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
收藏
页码：2678 / 2686
页数：9
相关论文
共 50 条
  • [1] [Bmim]BF4 ionic liquid:: a novel reaction medium for the synthesis of β-amino alcohols
    Yadav, JS
    Reddy, BVS
    Basak, AK
    Narsaiah, AV
    TETRAHEDRON LETTERS, 2003, 44 (05) : 1047 - 1050
  • [2] An efficient one-pot procedure for the preparation of 1,3,4-thiadiazoles in ionic liquid [bmim]BF4 as dual solvent and catalyst
    Rostamizadeh, Shahnaz
    Aryan, Reza
    Ghaieni, Hamid R.
    Amani, Ali M.
    HETEROATOM CHEMISTRY, 2008, 19 (03) : 320 - 324
  • [3] Synthesis of Ionic Liquids [BMIM]BF4 and [BMIM]PF6 under Microwave Irradiation by One-pot
    Du, Xigang
    Du, Jinping
    Zhang, Jun
    Guo, Xuming
    Lu, Weiwei
    Yang, Zhenyu
    FUNCTIONAL MATERIALS AND NANOTECHNOLOGY, 2012, 496 : 84 - 87
  • [4] Solubility of selected dibasic carboxylic acids in water, in ionic liquid of [Bmim][BF4], and in aqueous [Bmim][BF4] solutions
    Lin, Ho-Mu
    Tien, Hsin-Yi
    Hone, Ying-Tzu
    Lee, Ming-Jer
    FLUID PHASE EQUILIBRIA, 2007, 253 (02) : 130 - 136
  • [5] [Bmim]BF4 ionic liquid: An efficient reaction medium for the one-pot multi-component synthesis of 2-amino-4, 6-diphenylpyridine-3-carbonitrile derivatives
    Mansoor, S. Sheik
    Aswin, K.
    Logaiya, K.
    Sudhan, S. P. N.
    JOURNAL OF SAUDI CHEMICAL SOCIETY, 2016, 20 (05) : 517 - 522
  • [6] An efficient one-pot three-component synthesis of imidazol-2-ones using [Bmim]BF4 ionic liquid
    Kanakaraju, S.
    Prasanna, B.
    Venkatanarayana, P.
    Chandramouli, G. V. P.
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2012, 9 (06) : 933 - 937
  • [7] An efficient one-pot three-component synthesis of imidazol-2-ones using [Bmim]BF4 ionic liquid
    S. Kanakaraju
    B. Prasanna
    P. Venkatanarayana
    G. V. P. Chandramouli
    Journal of the Iranian Chemical Society, 2012, 9 : 933 - 937
  • [8] [bmim]BF4-accelarated One-pot Synthesis of 2-amino Thiazole Derivatives
    Duc, Dau Xuan
    Chung, