Process for the preparation of enantiomerically enriched...

Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...

Reexamination Certificate

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C554S162000, C554S163000, C554S170000

Reexamination Certificate

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06841691

ABSTRACT:
Method for the preparation of an enantiomerically enriched ester, in which a mixture of the enantiomers of the corresponding secondary alcohol is subjected, in the presence of an acyl donor, to an enantioselective conversion in the presence of a racemisation catalyst upon which the ester is formed and an acyl donor residue is obtained, and in which the acyl donor residue is irreversibly removed from the phase in which the enantioselective conversion takes place. Preferably the enantioselective conversion is carried out enzymatically and a transfer hydrogenation catalyst is used as racemisation catalyst.The secondary alcohol can be formed in situ from the corresponding ketone, in the presence of a hydrogen donor. It is also possible to use a mixture of the secondary alcohol and the corresponding ketone as substrate.Preferably the acyl donor is chosen so that the acyl donor residue is converted in situ into another compound and/or the acyl donor residue is removed via distillation under reduced pressure.The enantiomerically enriched esters obtained can subsequently be converted into the corresponding enantiomerically enriched alcohols, which are desirable intermediate products in the preparation of liquid crystals, agro chemicals or pharmaceuticals.

REFERENCES:
patent: 5726172 (1998-03-01), Sparks et al.
patent: 5750549 (1998-05-01), Caldwell et al.
patent: 5808056 (1998-09-01), Amato et al.
patent: 4237920 (1992-11-01), None
patent: 4329293 (1995-03-01), None
patent: 0321918 (1989-06-01), None
patent: 314003 (1991-08-01), None
patent: 248414 (1992-09-01), None
patent: 916637 (1999-05-01), None
patent: 360622 (1999-07-01), None
patent: 03236347 (1991-10-01), None
patent: 10245889 (1998-09-01), None
patent: 2000010068 (2000-01-01), None
patent: WO 8902425 (1989-03-01), None
patent: WO 9627615 (1996-09-01), None
patent: WO 9736864 (1997-10-01), None
patent: WO 9845268 (1998-10-01), None
patent: WO 9948530 (1999-09-01), None
Brodfuehrer, P.R. et al., “Asymmetric Synthesis of the Antiarrhythmia Agent d-Sotalol” Org. Process Res. Dec. 1(2):176-178 (1997).
Cohen, N. and Banner, B.L., “Synthesis of 2-Amino-5,6-dihydro-4H-1,3-thiazines and Related Compounds by Acid Catalyzed Cyclization of Allylic Isothiuonium Salts” J. Heterocycl. Chem. 14(5):717-23 (1977).
Fu, G.C., “From Planarity to Chirality” Chemical Innovation 3-5 (Jan. 2000).
Garrett, C.E. et al., “Nucleophilic Catalysis with π-Bound Nitrogen Heterocycles: Synthesis of the First Ruthenium Catalysts and Comparison of the Reactivity and the Enantioselectivity of Ruthenium and Iron Complexes” J.A. Chem Soc. 120:7479-7483 (1998).
Krämer, R. et al., “Chirale Halbsandwich-Komplexe von Cobalt (III), Rhodium(III), Iridium(III) und Ruthenium(II) Mit Alfa-Aminosäureamid-Glycinnitril- und Peptidester-Liganden” Chemische Berichte, Verlag Chemie GMBH. Weinheim, DE, 126(9):1969-1980 (1993).
Larsson, A. et al., “Enzymatic Resolution of Alcohols Coupled with Ruthenium-Catalyzed Racemization of the Substrate Alcohol” Angew. Chem. Int. Ed. Engl. 36(11):1211-1212 (1997).
Oguni, N. et al., “Enantioselective Addition of Diethylzinc to Arylaldehydes Catalyzed by Chiral Cobalt (II) and Palladium (II) Complexes” Chem. Lett. 6:841-2 (1983).
Palmer, M.J. and Wills, M., “Asymmetric Transfer Hydrogenation of C═and C═N Bonds” Tetrahedron: Asymmetry 10:2045-2061 (1999).
Persson, A., “Ruthenium- and Enzyme-Catalyzed Dynamic Kinetic Resolution F Secondary Alcohols” Journal of the American Chemical Society 121(8):1645-1650 (1999).

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