Deprotection/reprotection of the amino group in alpha-amino acids and peptides. A one-pot procedure in [Bmim][BF4] ionic liquid

作者：Di Gioia M L^*; Barattucci A; Bonaccorsi P; Leggio A; Minuti L; Romio E; Temperini A; Siciliano C

来源：RSC Advances, 2014, 4(6): 2678-2686.

DOI：10.1039/c3ra46599c

This paper presents an efficient one-pot protocol for the sequential deprotection/reprotection of the alpha-amino group in alpha-amino acid and dipeptide methyl esters. [Bmim][BF4] is used as the solvent in the entire process. In particular, the use of the ionic liquid allows for rapid and clean removal of the 4-nitrobenzenesulfonyl (nosyl) group and for facile subsequent tert-butyloxycarbonylation of the free alpha-amino function under very mild conditions. N-Boc-alpha-amino acid as well as peptide derivatives are isolated in excellent yields, and do not require any further purification. Absolute configurations of the precursors are totally preserved during the process.

• 出版日期2014