Method of preparing D-amino acid-N-(S)-.alpha.-alkylbenzylamide

Details Method of preparing D-amino acid-N-(S)-.alpha.-alkylbenzylamide Method of preparing D-amino acid-N-(S)-.alpha.-alkylbenzylamide

1995-11-16

1997-10-21

Kumar, Shailendra

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

Organic compounds

Amino nitrogen containing

564164, 564165, 564194, 564196, 564198, 564424, 564425, C07C23118

Patent

active

056798571

ABSTRACT:
L-amino acid amides are converted to the corresponding D-amino acid amides. An amide formed from an L-amino acid and an optically active (S)-.alpha.-alkylbenzylamine is subjected to dehydration condensation with an aryl aldehyde to form a Schiff's base, which is racemized at the amino acid moiety in the presence of a base to yield an N-allylidene-D-amino acid-(S)-amide. The less-soluble diastereomer N-allylidene-D-amino acid-(S)-amide is crystallized from the reaction mixture and recovered by means of solid/liquid separation. The N-allylidene form is readily hydrolyzed into the amino acid-(S)-amide and the starting aldehyde.

REFERENCES:
patent: 5306826 (1994-04-01), Boesten
Patent Abstracts of Japan, vol. 10, No. 144 (C-349) (2201), May 27, 1986, JP-61-1652, Jan. 7, 1986.

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