2>>COc1ccc(CSC2CN3CCC2CC3)cc1 | CS(=O)(=O)OC1CN2CCC1CC2.N12CC(C(CC1)CC2)O.COC1=CC=C(CS)C=C1.[H-].[Na+]>>COC1=CC=C(CSC2CN3CCC2CC3)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][SH:8])[cH:17][cH:18]1.CS(=O)(=O)O[CH:9]1[CH2:10][N:11]2[CH2:12][CH2:13][CH:14]1[CH2:15][CH2:16]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][CH:9]2[CH2:10][N:11]3[CH2:12][CH2:13][CH:14]2[CH2:15][CH2:16]3)[cH:17][cH:18]1 | COc1ccc(CS)cc1.CS(=O)(=O)OC1CN2CCC1CC2 | COc1ccc(CSC2CN3CCC2CC3)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 12d2c9ce2db156e052c3243e9c2a5b58d4f74efdfd9b520424868ea3c986288f | 5d51471fb107f265fe2b725316ea74298d6b5b18b8910d02b969c8ad6fbd6b39 | c1ccc(CSC2CN3CCC2CC3)cc1 | C-S(=O)(=O)-O-[CH;D3;+0:1]1-[C:2]-[#7:3]2-[C:4]-[C:5]-[C:6]-1-[C:7]-[C:8]-2.[SH;D1;+0:9]-[C:10]-[c:11]>>[c:11]-[C:10]-[S;H0;D2;+0:9]-[CH;D3;+0:1]1-[C:2]-[#7:3]2-[C:4]-[C:5]-[C:6]-1-[C:7]-[C:8]-2 | null | [] | null | null | null | null | The procedure described in Preparation 6-(2) was repeated, but using 3.7 g of 3-methanesulfonyloxyquinuclidine (prepared by the methanesulfonylation of 3-quinuclidinol), 3.0 ml of 4-methoxybenzyl mercaptan and 0.942 g of sodium hydride (as a 55% w/w suspension in mineral oil), to afford 1.74 g of the title compound as ... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aliphatic thiol | Monosulfide | C1CN2CCC1CC2 | C1CN2CCC1CC2 | c1ccccc1.C1CN2CCC1CC2 | MsOH.HO- | null | null | null | COc1ccc(CS)cc1.CS(=O)(=O)OC1CN2CCC1CC2>>COc1ccc(CSC2CN3CCC2CC3)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2f5f24183fd544bba8168c7d1c51e356 | COS(=O)(=O)F.COc1ccc(CSC2CN3CCC2CC3)cc1>>COc1ccc(CSC2C[N+]3(C)CCC2CC3)cc1.O=S(=O)([O-])F | COC1=CC=C(CSC2CN3CCC2CC3)C=C1.FS(=O)(=O)OC>>FS(=O)(=O)[O-].COC1=CC=C(CSC2C[N+]3(CCC2CC3)C)C=C1 | [CH3:12][O:23][S:21](=[O:20])(=[O:22])[F:24].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][CH:9]2[CH2:10][N:11]3[CH2:13][CH2:14][CH:15]2[CH2:16][CH2:17]3)[cH:18][cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][CH:9]2[CH2:10][N+:11]3([CH3:12])[CH2:13][CH2:14][CH:15]2[CH2:16][CH2:17]3)[cH:18][cH:19]1.[O:20]=... | COS(=O)(=O)F.COc1ccc(CSC2CN3CCC2CC3)cc1 | COc1ccc(CSC2C[N+]3(C)CCC2CC3)cc1.O=S(=O)([O-])F | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 4f219f8d05883cff5f9b3c02dabd46d48403e261e4b1908a6bde1cc75217ab51 | 5a8d30abc7481f1c446ec3891ae2e6d38df9cf7a08165b843f1d24fc50c4b9cd | c1ccc(CSC2C[NH+]3CCC2CC3)cc1 | [CH3;D1;+0:1]-[O;H0;D2;+0:2]-[#16:3](-[F;D1;H0:4])(=[O;D1;H0:5])=[O;D1;H0:6].[C:7]-[C:8]-[N;H0;D3;+0:9](-[C:10]-[C:11])-[C:12]-[C:13]>>[C:7]-[C:8]-[N+;H0;D4:9](-[CH3;D1;+0:1])(-[C:10]-[C:11])-[C:12]-[C:13].[F;D1;H0:4]-[#16:3](-[O-;H0;D1:2])(=[O;D1;H0:5])=[O;D1;H0:6] | null | [] | null | null | null | null | The procedure described in Preparation 6-(3) was repeated, but using 756 mg of 3-(4-methoxybenzylthio)-quinuclidine and 271 μl of methyl fluorosulfonate in the presence of 5 ml of methylene chloride, to afford 1.078 g of the title compound as an oil.
Conditions: See reaction.notes.procedure_details.
