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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 (INC. 1000, Kamoshida-cho, Aoba-ku, Yokohama-sh, Kanagawa 02, 〒2278502, JP)
阿須間 夕紀 (〒02 神奈川県横浜市青葉区鴨志田町1000番地 株式会社三菱化学科学技術研究センター内 Kanagawa, 〒2278502, JP)
SUZUKI Tatsuya (INC. 1000, Kamoshida-cho, Aoba-ku, Yokohama-sh, Kanagawa 02, 〒2278502, JP)
鈴木 竜哉 (〒02 神奈川県横浜市青葉区鴨志田町1000番地 株式会社三菱化学科学技術研究センター内 Kanagawa, 〒2278502, JP)
TAKEHARA Jun (1000 Kamoshida-cho, Aoba-ku, Yokohama-sh, Kanagawa 02, 〒2278502, JP)
竹原 潤 (〒02 神奈川県横浜市青葉区鴨志田町1000番地 株式会社エーピーアイ コーポレーション内 Kanagawa, 〒2278502, JP)
HIDAKA Tsugihiko (1-1 Kurosakishiroishi, Yahatanishi-ku, Kitakyushu-sh, Fukuoka 04, 〒8060004, JP)
日高 次彦 (〒04 福岡県北九州市八幡西区黒崎城石1番1号 株式会社エーピーアイ コーポレーション内 Fukuoka, 〒8060004, JP)
Application Number:
JP2011/053285
Publication Date:
August 25, 2011
Filing Date:
February 16, 2011
Export Citation:
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Assignee:
API CORPORATION (4-9 Hiranomachi 2-chome, Chuo-ku Osaka-sh, Osaka 46, 〒5410046, JP)
株式会社エーピーアイ コーポレーション (〒46 大阪府大阪市中央区平野町二丁目4番9号 Osaka, 〒5410046, JP)
ASUMA Yuuki (INC. 1000, Kamoshida-cho, Aoba-ku, Yokohama-sh, Kanagawa 02, 〒2278502, JP)
阿須間 夕紀 (〒02 神奈川県横浜市青葉区鴨志田町1000番地 株式会社三菱化学科学技術研究センター内 Kanagawa, 〒2278502, JP)
SUZUKI Tatsuya (INC. 1000, Kamoshida-cho, Aoba-ku, Yokohama-sh, Kanagawa 02, 〒2278502, JP)
鈴木 竜哉 (〒02 神奈川県横浜市青葉区鴨志田町1000番地 株式会社三菱化学科学技術研究センター内 Kanagawa, 〒2278502, JP)
TAKEHARA Jun (1000 Kamoshida-cho, Aoba-ku, Yokohama-sh, Kanagawa 02, 〒2278502, JP)
竹原 潤 (〒02 神奈川県横浜市青葉区鴨志田町1000番地 株式会社エーピーアイ コーポレーション内 Kanagawa, 〒2278502, JP)
HIDAKA Tsugihiko (1-1 Kurosakishiroishi, Yahatanishi-ku, Kitakyushu-sh, Fukuoka 04, 〒8060004, 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:
WO2000064490A12000-11-02
WO2010041739A12010-04-15
Foreign References:
JPS63150249A1988-06-22
JPH01268634A1989-10-26
US4328168A1982-05-04
JPS5645425A1981-04-25
JP2005072209A2005-03-17
JP2009525320A2009-07-09
JPS5645425A1981-04-25
US4252739A1981-02-24
JP2005034025A2005-02-10
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
See also references of EP 2537825A4
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
Attorney, Agent or Firm:
SIKs & Co. (8th Floor, Kyobashi-Nisshoku Bldg. 8-7, Kyobashi 1-chome, Chuo-k, Tokyo 31, 〒1040031, JP)
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Claims: