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【结 构 式】

【分子编号】43915

【品名】1-(tert-butyl) 2-ethyl (2S)-4-(1-hydroxycyclopentyl)-5-oxo-1,2-pyrrolidinedicarboxylate

【CA登记号】

【 分 子 式 】C17H27NO6

【 分 子 量 】341.40452

【元素组成】C 59.81% H 7.97% N 4.1% O 28.12%

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 cyclopentanone (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) 15113 cyclopentanone 120-92-3 C5H8O 详情 详情
(III) 43915 1-(tert-butyl) 2-ethyl (2S)-4-(1-hydroxycyclopentyl)-5-oxo-1,2-pyrrolidinedicarboxylate C17H27NO6 详情 详情
(IV) 43916 1-(tert-butyl) 2-ethyl (2S)-4-cyclopentylidene-5-oxo-1,2-pyrrolidinedicarboxylate C17H25NO5 详情 详情
(V) 43917 (2S)-2-[(tert-butoxycarbonyl)amino]-4-cyclopentylidenepentanedioic acid C15H23NO6 详情 详情
Extended Information