PROCESS FOR PREPARATION OF OPTICALLY ACTIVE ETHYL 1-AMINO-2-ETHENYLCYCLOPROPANECARBOXYLATE

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 (JP)
AIKAWA TOSHIAKI (JP)
IKEMOTO TETSUYA (JP)

Application Number:

PCT/JP2010/063950

Publication Date:

March 03, 2011

Filing Date:

August 12, 2010

Export Citation:

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Assignee:

SUMITOMO CHEMICAL CO (JP)
YASUOKA JUNICHI (JP)
AIKAWA TOSHIAKI (JP)
IKEMOTO TETSUYA (JP)

International Classes:

C07C227/34; C07B57/00; C07C229/48; C07C235/16

Foreign References:

JP2002522557A	2002-07-23
JP2001089431A	2001-04-03
JPH10218847A	1998-08-18
JP2001097933A	2001-04-10
JP2004051604A	2004-02-19
JP2001131148A	2001-05-15
JP2006282605A	2006-10-19
JP2006282606A	2006-10-19
JP2006282607A	2006-10-19

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. (JP)
Toru Nakayama (JP)

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