Workup: The procedu... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.C1C[NH+]2CCC1CC2 | null | C(Cl)Cl | null | null | COS(=O)(=O)F.COc1ccc(CSC2CN3CCC2CC3)cc1>C(Cl)Cl>COc1ccc(CSC2C[N+]3(C)CCC2CC3)cc1.O=S(=O)([O-])F |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c4d3c967ee794540a87c6456700647c8 | CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1.OCCI>>CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1CCO | [Cl-].[Na+].ICCO.C([O-])(O)=O.[Na+].COC1=CC=C(CS[C@H]2C[C@H](NC2)C(NC)=O)C=C1>>OCCN1[C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(NC)=O | [CH3:1][NH:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([S:8][CH2:9][c:10]2[cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17]2)[CH2:18][NH:19]1.I[CH2:20][CH2:21][OH:22]>>[CH3:1][NH:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([S:8][CH2:9][c:10]2[cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17]2)[CH2:18][N:19]1[CH2:20][CH2:21][OH:... | CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1.OCCI | CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1CCO | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 19b442dc26882f89f7423416f5e0a16bdb8e48776df57991434a0634e21f0505 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CS[C@H]2CCNC2)cc1 | I-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3].[C;D1;H3:4]-[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]1-[C:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[C;D1;H3:4]-[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]1-[C:9]-[C:10]-[C:11]-[N;H0;D3;+0:12]-1-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3] | null | [] | 40 | CELSIUS | 24 | HOUR | 934 μl of 2-iodoethanol and 1.01 g of sodium bicarbonate were added, whilst ice-cooling, to a solution of 2.80 g of (2S, 4S)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine dissolved in 18 ml of dry dimethylformamide, and the mixture was stirred at 40° C. for 24 hours. At the end of this time, the reaction mixture... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1 | HI | CN(C=O)C | 40 | 24 | CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1.OCCI>CN(C=O)C>CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1CCO |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c4ffa53c53ad4c46a62aa45858110c76 | CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1CCO.CS(=O)(=O)Cl>>CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1CCOS(C)(=O)=O | C(C)N(CC)CC.CS(=O)(=O)Cl.OCCN1[C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(NC)=O>>CS(=O)(=O)OCCN1[C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(NC)=O | [CH3:1][NH:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([S:8][CH2:9][c:10]2[cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17]2)[CH2:18][N:19]1[CH2:20][CH2:21][OH:22].Cl[S:23]([CH3:24])(=[O:25])=[O:26]>>[CH3:1][NH:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([S:8][CH2:9][c:10]2[cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17]2)[CH... | CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1CCO.CS(=O)(=O)Cl | CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1CCOS(C)(=O)=O | null | null | O1CCCC1 | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccc(CS[C@H]2CCNC2)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | 30 | MINUTE | 1.06 ml of triethylamine and subsequently 584 μl of methanesulfonyl chloride were added, whilst ice-cooling, to a solution of 2.13 g of (2S, 4S)-1-(2-hydroxyethyl)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine dissolved in 45 ml of dry tetrahydrofuran, and the mixture was stirred at 0° to 5° C. for 30 minutes. A... