Process for the production of...

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C - Chemistry, Metallurgy

07

D

C07D 209/48 (2006.01) C07C 227/32 (2006.01) C07C 229/22 (2006.01) C07C 229/28 (2006.01) C07C 229/34 (2006.01) C07C 255/42 (2006.01)

Patent

CA 2083108

ABSTRACT OF THE DISCLOSURE A process is disclosed for the production of .alpha.- hydroxy-.beta.-aminocarboxylic acids of the formula: Image (I) starting from N-protected .alpha.-amino acid halides of the formula: Image (II) The process comprises converting the halides (II) with trimethylsilyl cyanide into novel .alpha.-oxonitriles (acyl cyanides). In a second step, the acyl cyanides are converted into novel .alpha.-oxo-carboxylic acid esters and then reduced selectively to .alpha.-hydroxycarboxylic acid esters. The .alpha.-hydroxycarboxylic acid esters are optionally separated into their diastereomers and/or are subjected to a cleaving off of the N-protective group and/or to an ester hydrolysis. The .alpha.-hydroxy-.beta.-amino-carboxylic acids (I) are structural elements of peptides with enzyme inhibiting effect.

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