Title:
METHOD FOR PRODUCING OPTICALLY ACTIVE CARBOXYLIC ACID ESTER
Document Type and Number:
WIPO Patent Application WO/2015/115650
Kind Code:
A1
Abstract:
Provided is a method for producing an optically active carboxylic acid ester at a high yield and with high enantioselectivity using dynamic kinetic resolution, said optically active carboxylic acid ester having an α-nitrogen substituent. This method for producing an optically active carboxylic acid ester includes a step in which racemic carboxylic acid represented by formula (a) and a specific alcohol or phenol derivative are reacted in a polar solvent having a dipole moment of at least 3.5 in the presence of an acid anhydride and an asymmetric catalyst, one enantiomer of the racemic carboxylic acid is selectively esterified, and the other enantiomer is racemized. In formula (a), Ra1 represents a nitrogen-containing heteroaromatic ring group bonded to an assymetric carbon via a nitrogen atom constituting a ring, and Ra2 is an organic group.
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Inventors:
SHIINA ISAMU (JP)
Application Number:
PCT/JP2015/052882
Publication Date:
August 06, 2015
Filing Date:
February 02, 2015
Export Citation:
Assignee:
UNIV TOKYO SCIENCE FOUNDATION (JP)
International Classes:
C07B53/00; C07D207/327; C07B55/00; C07D207/27; C07D207/333; C07D207/416; C07D209/08; C07D209/12; C07D209/34; C07D209/38; C07D209/48; C07D209/86; C07D235/06; C07D263/58; C07D403/06; C07B61/00; C07C269/06; C07C271/22; C07D471/04; C07D513/04
Domestic Patent References:
| WO2012169575A1 | 2012-12-13 | |||
| WO2009113428A1 | 2009-09-17 | |||
| WO2008140074A1 | 2008-11-20 | |||
| WO2009113428A1 | 2009-09-17 | |||
| WO2012169575A1 | 2012-12-13 |
Other References:
YANG,X. ET AL.: "Kinetic Resolution of alpha- Substituted Alkanoic Acids Promoted by Homobenzotetramisole", CHEMISTRY - A EUROPEAN JOURNAL, vol. 17, no. 40, 2011, pages 11296 - 11304, XP055163057
KEN'YA NAKATA ET AL.: "Racemic-2-Amino-2-Aryl Sakusan-rui no Seiteki Oyobi Doteki Sokudoron Kogaku Bunkatsu Hanno no Kaihatsu", CSJ: THE CHEMICAL SOCIETY OF JAPAN DAI 93 SHUNKI NENKAI (2013) KOEN YOKOSHU IV, 8 March 2013 (2013-03-08), pages 1371
TAKAYOSHI NAKAHARA ET AL.: "Racemic Amino San Hogotai no Doteki Sokudoron Kogaku Bunkatsu ni yoru Kogaku Kassei Amino San no Gosei", DAI 106 KAI SYMPOSIUM ON ORGANIC SYSTHESIS, 27 October 2014 (2014-10-27), JAPAN YOSHISHU, pages 74 - 75
ATSUSHI TENGEJI ET AL.: "Racemic Amino San Hogotai no Doteki Sokudoron-teki Kogaku Bunkatsu ni yoru Kogaku Kassei Amino San no Gosei", CSJ: THE CHEMICAL SOCIETY OF JAPAN DAI 94 SHUNKI NENKAI (2014) KOEN YOKOSHU IV, 12 March 2014 (2014-03-12), pages 1358
K. KASHIMA ET AL., J. CHEM. RES. MINIPRINT, 1988, pages 601 - 645
K. KASHIMA ET AL., J. CHEM. SOC. PERKIN TRANS., vol. 1, 1989, pages 1041 - 1046
X. YANG; V. B. BIRMAN, ANGEW. CHEM. INT. ED., vol. 50, 2011, pages 5553 - 5555
KEN'YA NAKATA ET AL.: "Racemic-2-Amino-2-Aryl Sakusan-rui no Seiteki Oyobi Doteki Sokudoron Kogaku Bunkatsu Hanno no Kaihatsu", CSJ: THE CHEMICAL SOCIETY OF JAPAN DAI 93 SHUNKI NENKAI (2013) KOEN YOKOSHU IV, 8 March 2013 (2013-03-08), pages 1371
TAKAYOSHI NAKAHARA ET AL.: "Racemic Amino San Hogotai no Doteki Sokudoron Kogaku Bunkatsu ni yoru Kogaku Kassei Amino San no Gosei", DAI 106 KAI SYMPOSIUM ON ORGANIC SYSTHESIS, 27 October 2014 (2014-10-27), JAPAN YOSHISHU, pages 74 - 75
ATSUSHI TENGEJI ET AL.: "Racemic Amino San Hogotai no Doteki Sokudoron-teki Kogaku Bunkatsu ni yoru Kogaku Kassei Amino San no Gosei", CSJ: THE CHEMICAL SOCIETY OF JAPAN DAI 94 SHUNKI NENKAI (2014) KOEN YOKOSHU IV, 12 March 2014 (2014-03-12), pages 1358
K. KASHIMA ET AL., J. CHEM. RES. MINIPRINT, 1988, pages 601 - 645
K. KASHIMA ET AL., J. CHEM. SOC. PERKIN TRANS., vol. 1, 1989, pages 1041 - 1046
X. YANG; V. B. BIRMAN, ANGEW. CHEM. INT. ED., vol. 50, 2011, pages 5553 - 5555
Attorney, Agent or Firm:
SHOBAYASHI, Masayuki (JP)
Right wood Masayuki (JP)
Right wood Masayuki (JP)
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