129589-65-7Relevant academic research and scientific papers
A Simple Method for the Protection of Aryl Amines as their t-Butylcarbamoyl (Boc) Derivatives
Kelly, Terence A.,McNeil, Daniel W.
, p. 9003 - 9006 (2007/10/02)
It has been found that aryl amines can be directly protected as their Boc derivatives by treatment of the amine with two equivalents of NaHMDS in THF followed by one equivalent of di-t-butyldicarbonate.This procedure works on a wide variety of both electron-rich and electron-deficient aryl amines.
Metallation of N-(Pivaloyl)- and N-(tert-Butoxycarbonyl)difluoroanilines: Regiocontrol by Fluorine in the Synthesis of 4-Methoxycarbonyl Derivatives
Thornton, Timothy J.,Jarman, Michael
, p. 295 - 299 (2007/10/02)
Methyl 2,6-difluoro-4-(pivaloylamino)benzoate (3) and the corresponding 4-(tert-butoxycarbonylamino)-analogue 6 have been synthesised by reacting the appropriate 3,5-difluoroaniline derivatives with butyllithium followed by methyl chloroformate.N-(tert-Butoxycarbonyl)-2,3-difluoroaniline (9) required the "super-basic" butyllithium/potassium tert-butoxide mixture to convert it into methyl 4-(tert-butoxycarbonylamino)-2,3-difluorobenzoate (14): the 2,5-difluoro-analogue was formed in a similar manner.In all cases the regiocontrol of metallation was directed by fluorine rather than by the amide substituent.
