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 (JP)
YAMAZAKI TAKAKO (JP)
ISHII SHOKO (JP)
MIMURA SHUNSUKE (JP)
FUSHIMI MASANORI (JP)
OKAMOTO RYUICHI (JP)
KOBAYASHI HARUKI (JP)
YASUMOTO MANABU (JP)
YAMAZAKI TAKAKO (JP)
ISHII SHOKO (JP)
MIMURA SHUNSUKE (JP)
FUSHIMI MASANORI (JP)
OKAMOTO RYUICHI (JP)
KOBAYASHI HARUKI (JP)
YASUMOTO MANABU (JP)
Application Number:
PCT/JP2016/068748
Publication Date:
January 05, 2017
Filing Date:
June 24, 2016
Export Citation:
Assignee:
CENTRAL GLASS CO LTD (JP)
International Classes:
C07D327/10; C07C67/313; C07C67/343; C07C67/52; C07C69/74; C07B57/00
Foreign References:
JP2008230970A | 2008-10-02 | |||
JP2006328011A | 2006-12-07 | |||
US20110213176A1 | 2011-09-01 | |||
US20150175626A1 | 2015-06-25 | |||
US20110245529A1 | 2011-10-06 | |||
US20110201825A1 | 2011-08-18 |
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
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
Attorney, Agent or Firm:
KOBAYASHI, Hiromichi et al. (JP)
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