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The Efficient Synthesis of Azaamino Acids

Wieczerzak E., Kozlowska J., Łankiewicz L., Grzonka Z.

Polish Journal of Chemistry

2002

Vol. 76 / nr 12

1693-1697

An efficient method of synthesis of N-t-butoxycarbonyl-azaamino acid ethyl esters has been described. This method consisted of three stages including: hydrazone formation, its reduction and acylation with ethyl chloroformate. The second step - reduction of the hydrazones to the appropriate hydrazides - was the most challenging. Some reducing agents have been tested, though NaBH3CN was found to lead to the final products with the highest yields in relatively short time and even to allow the selective reduction of C-N bond in the presence of nitro group.