Title:
OPTICALLY ACTIVE 2-ALLYLCARBOXYLIC ACID DERIVATIVE AND PROCESS FOR PRODUCING THE SAME
Document Type and Number:
WIPO Patent Application WO/2004/092113
Kind Code:
A1
Abstract:
A process by which an optically active 2-allylcarboxylic acid derivative which is useful as an intermediate for medicines can be easily and industrially produced from a material available at low cost; and a 2-allylcarboxamide derivative which is a novel important intermediate therefor. An N-allylcarboxamide derivative is reacted with a base by diastereoselective rearrangement to obtain a 2-allylcarboxamide derivative. This derivative is converted to a carbamate and solvolyzed to obtain an optically active 2-allylcarboxylic ester. This ester is stereoselectively hydrolyzed with an enzyme to produce a 2-allylcarboxylic acid having a high optical purity. The 2-allylcarboxamide derivative compound is a novel intermediate in the production process.
Inventors:
OKURO KAZUMI (JP)
AMANO SUSUMU (JP)
KIZAKI NORIYUKI (JP)
TAKESUE TERUAKI (JP)
MITSUDA MASARU (JP)
ITO NORIYUKI (JP)
YASOHARA YOSHIHIKO (JP)
AMANO SUSUMU (JP)
KIZAKI NORIYUKI (JP)
TAKESUE TERUAKI (JP)
MITSUDA MASARU (JP)
ITO NORIYUKI (JP)
YASOHARA YOSHIHIKO (JP)
Application Number:
PCT/JP2004/005465
Publication Date:
October 28, 2004
Filing Date:
April 16, 2004
Export Citation:
Assignee:
KANEKA CORP (JP)
ONO PHARMACEUTICAL CO (JP)
OKURO KAZUMI (JP)
AMANO SUSUMU (JP)
KIZAKI NORIYUKI (JP)
TAKESUE TERUAKI (JP)
MITSUDA MASARU (JP)
ITO NORIYUKI (JP)
YASOHARA YOSHIHIKO (JP)
ONO PHARMACEUTICAL CO (JP)
OKURO KAZUMI (JP)
AMANO SUSUMU (JP)
KIZAKI NORIYUKI (JP)
TAKESUE TERUAKI (JP)
MITSUDA MASARU (JP)
ITO NORIYUKI (JP)
YASOHARA YOSHIHIKO (JP)
International Classes:
C07C51/00; C07C67/20; C07C233/05; C07C233/18; C07C271/64; C12P7/40; C12P41/00; (IPC1-7): C07C233/09; C07C57/03; C07C67/20; C07C69/533; C07C231/08; C07C231/20; C07C233/20; C07C269/02; C07C271/64; C12N9/16; C12P41/00
Foreign References:
| JPS5826847A | 1983-02-17 |
Other References:
PORTER N A, ET AL: "Control of dispersity and stereochemistry in freee radical telomerization: a radical addition, cyclization, chain transfer (ACT) strategy", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 116, no. 22, 1994, pages 10255 - 10266, XP002980588
JOENSSON S, ET AL: "Enantiomers of methyl substituted analogs of (z)-5-decenyl acetate as probes for the chirality and complementarity of its receptor in agrotis segetum: synthesis and structure-activity relationships", JOURNAL OF CHEMICAL ECOLOGY, vol. 19, no. 3, 1993, pages 459 - 484, XP002980589
KURTH M J, ET AL: "Asymmetric induction in the Claisen rearrangement of N-allylketene N,O-acetals", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 107, no. 2, 1985, pages 443 - 448, XP002980590
RAMA RAO A V, ET AL: "Studies on cyclodepsipeptides - Part I: a stereoselective synthesis of C12 polyketide unit (C1-C8) present in jaspamide and geodiamolide A-F", TETRAHEDRON LETTERS, vol. 34, no. 44, 1993, pages 7081 - 7084, XP002980591
HIROI K, ET AL: "Asymmetric induction reactions. II. stereohemical studies on asymmetric [2,3] sigmatropic rearrangements using chiral ketenimimes", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 33, no. 11, 1985, pages 4691 - 4700, XP002980592
See also references of EP 1650187A4
JOENSSON S, ET AL: "Enantiomers of methyl substituted analogs of (z)-5-decenyl acetate as probes for the chirality and complementarity of its receptor in agrotis segetum: synthesis and structure-activity relationships", JOURNAL OF CHEMICAL ECOLOGY, vol. 19, no. 3, 1993, pages 459 - 484, XP002980589
KURTH M J, ET AL: "Asymmetric induction in the Claisen rearrangement of N-allylketene N,O-acetals", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 107, no. 2, 1985, pages 443 - 448, XP002980590
RAMA RAO A V, ET AL: "Studies on cyclodepsipeptides - Part I: a stereoselective synthesis of C12 polyketide unit (C1-C8) present in jaspamide and geodiamolide A-F", TETRAHEDRON LETTERS, vol. 34, no. 44, 1993, pages 7081 - 7084, XP002980591
HIROI K, ET AL: "Asymmetric induction reactions. II. stereohemical studies on asymmetric [2,3] sigmatropic rearrangements using chiral ketenimimes", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 33, no. 11, 1985, pages 4691 - 4700, XP002980592
See also references of EP 1650187A4
Attorney, Agent or Firm:
Yasutomi, Yasuo (4-20 Nishinakajima 5-chome, Yodogawa-k, Osaka-shi Osaka 11, JP)
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