Deprotection/reprotection of the amino group in α-amino acids and peptides. A one-pot procedure in [Bmim][BF₄] ionic liquid
2013
Di Gioia, M. L. | Barattucci, A. | Bonaccorsi, P. | Leggio, A. | Minuti, L. | Romio, E. | Temperini, A. | Siciliano, C.
This paper presents an efficient one-pot protocol for the sequential deprotection/reprotection of the α-amino group in α-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 α-amino function under very mild conditions. N-Boc-α-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.
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