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

被引：31

作者：

Di Gioia, M. L. ^{[1
]}

Barattucci, A. ^{[2
]}

Bonaccorsi, P. ^{[2
]}

Leggio, A. ^{[1
]}

Minuti, L. ^{[3
]}

Romio, E. ^{[1
]}

Temperini, A. ^{[4
]}

Siciliano, C. ^{[1
]}

机构：

[1] Univ Calabria, Dipartimento Farm & Sci Salute & Nutr, I-87030 Cosenza, Italy

[2] Univ Messina, Dipartimento Sci Chim, I-98166 Messina, Italy

[3] Univ Perugia, Dipartimento Chim, I-06123 Perugia, Italy

[4] Univ Perugia, Dipartimento Chim & Tecnol Farmaco, I-06123 Perugia, Italy

来源：

RSC ADVANCES | 2014年 / 4卷 / 06期

关键词：

N-BOC PROTECTION; HIGHLY EFFICIENT; TERT-BUTOXYCARBONYLATION; TMC-95A ANALOGS; METHYL-ESTERS; CATALYST; HYDROGEN; DESIGN;

D O I：

10.1039/c3ra46599c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：2678 / 2686

页数：9

共 14 条

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