Title:
PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE FLUOROPROLINE DERIVATIVE
Document Type and Number:
WIPO Patent Application WO/2006/103986
Kind Code:
A1
Abstract:
A process for producing an optically active fluoroproline derivative represented by the general formula (2) by fluorinating an optically active hydroxyproline derivative represented by the general formula (1). The process comprises adding N-(2-chloro-1,1,2-trifluoroethyl) diethylamine or N-(1,1,2,3,3,3-hexafluoropropyl) diethylamine which is inexpensive and easy to handle to an aprotic nonpolar organic solvent at a temperature of 10&ring C or lower and then fluorinating the compound at a temperature ranging from 10 to 50&ring C. This process enables to produce an optically active fluoroproline derivative represented by the general formula (2) in which the configuration at position-4 of a compound represented by the general formula (1) is inverted, in a high purity with reduced by-product production. (1) (2) wherein R1 represents a substituted or unsubstituted alkyl or aryl group; R2 represents a substituted or unsubstituted alkyl, aryl, alkylcarbonyl, alkoxycarbonyl, arylcarbonyl or aryloxycarbonyl group; and an asterisk (*) denotes an asymmetric carbon.
Inventors:
KONDO NORIHISA (JP)
WATANABE AKIO (JP)
KANEZAKI HIROKI (JP)
KAWADA KOSUKE (JP)
WATANABE AKIO (JP)
KANEZAKI HIROKI (JP)
KAWADA KOSUKE (JP)
Application Number:
PCT/JP2006/305674
Publication Date:
October 05, 2006
Filing Date:
March 22, 2006
Export Citation:
Assignee:
TOSOH F TECH INC (JP)
KONDO NORIHISA (JP)
WATANABE AKIO (JP)
KANEZAKI HIROKI (JP)
KAWADA KOSUKE (JP)
KONDO NORIHISA (JP)
WATANABE AKIO (JP)
KANEZAKI HIROKI (JP)
KAWADA KOSUKE (JP)
International Classes:
C07D207/16; C07B53/00
Domestic Patent References:
| WO2005016880A1 | 2005-02-24 | |||
| WO2005021534A1 | 2005-03-10 |
Foreign References:
| JPH09241190A | 1997-09-16 | |||
| JPS63185979A | 1988-08-01 | |||
| JPS6239546A | 1987-02-20 | |||
| JPS62178566A | 1987-08-05 |
Other References:
DEMANGE L.: "Practical synthesis of Boc and Fmoc protected 4-fluoro and 4-difluoroprolines from trans-4-hydroxyproline", TETRAHEDRON LETTERS, vol. 39, no. 10, 1998, pages 1169 - 1172, XP004109146
HUDLICKY M.: "Stereospecific syntheses of all four stereoisomers of 4-fluoroglutamic acid", JOURNAL OF FLUORINE CHEMISTRY, vol. 60, no. 2-3, 1993, pages 193 - 210, XP003002211
HUDLICKY M.: "New stereospecific syntheses and x-ray diffraction structures of (-)-D-- and (+)-L--4-fluoroglutamic acid", TETRAHEDRON LETTERS, vol. 31, no. 51, 1990, pages 7403 - 7406, XP003002212
TAKAOKA A.: "F-Propene-Dialkylamine Reaction Products as Fluorinating Agents", BUL. CHEM. SOC. JPN., vol. 52, no. 11, 1979, pages 3377 - 3380, XP002971347
HUDLICKY M.: "Stereospecific syntheses of all four stereoisomers of 4-fluoroglutamic acid", JOURNAL OF FLUORINE CHEMISTRY, vol. 60, no. 2-3, 1993, pages 193 - 210, XP003002211
HUDLICKY M.: "New stereospecific syntheses and x-ray diffraction structures of (-)-D-- and (+)-L--4-fluoroglutamic acid", TETRAHEDRON LETTERS, vol. 31, no. 51, 1990, pages 7403 - 7406, XP003002212
TAKAOKA A.: "F-Propene-Dialkylamine Reaction Products as Fluorinating Agents", BUL. CHEM. SOC. JPN., vol. 52, no. 11, 1979, pages 3377 - 3380, XP002971347
Attorney, Agent or Firm:
Kishida, Masayuki (2-3 Marunouchi 2-chom, Chiyoda-ku Tokyo, JP)
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