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【结 构 式】 
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【分子编号】56075 【品名】(2S,4R)-4-hydroxy-N,N-dimethyl-2-pyrrolidinecarboxamide 【CA登记号】 |
【 分 子 式 】C7H14N2O2 【 分 子 量 】158.20044 【元素组成】C 53.15% H 8.92% N 17.71% O 20.23% |
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：(VII)Condensation of N-Boc-4-hydroxyproline (V) with dimethylamine using BOP as the coupling reagent furnished amide (VI). The N-Boc protecting group of (VI) was then removed under acidic conditions to yield prolinaminde (VII). Alkylation of (VII) with the chloro oxindole (IV) produced the N-indolyl proline derivative (VIII) as a mixture of diastereoisomers, separable by column chromatography. Finally, indole N acylation in (VIII) by means of 2,4-dimethoxybenzenesulfonyl chloride (IX) in the presence of NaH furnished the target sulfonamide.
| 【1】 Wagnon, J.; Tonnerre, B.; Roux, R.; Serradeil-Le Gal, C. (Sanofi-Synthelabo); Novel 1,3-dihydro-2H-indol-2-one derivs., preparation method and pharmaceutical compsns. containing them. EP 1255751; FR 2804114; WO 0155130 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IV) | 56073 | 3,5-dichloro-3-(2-methoxyphenyl)-1,3-dihydro-2H-indol-2-one | C15H11Cl2NO2 | 详情 | 详情 | |
| (V) | 16094 | (2S,4R)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid;1-(tert-butoxycarbonyl)-4®-hydroxy-L-proline;(2S,4R)-1-(tert-butoxycarbonyl)-4-hydroxytetrahydro-1H-pyrrole-2-carboxylic acid | 16094 | C10H17NO5 | 详情 | 详情 |
| (VI) | 56074 | tert-butyl (2S,4R)-2-[(dimethylamino)carbonyl]-4-hydroxy-1-pyrrolidinecarboxylate | C12H22N2O4 | 详情 | 详情 | |
| (VII) | 56075 | (2S,4R)-4-hydroxy-N,N-dimethyl-2-pyrrolidinecarboxamide | C7H14N2O2 | 详情 | 详情 | |
| (VIII) | 56076 | (2S,4R)-1-[5-chloro-3-(2-methoxyphenyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-4-hydroxy-N,N-dimethyl-2-pyrrolidinecarboxamide | C22H24ClN3O4 | 详情 | 详情 | |
| (IX) | 56077 | 2,4-dimethoxybenzenesulfonyl chloride | C8H9ClO4S | 详情 | 详情 |
Extended Information