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Title:
PROCESS FOR PREPARATION OF OPTICALLY ACTIVE ETHYL 1-AMINO-2-ETHENYLCYCLOPROPANECARBOXYLATE
Document Type and Number:
WIPO Patent Application WO/2011/024691
Kind Code:
A1
Abstract:
A process for the preparation of optically active ethyl 1-amino-2-ethenylcyclopropanecarboxylate represented by formula (3), an enantiomer thereof, or acid addition salts of the same, which comprises a step of reacting a mixture containing the (1R, 2S) and (1S, 2R) isomers of ethyl 1-amino-2 -ethenylcyclopropanecarboxylate represented by formula (1) with an optically active tartranilic acid compound represented by general formula (2) to form a diastereomeric salt mixture, a step of separating one of the diastereomeric salts from the other thereof, and a step of treating each of the separated diastereomeric salts with either an acid or a base to decompose the diastereomeric salt. By this process, ethyl 1-amino-2 -ethenylcyclopropanecarboxylate with a high optical purity can be prepared efficiently.

Inventors:
YASUOKA, Junichi (2-25-1-107, Nishiokamoto Higashinada-ku, Kobe-sh, Hyogo 73, 〒6580073, JP)
安岡順一 (〒73 兵庫県神戸市東灘区西岡本2-25-1-107 Hyogo, 〒6580073, JP)
AIKAWA, Toshiaki (8-7-20-205, Hon-machi Toyonaka-sh, Osaka 21, 〒5600021, JP)
Application Number:
JP2010/063950
Publication Date:
March 03, 2011
Filing Date:
August 12, 2010
Export Citation:
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Assignee:
SUMITOMO CHEMICAL COMPANY, LIMITED (27-1, Shinkawa 2-chome Chuo-k, Tokyo 60, 〒1048260, JP)
住友化学株式会社 (〒60 東京都中央区新川二丁目27番1号 Tokyo, 〒1048260, JP)
YASUOKA, Junichi (2-25-1-107, Nishiokamoto Higashinada-ku, Kobe-sh, Hyogo 73, 〒6580073, JP)
安岡順一 (〒73 兵庫県神戸市東灘区西岡本2-25-1-107 Hyogo, 〒6580073, JP)
International Classes:
C07C227/34; C07B57/00; C07C229/48; C07C235/16
Foreign References:
JP2002522557A2002-07-23
JP2001089431A2001-04-03
JPH10218847A1998-08-18
JP2001097933A2001-04-10
JP2004051604A2004-02-19
JP2001131148A2001-05-15
JP2006282605A2006-10-19
JP2006282606A2006-10-19
JP2006282607A2006-10-19
Other References:
PIERRE L. B. ET AL.: "Synthesis of (1R, 2S)-1-Amino-2-vinylcyclopropanecarboxylic Acid Vinyl-ACCA) Derivatives: Key Intermediates for the Preparation of Inhibitors of the Hepatitis C Virus NS3 Protease", J. ORG. CHEM., vol. 70, no. 15, 2005, pages 5869 - 5879, XP002686607, DOI: doi:10.1021/JO050468Q
Attorney, Agent or Firm:
NAKAYAMA, Tohru et al. (Limited 5-33, Kitahama 4-chome, Chuo-ku, Osaka-sh, Osaka 50, 〒5418550, JP)
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