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Title:
METHOD FOR PRODUCING FLUORINE-CONTAINING CYCLOPROPANE CARBOXYLIC ACID COMPOUND
Document Type and Number:
WIPO Patent Application WO/2017/002712
Kind Code:
A1
Abstract:
The present invention provides an industrially practicable method for producing a fluorine-containing cyclopropane carboxylic acid compound that is useful as an intermediate for pharmaceuticals and agrochemicals. A fluorine-containing cyclopropane monoester is obtained by: producing a fluorine-containing cyclic sulfuric acid ester with use of a fluorine-containing diol compound and sulfuryl fluoride (a cyclic sulfuric acid esterification step); obtaining a fluorine-containing cyclopropane diester by reacting the thus-obtained fluorine-containing cyclic sulfuric acid ester and a malonic acid diester with each other (a cyclopropanation step); and hydrolyzing the thus-obtained fluorine-containing cyclopropane diester (a hydrolysis step). In addition, a fluorine-containing cyclopropane carboxylic acid compound such as a fluorine-containing cyclopropane monoester or a salt thereof having high chemical purity and high optical purity is able to be produced by forming a salt of an amine and a fluorine-containing cyclopropane monoester by mixing the thus-obtained fluorine-containing cyclopropane monoester and an amine and performing recrystallization purification (a recrystallization step).

Inventors:
KASHIWABA, Takashi (LIMITED 17-5, Nakadai 2-chome, Kawagoe-sh, Saitama 59, 〒3501159, JP)
YAMAZAKI, Takako (LIMITED 17-5, Nakadai 2-chome, Kawagoe-sh, Saitama 59, 〒3501159, JP)
ISHII, Shoko (LIMITED 17-5, Nakadai 2-chome, Kawagoe-sh, Saitama 59, 〒3501159, JP)
MIMURA, Shunsuke (LIMITED 17-5, Nakadai 2-chome, Kawagoe-sh, Saitama 59, 〒3501159, JP)
FUSHIMI, Masanori (LIMITED 17-5, Nakadai 2-chome, Kawagoe-sh, Saitama 59, 〒3501159, JP)
OKAMOTO, Ryuichi (LIMITED 17-5, Nakadai 2-chome, Kawagoe-sh, Saitama 59, 〒3501159, JP)
KOBAYASHI, Haruki (LIMITED 17-5, Nakadai 2-chome, Kawagoe-sh, Saitama 59, 〒3501159, JP)
YASUMOTO, Manabu (LIMITED 17-5, Nakadai 2-chome, Kawagoe-sh, Saitama 59, 〒3501159, JP)
Application Number:
JP2016/068748
Publication Date:
January 05, 2017
Filing Date:
June 24, 2016
Export Citation:
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Assignee:
CENTRAL GLASS COMPANY, LIMITED (5253, Oaza Okiube Ube-sh, Yamaguchi 01, 〒7550001, JP)
International Classes:
C07D327/10; C07C67/313; C07C67/343; C07C67/52; C07C69/74; C07B57/00
Foreign References:
JP2008230970A2008-10-02
JP2006328011A2006-12-07
US20110213176A12011-09-01
US20150175626A12015-06-25
US20110245529A12011-10-06
US20110201825A12011-08-18
Other References:
KARADEOLIAN, A. ET AL.: "Examination of Homo- [3+2]-Dipolar Cycloaddition: Mechanistic Insight into Regio and Diastereoselectivity", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 72, no. 26, 2007, pages 10251 - 10253, XP055342754
BURGESS, K. ET AL.: "Synthesis of a Valuable Cyclopropyl Chiron for Preparation of 2,3- Methanoamino Acids", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 58, no. 14, 1993, pages 3767 - 3768, XP002060010
See also references of EP 3315497A4
Attorney, Agent or Firm:
KOBAYASHI, Hiromichi et al. (Ekisaikai Bldg. 1-29, Akashi-cho, Chuo-k, Tokyo 44, 〒1040044, JP)
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