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

C - Chemistry, Metallurgy

07

C

C07C 237/06 (2006.01) C07C 231/12 (2006.01) C07C 231/16 (2006.01)

Patent

CA 2163931

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 conden- sation with an aryl aldehyde to form a Schiff's base, which is racemized at the amino acid moiety in the presence of a base promoting racemization 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 D-amino acid-(S)-amide and the starting aldehyde. The method of the invention enables one to prepare D-amino acid-M-(S)-.alpha.-alkylbenzylamides of the formula: Image (I) wherein the carbon atom indicated by an asterisk (*) has a D-amino acid structure, R1 is an alkyl group having from 1 to 4 carbon atoms and R2 is a methyl or ethyl group, which can be used as intermediates for the preparation of substances having intense sweetness.

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