Optically active 2-allylcarboxylic acid derivative and...

Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof

Reexamination Certificate

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C562S443000, C560S115000, C560S020000

Reexamination Certificate

active

10553394

ABSTRACT:
The present invention provides a process for producing an optically active 2-allylcarboxylic acid derivative, which is useful as a pharmaceutical intermediate, from readily available and inexpensive starting materials by the process which can be practiced on a commercial scale in a simple and easy manner, and certain 2-allylcarboxamide derivatives, which are novel and important intermediates in that process.An N-allylcarboxamide derivative undergoes rearrangement reaction diastereoselectively in the presence of a base to give a 2-allylcarboxamide derivative, the resulting derivative is subjected to a carbamation reaction and solvolysis to give an optically active 2-allylcarboxylic acid ester, and then the ester obtained is stereoselectively hydrolyzed using an enzyme to produce 2-allylcarboxylic acid having a high optical purity. In addition, the present invention provides a 2-allylcarboxamide derivative compound which is a novel intermediate in the process of the present invention.

REFERENCES:
patent: 6333415 (2001-12-01), Yamamoto
patent: 58-26847 (1983-02-01), None
patent: SHO-58-026847 (1983-02-01), None
patent: HEI-8-291106 (1996-11-01), None
patent: WO99/58513 (1999-11-01), None
Bock et al., European Journal of Biochemistry (1971), 23(2), abstract.
Ohtsuji, Kanazawa Daigaku Juzen Igakkai Zasshi (1996), 105(5), abstract.
Suh et al., Chemical Communications (2002), 10, abstract.
Baldwin et al., Biochemical Journal (1994), 301, abstract.
Tsunoda et al., “Asymmetric induction in aza-claisen rearrangement of carboxamide enolates. Effect of chiral auxillary on nitrogen”, Tetrahedron Letters, vol. 33, No. 12, pp. 1651-1654 (1992).
Ito et al., “A few new methods for asymmetric synthesis”, Pure & Applied chemistry, vol. 62, No. 7, p. 1405-1408 (1990).
Ned A. Porter, et al, “Control of Dispersity and Stereo Chemistry in Free Radical Telomerizations: A Radical Addition, Cylization, Chain Transfer(ACT) Strategy”, Journal of the American Chemical Society, vol. 116, No. 22, 1994, pp. 10255-10266 (compound 19a-d).
Stig Joensson, et al, “Enantiomers of Methyl-Substituted Analogs of (Z)-5-Decenyl Acetate as Probes for the Chirality and Complementarity of Its Receptor inAgrotis segetum: Synthesis and Structure-Activity Relationships”, Journal of Chemical Ecology, vol. 19, No. 3 1993, pp. 459-484 (Fig. 2).
Mark J. Kurth, 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, pp. 443-448 (compound 11r, 12s).
A.V. Rama Rao, et al, “Studies on Cyclo Depsipeptides-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, pp. 7081-7084 (compounds 7, 8).
Kunio Hiroi, et al, “Asymmetric Induction Reactions. II. Stereochemical Studies on Asymmetric [2, 3] Sigmatropic Rearrangements Using Chiral Ketenimines” Chemical & Pharmaceutical Bulletin, vol. 33, No. 11, 1985, pp. 4691-4700 (chart-2).
N. Porter, et al, Journal of the American Chemical Society, vol. 116, No. 22, 1994, pp. 10255-10266.
S. Jönsson, et al, Journal of Chemical Ecology, vol. 19, No. 3, 1993, pp. 459-484.
M. Kurth, et al, Journal of the American Chemical Society, vol. 107, No. 2, 1985, pp. 443-448.
A. Rao, et al, Tetrahedron Letters, vol. 34, No. 44, 1993, pp. 7081-7084.
K. Hirol, et al, Chemical & Pharmaceutical Bulletin, vol. 33, No. 11, 1985, pp. 4691-4700.

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