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | C1CC[NH]C1.c1ccccc1 | HCl | O1CCCC1 | null | 0.5 | CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1CCO.CS(=O)(=O)Cl>O1CCCC1>CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1CCOS(C)(=O)=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f71993a5c79649908460f68d8e688e89 | CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1CCOS(C)(=O)=O>>COc1ccc(CS[C@H]2C[C@H]3C(=O)N(C)CCN3C2)cc1 | [H-].[Na+].CS(=O)(=O)OCCN1[C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(NC)=O.[Cl-].[Na+]>>COC1=CC=C(CS[C@H]2C[C@H]3C(N(CCN3C2)C)=O)C=C1 | CS(=O)(=O)O[CH2:16][CH2:17][N:18]1[C@H:11]([C:12](=[O:13])[NH:14][CH3:15])[CH2:10][C@H:9]([S:8][CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:21][cH:20]2)[CH2:19]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][C@H:9]2[CH2:10][C@H:11]3[C:12](=[O:13])[N:14]([CH3:15])[CH2:16][CH2:17][N:18]3[CH2:19]2)[cH:20][cH:21]1 | CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1CCOS(C)(=O)=O | COc1ccc(CS[C@H]2C[C@H]3C(=O)N(C)CCN3C2)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 06b365dc73d8611bd2940c9777a90100f418aba6e2794bad1d5a3f27c0412a22 | bf4a9d4c770f1494b23021dd5ba99337e3cf1b7c91121f136ba60734118ef0d9 | O=C1NCCN2C[C@@H](SCc3ccccc3)C[C@@H]12 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[#7:3]-[C:4]-[C:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[C;D1;H3:8]>>[C;D1;H3:8]-[N;H0;D3;+0:7]1-[CH2;D2;+0:1]-[C:2]-[#7:3]-[C:4]-[C:5]-1=[O;D1;H0:6] | 87.1 | [{"value": 87.1, "product": "COC1=CC=C(CS[C@H]2C[C@H]3C(N(CCN3C2)C)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 347 mg of sodium hydride (as a 55% w/w suspension in mineral oil) was added, whilst ice-cooling, to a solution of 2.64 g of (2S, 4S)-1-(2-methanesulfonyloxyethyl)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine dissolved in 30 ml of dry dimethylformamide, and the mixture was stirred at 0° to 5° C. for 30 minutes a... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amide | Tertiary amide | null | C1C[C@H]2C[NH]CCN2C1 | c1ccccc1.C1C[C@H]2C[NH]CCN2C1 | MsOH.HO- | CN(C=O)C | null | 0.5 | CNC(=O)[C@@H]1C[C@H](SCc2ccc(OC)cc2)CN1CCOS(C)(=O)=O>CN(C=O)C>COc1ccc(CS[C@H]2C[C@H]3C(=O)N(C)CCN3C2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-af6090bbcc8144a0a01582239a197438 | COS(=O)(=O)F.COc1ccc(CS[C@H]2C[C@H]3C(=O)N(C)CCN3C2)cc1>>COc1ccc(CS[C@H]2C[C@H]3C(=O)N(C)CC[N+]3(C)C2)cc1.O=S(=O)([O-])F | FS(=O)(=O)OC.COC1=CC=C(CS[C@H]2C[C@H]3C(N(CCN3C2)C)=O)C=C1>>FS(=O)(=O)[O-].C[N+]12CCN(C([C@@H]2C[C@@H](C1)SCC1=CC=C(C=C1)OC)=O)C | [CH3:19][O:26][S:24](=[O:23])(=[O:25])[F:27].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][C@H:9]2[CH2:10][C@H:11]3[C:12](=[O:13])[N:14]([CH3:15])[CH2:16][CH2:17][N:18]3[CH2:20]2)[cH:21][cH:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][C@H:9]2[CH2:10][C@H:11]3[C:12](=[O:13])[N:14]([CH3:15])[CH2:16][CH2:17][... | COS(=O)(=O)F.COc1ccc(CS[C@H]2C[C@H]3C(=O)N(C)CCN3C2)cc1 | COc1ccc(CS[C@H]2C[C@H]3C(=O)N(C)CC[N+]3(C)C2)cc1.O=S(=O)([O-])F | null | null | C(Cl)Cl.C(C)OCC | Functional Group Interconversion | OtherReaction | cd15ec4cddade7181be9b420affa8d3c16a8fdf5568f74f371a7a30df8846861 | 5a8d30abc7481f1c446ec3891ae2e6d38df9cf7a08165b843f1d24fc50c4b9cd | O=C1NCC[NH+]2C[C@@H](SCc3ccccc3)C[C@@H]12 | [C;D1;H3:1]-[#7:2]1-[C:3]-[C:4]-[N;H0;D3;+0:5]2-[C:6]-[C:7]-[C:8]-[C:9]-2-[C:10]-1=[O;D1;H0:11].