(2S)-2-[(tert-butoxycarbonyl)amino]-4-cyclopentylidenepentanedioic acid -Drug Synthesis Database

【结构式】

【分子编号】43917

【品名】(2S)-2-[(tert-butoxycarbonyl)amino]-4-cyclopentylidenepentanedioic acid

【CA登记号】

【分子式】C₁₅H₂₃NO₆

【分子量】313.35076

【元素组成】C 57.5% H 7.4% N 4.47% O 30.64%

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：(V)

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.

参考文献中间体

合成目标

【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