【结 构 式】 |
【分子编号】43918 【品名】1-(tert-butyl) 2-ethyl (2S)-4-(1-ethyl-1-hydroxypropyl)-5-oxo-1,2-pyrrolidinedicarboxylate 【CA登记号】 |
【 分 子 式 】C17H29NO6 【 分 子 量 】343.4204 【元素组成】C 59.46% H 8.51% N 4.08% O 27.95% |
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)Treatment of ethyl N-Boc-(S)-pyroglutamate (I) with lithium hexamethyldisilazide in THF at -78 C, followed by aldol condensation of the resulting lithium enolate with 3-pentanone (II) in the presence of boron trifluoride etherate, furnished adduct (III). Dehydration of the alcohol group of (III) to produce olefin (IV) was achieved by treatment of (III) with methanesulfonyl chloride and triethylamine. Hydrolysis of the ester and lactam groups of (IV) by means of LiOH afforded diacid (V). The N-Boc group of (V) was finally cleaved with HCl in EtOH.
【1】 Bleakman, D.; Ezquerra, J.; Baker, S.R.; et al.; 4-Alkylidenyl glutamic acids, potent and selective GluR5 agonists. Bioorg Med Chem Lett 2000, 10, 16, 1807. |
【2】 Rubio Esteban, A.; Pedregal Tercero, C. (Lilly SA); Glutamic acid derivs. and pharmaceutical compsns. for the treatment of central nervous system disorders. EP 0867430; ES 2133095; JP 1998279542 . |
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) | 43914 | 1-(tert-butyl) 2-ethyl (2S)-5-oxo-1,2-pyrrolidinedicarboxylate | 144978-35-8 | C12H19NO5 | 详情 | 详情 |
(II) | 32415 | Propione; Dimethylacetone; Diethyl ketone; 3-Pentanone | 96-22-0 | C5H10O | 详情 | 详情 |
(III) | 43918 | 1-(tert-butyl) 2-ethyl (2S)-4-(1-ethyl-1-hydroxypropyl)-5-oxo-1,2-pyrrolidinedicarboxylate | C17H29NO6 | 详情 | 详情 | |
(IV) | 43919 | 1-(tert-butyl) 2-ethyl (2S)-4-(1-ethylpropylidene)-5-oxo-1,2-pyrrolidinedicarboxylate | C17H27NO5 | 详情 | 详情 | |
(V) | 43920 | (2S)-2-[(tert-butoxycarbonyl)amino]-4-(1-ethylpropylidene)pentanedioic acid | C15H25NO6 | 详情 | 详情 |
Extended Information