Process for preparation of an optically active amino acid amide

Details Process for preparation of an optically active amino acid amide Process for preparation of an optically active amino acid amide

1991-02-15

1994-04-26

Brust, Joseph Paul

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

562401, 562402, 564164, 564165, 564198, 564303, 564424, 564425, C07C23120

Patent

active

053068262

ABSTRACT:
The present invention relates to a process for the preparation of optically active amino acid amide. L-amino and D-amino acid amides are mixed in the presence of 0.5-4 equivalents of an aldehyde, relative to the quantity of amino acid amide, in the presence of a solvent and water. The mixture is converted in whole or in part by means of an optically active carboxylic acid into a salt of the amino acid amide and the carboxylic acid. A portion mainly consisting of one of the diastereoisomers of that salt is separated from the reaction mixture obtained. Instead of a mixture of L-amino and D-amino acid amides, it is also possible to use a mixture of the Schiff bases of an amino acid amide and an aldehyde, in which case it is not necessary to add extra aldehyde, and the required quantity of water amounts to at least 1 equivalent relative to the quantity of Schiff base. With this process, a high yield of optically active amino acid amide or the corresponding amino acid is rapidly obtained.

REFERENCES:
patent: 3976680 (1976-08-01), Clark et al.
patent: 4072698 (1978-02-01), Hylton et al.
patent: 4093653 (1978-06-01), Boesten
patent: 4275217 (1981-06-01), Duhamel et al.
patent: 4285884 (1981-08-01), Dannenberg et al.
Jacques, et al., Enantiomers, Racemates, and Resolutions; Chapter 6, pp. 369-377. (no date given nor can one be found).
Noller, "Chemistry of Organic Compounds", (1965), 3rd Ed., p. 439.

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