Title:
METHOD FOR PRODUCING 1-AMINO-1-ALKOXYCARBONYL-2-VINYLCYCLOPROPANE
Document Type and Number:
WIPO Patent Application WO/2011/102388
Kind Code:
A1
Abstract:
Provided is a novel method for producing (1R,2S)/(1S,2R)-1-amino-1-alkoxycarbonyl-2-vinylcyclopropane which is useful as an intermediate for synthesizing a therapeutic agent for hepatitis C, and also provided is a novel method for producing an intermediate for synthesizing (1R,2S)/(1S,2R)-1-amino-1-alkoxycarbonyl-2-vinylcyclopropane. According to the methods, when a trans-2-butene derivative having a leaving group at each of the 1- and 4-positions is reacted with a malonic acid ester in the presence of a base, a specific amount of an alkali metal alkoxide or an alkali metal hydride is used as the base, and further a specific amount of a malonic acid ester is used to produce a cyclopropane diester, and further, chiral or achiral 1-amino-1-alkoxycarbonyl-2-vinylcyclopropane and a salt thereof are synthesized using the cyclopropane diester.
Inventors:
ASUMA YUUKI (JP)
SUZUKI TATSUYA (JP)
TAKEHARA JUN (JP)
HIDAKA TSUGIHIKO (JP)
ASADA KUNIKO (JP)
MIYAKE RYOMA (JP)
DEKISHIMA YASUMASA (JP)
KAWABATA HIROSHI (JP)
SUZUKI TATSUYA (JP)
TAKEHARA JUN (JP)
HIDAKA TSUGIHIKO (JP)
ASADA KUNIKO (JP)
MIYAKE RYOMA (JP)
DEKISHIMA YASUMASA (JP)
KAWABATA HIROSHI (JP)
Application Number:
PCT/JP2011/053285
Publication Date:
August 25, 2011
Filing Date:
February 16, 2011
Export Citation:
Assignee:
API CORP (JP)
ASUMA YUUKI (JP)
SUZUKI TATSUYA (JP)
TAKEHARA JUN (JP)
HIDAKA TSUGIHIKO (JP)
ASADA KUNIKO (JP)
MIYAKE RYOMA (JP)
DEKISHIMA YASUMASA (JP)
KAWABATA HIROSHI (JP)
ASUMA YUUKI (JP)
SUZUKI TATSUYA (JP)
TAKEHARA JUN (JP)
HIDAKA TSUGIHIKO (JP)
ASADA KUNIKO (JP)
MIYAKE RYOMA (JP)
DEKISHIMA YASUMASA (JP)
KAWABATA HIROSHI (JP)
International Classes:
C07C67/343; C07C67/313; C07C69/743; C07C227/04; C07C227/32; C07C229/48; C12N15/09; C12P7/62; C07B53/00; C07B57/00; C07B61/00
Domestic Patent References:
WO2000064490A1 | 2000-11-02 | |||
WO2010041739A1 | 2010-04-15 |
Foreign References:
JPS63150249A | 1988-06-22 | |||
JPH01268634A | 1989-10-26 | |||
US4328168A | 1982-05-04 | |||
JPS5645425A | 1981-04-25 | |||
JP2005072209A | 2005-03-17 | |||
JP2009525320A | 2009-07-09 | |||
JPS5645425A | 1981-04-25 | |||
US4252739A | 1981-02-24 | |||
JP2005034025A | 2005-02-10 |
Other References:
SYNTHETIC COMMUNICATIONS, vol. 24, no. 20, 1994, pages 2873 - 2876, XP008164894
JOURNAL OF MEDICINAL CHEMISTRY, vol. 47, no. 10, 2004, pages 2511 - 2522, XP008165354
ITO, KODAMA ET AL., KABUSHIKI KAISHA TOKYO KAGAKU DOJIN, no. 4, 6 April 1998 (1998-04-06), pages 965 - 968, XP008146794
THE CHEMICAL SOCIETY OF JAPAN, JIKKEN KAGAKU KOZA, vol. 27, no. 4, 5 May 1991 (1991-05-05), pages 418 - 426, XP008166578
STEVEN D. R. CHRISTIE ET AL., CHEM. COMMUN., 2004, pages 2474 - 2475
KATSUHIKO MIURA ET AL., SYNLETT, 2006, pages 1883 - 1886
KATSUHIKO MIURA ET AL., J. ORG. CHEM., vol. 69, 2004, pages 2427 - 2430
GLENN S. SKINNER ET AL., J. AM. CHEM. SOC., vol. 70, 1950, pages 1648 - 1649
FREDERIC DOLLE ET AL., BIOORG. MED. CHEM., vol. 14, 2006, pages 1115 - 1125
See also references of EP 2537825A4
JOURNAL OF MEDICINAL CHEMISTRY, vol. 47, no. 10, 2004, pages 2511 - 2522, XP008165354
ITO, KODAMA ET AL., KABUSHIKI KAISHA TOKYO KAGAKU DOJIN, no. 4, 6 April 1998 (1998-04-06), pages 965 - 968, XP008146794
THE CHEMICAL SOCIETY OF JAPAN, JIKKEN KAGAKU KOZA, vol. 27, no. 4, 5 May 1991 (1991-05-05), pages 418 - 426, XP008166578
STEVEN D. R. CHRISTIE ET AL., CHEM. COMMUN., 2004, pages 2474 - 2475
KATSUHIKO MIURA ET AL., SYNLETT, 2006, pages 1883 - 1886
KATSUHIKO MIURA ET AL., J. ORG. CHEM., vol. 69, 2004, pages 2427 - 2430
GLENN S. SKINNER ET AL., J. AM. CHEM. SOC., vol. 70, 1950, pages 1648 - 1649
FREDERIC DOLLE ET AL., BIOORG. MED. CHEM., vol. 14, 2006, pages 1115 - 1125
See also references of EP 2537825A4
Attorney, Agent or Firm:
SIKs & Co. (JP)
Patent business corporation patent firm Sykes (JP)
Patent business corporation patent firm Sykes (JP)
Download PDF:
Claims:
Previous Patent: METHOD FOR PRODUCING REDUCED PYRROLOQUINOLINE QUINONE
Next Patent: INTEGRATED ILLUMINATION APPARATUS AND METHOD OF MANUFACTURING SAME
Next Patent: INTEGRATED ILLUMINATION APPARATUS AND METHOD OF MANUFACTURING SAME