Novel deprotection method of Fmoc group under the mild hydrogenation condition

ORGN 193

Yuuta Fujiwara, yakuhin@gifu-pu.ac.jp, Hiroyoshi Esaki, Takashi Ikawa, Tomohiro Maeagwa, maegawa@gifu-pu.ac.jp, Yasunari Monguchi, and Hironao Sajiki, sajiki@gifu-pu.ac.jp. Department of Medicinal Chemistry, Gifu Pharmaceutical University, 6-1, Mitahora-higashi 5-chome, Gifu, 502-8585, Japan

Fmoc (9-fluorenylmethoxycarbonyl) is a useful protective group amino acids and Fmoc-protected amino acids are widely utilized as a building block for peptides synthesis. Usually, the Deprotection of Fmoc can be achieved under basic conditions in the presence of piperidine or morpholine as a base. Therefore, Fmoc protective group could not be applicable to the substrates containing base labile functional groups. During the course of our study to develop the hydrogenation using heterogeneous Pd/C catalyst, we found that the Fmoc protective group was cleaved under the neutral Pd/C catalyzed hydrogenation conditions at room temperature. Interestingly, the addition of MeCN into the reaction mixture dramatically accelerated the reaction rate. The present reductive method is applicable as a mild and general Fmoc deprotection method.