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【结 构 式】 
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【分子编号】65434 【品名】(1S,3aR,6aS)-2-[(2S)-2-[[(2S)-2-Cyclohexyl-2-[(2-pyrazinylcarbonyl)amino]acetyl]amino]-3,3-dimethyl-1-oxobutyl]octahydrocyclopenta[c]pyrrole-1-carboxylic acid tert-butyl ester 【CA登记号】926276-19-9 |
【 分 子 式 】C31H47N5O5 【 分 子 量 】569.74488 【元素组成】C 65.35% H 8.31% N 12.29% O 14.04% |
合成路线1
该中间体在本合成路线中的序号：(XX)An alternative route to the precursor N-acyl tripeptide (VIII) consists of coupling of N-Cbz-L-tert-leucine (XIII) with the bicyclic amino ester (XIV) to afford the protected dipeptide (XV), from which the N-Cbz group is removed by catalytic hydrogenolysis over Pearlman’s catalyst, yielding (XVI). The dipeptide ester (XVI) is then coupled with N-Cbz-L-cyclohexylglycine (XVII) to give (XVIII), which is further deprotected by catalytic hydrogenolysis to afford the tripeptide ester (XIX). After acylation of (XIX) with pyrazinecarboxylic acid (III) employing CDI, the resulting N-acyl tripeptide tert-butyl ester (XX) is treated with HCl in formic acid to provide the target intermediate (VIII) (3). Scheme 2.
| 【3】 Tanoury, G.J., Chen, M., Cochran, J.E. (Vertex Pharmaceuticals, Inc.). Processes and intermediates. WO 2007022459. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (III) | 37256 | 2-pyrazinecarboxylic acid; Pyrazinoic acid | 98-97-5 | C5H4N2O2 | 详情 | 详情 |
| (VIII) | 65423 | (1S,3aR,6aS)-(2S)-2-Cyclohexyl-N-(pyrazinylcarbonyl)glycyl-3-methyl-L-valyloctahydrocyclopenta[c]pyrrole-1-carboxylic acid | 402958-98-9 | C27H39N5O5 | 详情 | 详情 |
| (XIII) | 65427 | Cbz-L-tert-Leucine; (S)-N-Cbz-2-amino-3,3-dimethyl-butyric acid | 62965-10-0 | C14H19NO4 | 详情 | 详情 |
| (XIV) | 65428 | (1S,3aR,6aS)-Octahydrocyclopenta[c]pyrrole-1-carboxylic acid tert-butyl ester | 714194-68-0 | C12H21NO2 | 详情 | 详情 |
| (XV) | 65429 | (1S,3aR,6aS)-2-[(2S)-3,3-Dimethyl-1-oxo-2-[[(phenylmethoxy)carbonyl]amino]butyl]octahydrocyclopenta[c]pyrrole-1-carboxylic acid tert-butyl ester | 926276-15-5 | C26H38N2O5 | 详情 | 详情 |
| (XVI) | 65430 | (1S,3aR,6aS)-2-[(2S)-2-Amino-3,3-dimethyl-1-oxobutyl]octahydrocyclopenta[c]pyrrole-1-carboxylic acid tert-butyl ester | 926276-16-6 | C18H32N2O3 | 详情 | 详情 |
| (XVII) | 65431 | Cbz-Cyclohexyl-L-glycine; (S)-Cbz-Cyclohexylglycine; (S)-N-Cbz-Aminocyclohexylacetic acid | 69901-75-3 | C16H21NO4 | 详情 | 详情 |
| (XVIII) | 65432 | (1S,3aR,6aS)-2-[(2S)-2-[[(2S)-2-Cyclohexyl-2-[[(phenylmethoxy)carbonyl]amino]acetyl]amino]-3,3-dimethyl-1-oxobutyl]octahydrocyclopenta[c]pyrrole-1-carboxylic acid tert-butyl ester | 926276-17-7 | C34H51N3O6 | 详情 | 详情 |
| (XIX) | 65433 | (1S,3aR,6aS)-2-[(2S)-2-[[(2S)-2-Amino-2-cyclohexylacetyl]amino]-3,3-dimethyl-1-oxobutyl]octahydrocyclopenta[c]pyrrole-1-carboxylic acid tert-butyl ester | 926276-18-8 | C26H45N3O4 | 详情 | 详情 |
| (XX) | 65434 | (1S,3aR,6aS)-2-[(2S)-2-[[(2S)-2-Cyclohexyl-2-[(2-pyrazinylcarbonyl)amino]acetyl]amino]-3,3-dimethyl-1-oxobutyl]octahydrocyclopenta[c]pyrrole-1-carboxylic acid tert-butyl ester | 926276-19-9 | C31H47N5O5 | 详情 | 详情 |