diethyl (3aS,6aS)-5-[bis(tert-butoxycarbonyl)amino]-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole-3,5-dicarboxylate -Drug Synthesis Database

【结构式】

【分子编号】64708

【品名】diethyl (3aS,6aS)-5-[bis(tert-butoxycarbonyl)amino]-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole-3,5-dicarboxylate

【CA登记号】

【分子式】C₂₂H₃₄N₂O₉

【分子量】470.52004

【元素组成】C 56.16% H 7.28% N 5.95% O 30.6%

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：(IV)

The mono-Boc protected amino cyclopentenecarboxylate (I) is converted to the di-Boc derivative (II) by means of di-tert-butyl dicarbonate and DMAP. Dipolar cycloaddition of the nitrile oxide generated from ethyl 2-chloro-2-(hydroxyimino)acetate (III) to cyclopentene (II) gives the cis-fused cyclopentaisoxazole (IV) as a diastereomeric mixture. After cleavage of the acidic Boc groups, the desired isomer (V) can be isolated by column chromatography. Finally, alkaline hydrolysis of the ethyl ester functions of (V) affords the target dicarboxylic acid.

参考文献中间体

合成目标

【1】 Conti, P.; De Amici, M.; Di Ventimiglia, S.J.; Stensbol, T.B.; Madsen, U.; Brauner-Osborne, H.; Russo, E.; De Sarro, G.; Bruno, G.; De Micheli, C.; Synthesis and anticonvulsant activity of novel bicyclic acidic amino acids. J Med Chem 2003, 46, 14, 3102.

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)	64706	ethyl 1-[(tert-butoxycarbonyl)amino]-3-cyclopentene-1-carboxylate		C₁₃H₂₁NO₄	详情	详情
(II)	64707	ethyl 1-[bis(tert-butoxycarbonyl)amino]-3-cyclopentene-1-carboxylate		C₁₈H₂₉NO₆	详情	详情
(III)	30424	2-ethoxy-N-hydroxy-2-oxoethanimidoyl chloride	14337-43-0	C₄H₆ClNO₃	详情	详情
(IV)	64708	diethyl (3aS,6aS)-5-[bis(tert-butoxycarbonyl)amino]-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole-3,5-dicarboxylate		C₂₂H₃₄N₂O₉	详情	详情
(V)	64709	diethyl (3aS,5R,6aS)-5-amino-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole-3,5-dicarboxylate		C₁₂H₁₈N₂O₅	详情	详情

Extended Information