Azidomethyl 4-nitrophenyl carbonate-A reagent for the one-step introduction of the azidomethyloxycarbonyl (Azoc) protecting group

Article abstract of DOI:10.1055/s-0030-1258049

Presented here is the three-step synthesis of azidomethyl 4-nitrophenyl carbonate in 58% overall yield. This carbonate allows for the high-yielding (≥90%) introduction of the phosphine-labile azidomethyloxycarbonyl (Azoc) protecting group in one step. The reagent protects a range of amines, including amino acids. For nonionic substrates, pure carbamates are obtained after extractive workup. Georg Thieme Verlag Stuttgart - New York.