A practical synthesis of trifluorophenyl R-amino acid: The key precursor for the new anti-diabetic drug sitagliptin

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	A practical synthesis of trifluorophenyl R-amino acid: The key precursor for the new anti-diabetic drug sitagliptin
	Zeng Li Li 1; Ding Ying Jie 1; Zhang Gui Cheng 1; Song Hong Rui 2; Hu Wen Hui 1
	2009
发表期刊	CHINESE CHEMICAL LETTERS
ISSN	1001-8417
卷号	20 期号:12 页码:1397-1399
摘要	Sitagliptin is the first new anti-diabetic drug in DPP-IV inhibitor class. The general synthesis of sitagliptin is by coupling of the beta-amino acid fragment with the heterocycle fragment. Though the specific beta-amino acid can be easily made from the corresponding R-amino acid by Arndt-Eistert homologation, the optically pure precursor R-amino acid is difficult to prepare. We herein reported a practical protocol to make the trifluorophenyl substituted R-amino acid 4 in >99.9% ee and 40.3% yield by the enzymatic resolution employing enantioselective hydrolysis and a general separation procedure. This protocol requires only cheap starting materials and friendly reaction condition. The procedure not only allows people to prepare the drug substance, but also provides an alternative method for prepareing the rare a-amino acid and the subsequent beta-amino acid. (C) 2009 Wen Hui Hu. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
关键词	PEPTIDASE-IV INHIBITORS GENERATION POTENT Sitagliptin beta-Amino acid DPP-IV inhibitor Practical synthesis
收录类别	CSCD
语种	英语
资助项目	[Guangdong Province]
CSCD记录号	CSCD:3778155
引用统计
文献类型	期刊论文
条目标识符	http://ir.imr.ac.cn/handle/321006/156573
专题	中国科学院金属研究所
作者单位	1.中国科学院 2.中国科学院金属研究所
推荐引用方式 GB/T 7714	Zeng Li Li,Ding Ying Jie,Zhang Gui Cheng,et al. A practical synthesis of trifluorophenyl R-amino acid: The key precursor for the new anti-diabetic drug sitagliptin[J]. CHINESE CHEMICAL LETTERS,2009,20(12):1397-1399.
APA	Zeng Li Li,Ding Ying Jie,Zhang Gui Cheng,Song Hong Rui,&Hu Wen Hui.(2009).A practical synthesis of trifluorophenyl R-amino acid: The key precursor for the new anti-diabetic drug sitagliptin.CHINESE CHEMICAL LETTERS,20(12),1397-1399.
MLA	Zeng Li Li,et al."A practical synthesis of trifluorophenyl R-amino acid: The key precursor for the new anti-diabetic drug sitagliptin".CHINESE CHEMICAL LETTERS 20.12(2009):1397-1399.