Synthesis of Methyl 2-(1-tert-Butoxycarbonylaminoethyl)thiazole-4-carboxylate

Chinese Journal of Organic Chemistry ›› 2004, Vol. 24 ›› Issue (5): 512-515. Previous Articles Next Articles

2-[1-(叔丁氧羰基氨基)乙基]噻唑-4-甲酸甲酯的合成

王晓季, 陈立功^*, 李阳, 孟祎

天津大学药物科学与技术学院天津 300072

收稿日期:2003-06-17 修回日期:2003-10-16 接受日期:2003-11-14 发布日期:2022-09-20

Synthesis of Methyl 2-(1-tert-Butoxycarbonylaminoethyl)thiazole-4-carboxylate

WANG, Xiao-Ji, CHEN, Li-Gong^*, LI, Yang, MENG, Yi

School of Pharmaceutical Technology & Science, Tianjin University, Tianjin 300072

Received:2003-06-17 Revised:2003-10-16 Accepted:2003-11-14 Published:2022-09-20
Contact: *E-mail: lgchen@tju.edu.cn

Abstract

Methyl 2-(1-tert-butoxycarbonylaminoethyl)thiazole-4-carboxylate, the chiral unit containing thiazole of a novel cyclic depsipeptide obyanamide which exhibited moderate cytotoxicity against KB andLoVo cells, was synthesized from (S)-serine and N-Boc-(S)-alanine in overall yield 21.4% through seven steps, including esterification, condensation, TBS protection, thionation, deprotection, cyclization and dehydrogenation. The ee value of the title chiral thiazole unit is up to 98%.

Key words: (S)-serine, N-Boc-(S)-alanine, thiazole

Cite this article

WANG, Xiao-Ji, CHEN, Li-Gong, LI, Yang, MENG, Yi. Synthesis of Methyl 2-(1-tert-Butoxycarbonylaminoethyl)thiazole-4-carboxylate[J]. Chinese Journal of Organic Chemistry, 2004, 24(5): 512-515.

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2-[1-(叔丁氧羰基氨基)乙基]噻唑-4-甲酸甲酯的合成

Synthesis of Methyl 2-(1-tert-Butoxycarbonylaminoethyl)thiazole-4-carboxylate

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