109774-63-2Relevant articles and documents
A Simple Method for tert-Butoxycarbonylation of Amides
Grehn, Leif,Gunnarsson, Kerstin,Ragnarsson, Ulf
, p. 745 - 750 (2007/10/02)
The tert-butoxycarbonyl (Boc) function was conveniently introduced onto the amide nitrogen in several secondary amides using di-tert-butyl dicarbonate in dry acetonitrile with 4-dimethylaminopyridine as catalyst.Carboxamides with different acyl groups such as formyl, acetyl and benzoyl are presented as well as derivatives of carbamic acid.Examples also include other amide types: sulfonamide, sulfenamide and phosphinamide which were all smoothly converted to the corresponding Boc derivatives under these conditions.The yields were generally excellent and the resulting Boc analogues stable compounds which could be stored for months under ordinary conditions.Some stereochemical and structural aspects of this acylation are also discussed.Bulky substituents in the proximity of the amide moiety significantly retarded the reaction and in some cases no product was detected.For one compound with an activated methine group, C acylation was observed.