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【结 构 式】 
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【分子编号】38573 【品名】(2S,4S)-1-[(benzyloxy)carbonyl]-4-hydroxy-4-phenyl-2-pyrrolidinecarboxylic acid 【CA登记号】 |
【 分 子 式 】C19H19NO5 【 分 子 量 】341.3636 【元素组成】C 66.85% H 5.61% N 4.1% O 23.43% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：(XXX)The Grignard condensation of N-(benzyloxycarbonyl)-4-oxo-L-proline (XXIX) with phenylmagnesium bromide gives the 4-hydroxy-4-phenylproline derivative (XXX), which is dehydrated with TFA yielding the dehydroproline (XXXI). The hydrogenation of (XXXI) with Li in liquid ammonia affords the previously reported trans-4-phenyl-L-proline (XIX), which is hydrogenated to the corresponding cyclohexyl derivative (XI) with H2 over PtO2.
| 【1】 Powell, J.R.; Cushman, D.W.; Krapcho, J.; Turk, C.; DeForrest, J.M.; Spitzmiller, E.R.; Karanewsky, D.S.; Duggan, M.; Rovnyak, G.; Schwartz, J.; et al.; Angiotensin-converting enzyme inhibitors. Mercaptan, carboxyalkyl dipeptide, and phosphinic acid inhibitors incorporating 4-substituted prolines. J Med Chem 1988, 31, 6, 1148. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XI) | 38567 | (2S,4S)-4-cyclohexyl-2-pyrrolidinecarboxylic acid | C11H19NO2 | 详情 | 详情 | |
| (XIX) | 38572 | (2S,4S)-4-phenyl-2-pyrrolidinecarboxylic acid | C11H13NO2 | 详情 | 详情 | |
| (XXIX) | 11357 | (2S)-1-[(Benzyloxy)carbonyl]-4-oxotetrahydro-1H-pyrrole-2-carboxylic acid | C13H13NO5 | 详情 | 详情 | |
| (XXX) | 38573 | (2S,4S)-1-[(benzyloxy)carbonyl]-4-hydroxy-4-phenyl-2-pyrrolidinecarboxylic acid | C19H19NO5 | 详情 | 详情 | |
| (XXXI) | 38574 | (2S)-1-[(benzyloxy)carbonyl]-4-phenyl-2,5-dihydro-1H-pyrrole-2-carboxylic acid | C19H17NO4 | 详情 | 详情 |
Extended Information