Development of a mild amide-cleavage reaction

2015 Fiscal Year Final Research Report

• Project/Area Number: 25460012
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: Kanazawa University
• Principal Investigator: Yamada Kohei 金沢大学, 薬学系, 助教 (40583232)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Keywords: アミド切断 / ベンジルカチオン / ベンジル化剤 / DPT-BM

Outline of Final Research Achievements

A mild method for amide-cleavage using DPT-BM, which spontaneously releases benzyl cation species when dissolved at room temperature, was developed. Benzylation of the amide with DPT-BM and the subsequent hydrolysis of the resulting intermediate benzyl imidate salt affords the corresponding amine and benzyl ester, which can be converted by hydrogenolysis into a carboxylic acid under neutral conditions. Benzylation proceeds depending on both steric and electronic factors around the amide group. Thus, some amides have been selectively cleaved over other amides. Furthermore, intramolecular chemoselective cleavage of an amide group in the presence of an ester group was achieved.

Free Research Field

有機合成化学