110969-41-0Relevant articles and documents
Selective Cleavage of Boc-acylamides. A Novel Approach to Deacylation of Carboxamides
Grehn, Leif,Gunnarsson, Kerstin,Ragnarsson, Ulf
, p. 18 - 23 (2007/10/02)
Boc (tert-butoxycarbonyl) derivatives were recently prepared from various amides.This paper describes some of their properties with particular attention to mild amide cleavage.Boc-protected carboxamides were cleaved by aminolysis with complete selectivity to give the corresponding tert-butyl carbamates.The amines used ranged from hydrazine to morpholine, but for preparative purposes 2-diethylaminoethylamine was preferred.A simple two-step one-pot procedure for tert-butoxycarbonylation followed by aminolysis was developed which could be used for removal of formyl, ace tyl, and benzoyl groups.In extreme cases, there derivatives were cleaved by alcoholysis.Upon addition of bases such as N,N,N',N'-tetramethylguanidine (TMS) this reaction became very fast.TMS-catalysed methanolysis gave 98percent cleavage in 30 min or less in two preparative experiments.