PRODUCTION OF ALPHA-HYDROXY-BETA-AMINOCARBOXYLIC ACID

摘要

alpha -Hydroxy- beta -aminocarboxylic acids (I) are prepared starting from N-protected alpha -aminocarbonyl halides (II). The halides (II) are converted into the novel alpha -oxonitriles (acyl cyanides) (III) using trimethylsilyl cyanide. These alpha -oxonitriles are converted in a second step into the likewise novel alpha -oxocarboxylic acid esters (IV) and the latter are then selectively reduced to the alpha -hydroxycarboxylic acid esters (V). The alpha -hydroxycarboxylic acids are optionally separated into their diastereomers and/or subjected to removal of the N-protective group and/or to ester hydrolysis. The alpha -hydroxy- beta -aminocarboxylic acids (I) are components of peptides having enzyme inhibitor action.