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【结 构 式】 
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【分子编号】30780 【品名】methyl (2S)-1-(2-methoxy-2-oxoacetyl)-2-pyrrolidinecarboxylate 【CA登记号】 |
【 分 子 式 】C9H13NO5 【 分 子 量 】215.20596 【元素组成】C 50.23% H 6.09% N 6.51% O 37.17% |
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：(III)Acylation of L-proline methyl ester (I) with methoxalyl chloride (II) afforded oxamate (III), which was condensed with 1,1-dimethylpropyl magnesium chloride to produce ketoamide (IV). Hydrolysis of the methyl ester of (IV) with LiOH gave carboxylic acid (V). This was finally coupled with 3,3-diphenylpropyl mercaptan (VI) using DCC and dimethylaminopyridine to give the title thioether.
| 【1】 Limburg, D.C.; et al.; Synthesis of thioester FKBP12 ligands and evaluation of their in vitro and in vivo nerve regenerative effects. 217th ACS Natl Meet (March 21 1999, Anaheim) 1999, Abst MEDI 237. |
| 【2】 Hamilton, G.S.; Li, J.-H. (Guilford Pharmaceuticals Inc.); Heterocyclic thioesters and ketones. EP 0934263; US 5786378; US 5990131; WO 9813343 . |
| 【3】 Hamilton, G.S.; Steiner, J.P. (Guilford Pharmaceuticals Inc.); Hair growth compsns. and uses. WO 9855090 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 29552 | methyl (2S)-2-pyrrolidinecarboxylate | 2133-40-6 | C6H11NO2 | 详情 | 详情 |
| (II) | 26971 | 2-methoxy-2-oxoacetyl chloride | 5781-53-3 | C3H3ClO3 | 详情 | 详情 |
| (III) | 30780 | methyl (2S)-1-(2-methoxy-2-oxoacetyl)-2-pyrrolidinecarboxylate | C9H13NO5 | 详情 | 详情 | |
| (IV) | 30781 | methyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl)-2-pyrrolidinecarboxylate | C13H21NO4 | 详情 | 详情 | |
| (V) | 30782 | (2S)-1-(3,3-dimethyl-2-oxopentanoyl)-2-pyrrolidinecarboxylic acid | C12H19NO4 | 详情 | 详情 | |
| (VI) | 30783 | 3,3-diphenyl-1-propanethiol; 3,3-diphenylpropylhydrosulfide | C15H16S | 详情 | 详情 |
Extended Information