[CH3;D1;+0:12]-[O;H0;D2;+0:13]-[#16:14](-[F;D1;H0:15])(=[O;D1;H0:16])=[O;D1;H0:17]>>[C;D1;H3:1]-[#7:2]1-[C:3]-[C:4]-[N+;H0;D4:5]2(-[CH3;D1;+0:12])-[C:6]-[C:7]-[C:8]-[C:9]-2-[C:10]-1=[O;D1;H0:11].[F;D1;H0:15]-[#16:14](-[O-;H0... | null | [] | null | null | 2 | HOUR | 461 μl of methyl fluorosulfonate was added, whilst ice-cooling, to a solution of 1.71 g of (6S, 8S)-8-(4-methoxybenzylthio)-4-methyl-5-oxo-1,4-diazabicyclo-[4.3.0]nonane dissolved in 60 ml of methylene chloride, and the mixture was stirred at room temperature for 2 hours. At the end of this time, the mixture was dilute... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | C1C[C@H]2C[NH]CCN2C1 | C1C[C@H]2C[NH]CC[NH+]2C1 | c1ccccc1.C1C[C@H]2C[NH]CC[NH+]2C1 | null | C(Cl)Cl.C(C)OCC | null | 2 | COS(=O)(=O)F.COc1ccc(CS[C@H]2C[C@H]3C(=O)N(C)CCN3C2)cc1>C(Cl)Cl.C(C)OCC>COc1ccc(CS[C@H]2C[C@H]3C(=O)N(C)CC[N+]3(C)C2)cc1.O=S(=O)([O-])F |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-715795a169ab49eca88ae924fb7a34b7 | COc1ccc(CSC2CCNC2=O)cc1>>O=C1NCCC1S | FC(C(=O)O)(F)F.FC(S(=O)(=O)O)(F)F.COC1=CC=C(CSC2C(NCC2)=O)C=C1>>FC(S(=O)(=O)O)(F)F.SC1C(NCC1)=O | COc1ccc(C[S:7][CH:6]2[C:2](=[O:1])[NH:3][CH2:4][CH2:5]2)cc1>>[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][CH:6]1[SH:7] | COc1ccc(CSC2CCNC2=O)cc1 | O=C1NCCC1S | null | null | C1(=CC=CC=C1)OC | Reduction | OtherReaction | ed84898b1491eef4fb5ae56217720ec9f79d8f2f338f79337659a31bf800b5c8 | 3d06aaadf2d797a77b14c78cb9b213103f90ff2ed2c0041114d44574ec9e95ff | O=C1CCCN1 | C-O-c1:c:c:c(-C-[S;H0;D2;+0:1]-[C:2]2-[C:3]-[C:4]-[#7:5]-[C:6]-2=[O;D1;H0:7]):c:c:1>>[O;D1;H0:7]=[C:6]1-[#7:5]-[C:4]-[C:3]-[C:2]-1-[SH;D1;+0:1] | null | [] | null | null | 30 | MINUTE | 20 ml of trifluoroacetic acid and 0.41 ml of trifluoromethanesulfonic acid were added, whilst ice-cooling, to a solution of 949 mg of 3-(4-methoxybenzylthio)pyrrolidin-2-one in 4 ml of anisole, and then the mixture was stirred at room temperature for 30 minutes. At the end of this time, the reaction mixture was concent... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Monosulfide | Aliphatic thiol | c1ccccc1 | null | C1CCNC1 | HO- | C1(=CC=CC=C1)OC | null | 0.5 | COc1ccc(CSC2CCNC2=O)cc1>C1(=CC=CC=C1)OC>O=C1NCCC1S |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-68f86829b5d7433a974d30f73e142209 | CC(O)=S.O=C1CC(O)CN1>>CC(=O)SC1CNC(=O)C1 | C(C)(=S)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.OC1CC(NC1)=O.N(=NC(=O)OCC)C(=O)OCC>>C(C)(=O)SC1CC(NC1)=O | [CH3:1][C:2]([OH:3])=[S:4].O[CH:5]1[CH2:6][NH:7][C:8](=[O:9])[CH2:10]1>>[CH3:1][C:2](=[O:3])[S:4][CH:5]1[CH2:6][NH:7][C:8](=[O:9])[CH2:10]1 | CC(O)=S.O=C1CC(O)CN1 | CC(=O)SC1CNC(=O)C1 | null | null | O1CCCC1 | Acylation | OtherReaction | 97335de197d0b88a77fb11626d93cc521365e3acabd9242a0b7b38dff57d49b0 | 9c6158e091845973f5238be0a77db6550cf525792cb3b6de11213355918eda13 | O=C1CCCN1 | O-[CH;D3;+0:1]1-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[C:6]-1.