[biggestdav]

Hi can anyone tell me the mechanism for DMAP N-boc protection in imidazoles using boc anhydride? Does it reacts with the Boc2O displacing one of the tertbutoxy groups to form a more reactive compound or is it simply acting as a base deprotonating the nitrogen?

Many thanks

dave

[nj_bartel]

It isn't just a proton sink for the now quanternary imidazolium nitrogen, is it?

[Smrt guy]

catalytic DMAP is sometimes used in corroboration with an acylating agent to increase the reactivity.  The ring N is acylated first then later displaced by an appropriate nucleophile