Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof
Reexamination Certificate
2008-09-02
2008-09-02
Witherspoon, Sikarl A (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acids and salts thereof
C549S321000
Reexamination Certificate
active
10537293
ABSTRACT:
The invention concerns a method for preparing 4-hydroxyisoleucine diastereoisomers and enantiomers and derivatives thereof of general formula (I), characterized in that it consists in reducing an isoxazole derivative of formula (II) in conditions directly resulting in the derivatives of formula (I), or in obtaining at least a lactone of structure (III) in racemic form(s), or a enantiomerically enriched mixture, followed by opening, in basic conditions, in an aprotic or protic solvent, the desired lactone(s) and, optionally, separating the desired form. The invention is useful for preparing in particular (2S, 3R, 4S)-4-hydroxyisoleucine.
REFERENCES:
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patent: 5900237 (1999-05-01), Napper et al.
International Search Report for PCT/FR03/03542 dated Apr. 15, 2004.
Caplan et al..,Vinylogous Amide Analogues of Diaminopimelic Acid(DAP)as Inhibitors of Enzymes Involved in Bacterial Lysine Biosynthesis, Organic Letters, vol. 2, No. 24, 2000, pp. 3857-3860; XP-02247986.
Büchi et al.,Interchange of Functionality in Conjugated Carbonyl Compounds through Isoxazoles, Journal of the American Chemical Society, vol. 94, No. 26, Dec. 27, 1972; pp. 9128-9132; XP-002247987.
Becht Jean-Michel
Catala Cédric
De Lamo Marin Sandra
Mioskowski Charles
Wagner Alain
Centre National de la Recherche Scientifique (C.N.R.S.)
Nixon & Vanderhye P.C.
Universite Louis Pasteur
Witherspoon Sikarl A
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