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Communication | Regular issue | Vol 36, No. 8, 1993, pp.1729-1734
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6398
Mild and Chemoselective Cleavage of p-Nitrobenzyl Esters and p-Nitrobenzyloxycarbonyl Amines with Zinc Dust

Toshio Kumagai,* Takao Abe, Yukari Fujimoto, Takaaki Hayashi, Yoshinori Inoue, and Yoshimitsu Nagao*

*Faculty of Pharmaceutical Sciences, University of Tokushima, Sho-machi, Tokushima 770-8505, Japan

Abstract

p-Nitrobenzyl esters and p-nitrobenzyloxycarbonyl amines have been efficiently deprotected by treatment with zinc dust in THF - 0.35 M phosphate buffer solution (pH 6) to obtain the parent carboxylic acids and amines. Olefinic bond, S-N bond, and diphenylmethyl- and benzyloxycarbonylamino groups are intact under the deprotection conditions.