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Chemical Synthesis of the ODM-201's Diastereomers through an Efficient Intramolecular 1,3-Dipolar Cycloaddition.

Authors
  • Pan, Tingting1
  • Xia, Chunguang2
  • Jiang, Huijuan1
  • Zhang, Zhongtang1
  • Zhu, Xueyan1
  • Yang, Yulei1
  • 1 State Key Lab of New Drug & Pharmaceutical Process, State Institute of Pharmaceutical Industry.
  • 2 Chia Tai Tianqing Pharmaceutical Group Co., Ltd.
Type
Published Article
Journal
Chemical and Pharmaceutical Bulletin
Publisher
Pharmaceutical Society of Japan
Publication Date
Jun 01, 2017
Volume
65
Issue
6
Pages
582–585
Identifiers
DOI: 10.1248/cpb.c17-00176
PMID: 28381698
Source
Medline
Keywords
License
Unknown

Abstract

An efficient synthesis of ODM-201's diastereomers has been developed from (R)-methyl 3-hydroxybutanoate or (S)-methyl 3-hydroxybutanoate, respectively, with high overall yield and excellent diastereomeric purity. The key step in this synthesis is the preparation of the key intermediate (R)-5-(1-((tert-butyldimethylsilyl)oxy)ethyl)-1H-pyrazole-3-carboxylic acid or (S)-5-(1-((tert-butyldimethylsilyl)oxy)ethyl)-1H-pyrazole-3-carboxylic acid through intramolecular 1,3-dipolar cycloaddition of the vinyl diazo carbonyl compounds.

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