Synthesis of glycyl-(<i>S</i>)-5-hydroxynorvaline

Abstract

The dipeptide glycyl-( S )-5-hydroxynorvaline was obtained from 1- tert -butyl 5-methyl N -Boc-glycyl-( S )-glutamate as a result of saponification and subsequent reduction of the activated 5-carboxyl group with sodium borohydride followed by removal of the N -Boc and OBu t protecting groups by refluxing in a dioxane-water mixture. Using the example of the synthesis of ( S )-5-hydroxynorvaline, it has been shown that the used sequence of chemical transformations is not accompanied by racemization.