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A practical synthesis of trifluorophenyl R-amino acid: The key precursor for the new anti-diabetic drug sitagliptin
Zeng Li Li1; Ding Ying Jie1; Zhang Gui Cheng1; Song Hong Rui2; Hu Wen Hui1
2009
Source PublicationCHINESE CHEMICAL LETTERS
ISSN1001-8417
Volume20Issue:12Pages:1397-1399
AbstractSitagliptin 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.
KeywordPEPTIDASE-IV INHIBITORS GENERATION POTENT Sitagliptin beta-Amino acid DPP-IV inhibitor Practical synthesis
Indexed ByCSCD
Language英语
Funding Project[Guangdong Province]
CSCD IDCSCD:3778155
Citation statistics
Document Type期刊论文
Identifierhttp://ir.imr.ac.cn/handle/321006/156573
Collection中国科学院金属研究所
Affiliation1.中国科学院
2.中国科学院金属研究所
Recommended Citation
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.
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