[C;D1;H3:7]-[C;H0;D3;+0:8](-[OH;D1;+0:9])=[S;H0;D1;+0:10]>>[C;D1;H3:7]-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[S;H0;D2;+0:10]-[CH;D3;+0:1]1-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[C:6]-1 | null | [] | null | null | 5 | MINUTE | 20-(1) 15.6 g of triphenylphosphine were added to a suspension of 3 g of 4-hydroxy-2-pyrrolidinone in 200 ml of tetrahydrofuran, and then the mixture was stirred at room temperature for 5 minutes, after which it was cooled to -20° C. A solution of 9.3 ml of diethyl azodicarboxylate in 9 ml of tetrahydrofuran was added ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Thiocarbonyl | Carbo-thioester | C1CCNC1 | C1CCNC1 | C1CCNC1 | HO- | O1CCCC1 | null | 0.083333 | CC(O)=S.O=C1CC(O)CN1>O1CCCC1>CC(=O)SC1CNC(=O)C1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-909f6e9c98fd499ca582667d47b75e98 | CN(C)C=O.COc1cccc(Cl)n1>>COc1nc(Cl)ccc1C=O | C(C)(=O)O.CN(C=O)C.C(C)(C)(C)[Li].ClC1=CC=CC(=N1)OC>>ClC1=CC=C(C(=N1)OC)C=O | CN(C)[CH:10]=[O:11].[CH3:1][O:2][c:3]1[n:4][c:5]([Cl:6])[cH:7][cH:8][cH:9]1>>[CH3:1][O:2][c:3]1[n:4][c:5]([Cl:6])[cH:7][cH:8][c:9]1[CH:10]=[O:11] | CN(C)C=O.COc1cccc(Cl)n1 | COc1nc(Cl)ccc1C=O | null | null | CCOCC.C1CCOC1 | C-C Coupling | OtherReaction | fdadf445bc7330d90b7bd9b20fa76e9137f072d7efd4f8187f2f956f7d29eb78 | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccncc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[#8:3]-[c:4]1:[#7;a:5]:[c:6]:[c:7]:[c:8]:[cH;D2;+0:9]:1>>[#8:3]-[c:4]1:[#7;a:5]:[c:6]:[c:7]:[c:8]:[c;H0;D3;+0:9]:1-[CH;D2;+0:1]=[O;D1;H0:2] | 75 | [{"value": 75.0, "product": "ClC1=CC=C(C(=N1)OC)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.6, "product": "ClC1=CC=C(C(=N1)OC)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 1 | HOUR | To a solution of tert-butyllithium (1.7M in pentane, 48.5 mL, 83.0 mmol) in 150 mL of THF at -78° C. was added 6-chloro-2-methoxypyridine (8.94 mL, 75.0 mmol) over 5 min. The reaction mixture was stirred at -78° C. for 1 h, then dimethylformamide (7.55 mL, 97 mmol) was added and the mixture was stirred at this temperat... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1ccncc1 | c1ccncc1 | c1ccncc1 | Other | CCOCC.C1CCOC1 | -78 | 1 | CN(C)C=O.COc1cccc(Cl)n1>CCOCC.C1CCOC1>COc1nc(Cl)ccc1C=O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-aeb93de1e4c4434bb6bea2d3b209f39a | COc1nc(Cl)ccc1C=O.II>>COc1nc(Cl)cc(I)c1C=O | II.ClC1=CC=C(C(=N1)OC)C=O.[Li]CCCC.CN(CCNC)C.[Li]CCCC>>ClC1=CC(=C(C(=N1)OC)C=O)I | [CH3:1][O:2][c:3]1[n:4][c:5]([Cl:6])[cH:7][cH:8][c:10]1[CH:11]=[O:12].I[I:9]>>[CH3:1][O:2][c:3]1[n:4][c:5]([Cl:6])[cH:7][c:8]([I:9])[c:10]1[CH:11]=[O:12] | COc1nc(Cl)ccc1C=O.II | COc1nc(Cl)cc(I)c1C=O | null | null | COCCOC | Functional Group Interconversion | OtherReaction | 66a492ff31bfcbb52d9a760416ba269a4cf5a439a6c2ca9c2c3a3ed0a750b974 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccncc1 | I-[I;H0;D1;+0:1].[#8:2]-[c:3]1:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:[cH;D2;+0:8]:[c:9]:1-[C:10]=[O;D1;H0:11]>>[#8:2]-[c:3]1:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:[c;H0;D3;+0:8](-[I;H0;D1;+0:1]):[c:9]:1-[C:10]=[O;D1;H0:11] | 51.3 | [{"value": 51.3, "product": "ClC1=CC(=C(C(=N1)OC)C=O)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -23 | CELSIUS | 20 | MINUTE | To a solution of N,N,N'-trimethylethylenediamine (2.46 mL, 19.23 mmol) in 15 mL of 1,2-dimethoxyethane at -23° C. was added n-BuLi (9.22 mL, 19.23 mmol), and the solution was stirred at -23° C. for 20 min. The mixture was transferred using a double-tipped needle to a solution of 6-chloro-2-methoxy-3-pyridinecarboxaldeh... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | HI | COCCOC | -23 | 0.333333 | COc1nc(Cl)ccc1C=O.II>COCCOC>COc1nc(Cl)cc(I)c1C=O |
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