Amino-acids condensations in the preparation of N alpha-9-fluorenylmethyloxycarbonylamino-acids with 9-fluorenylmethylchloroformate

Synthesis of N alpha-9-fluorenylmethyloxycarbonyl (Fmoc) amino-acids by reaction of free amino-acids (glycine and alanine) with 9-fluorenylmethylchloroformate leads to formation of small amounts of Fmoc-dipeptide which are difficult to eliminate by crystallization. The alternative way to prepare Fmoc-amino-acids by reacting the Fmoc-chloride first with sodium azide and then with the free amino-acid eliminates this side reaction, at least for glycine and alanine.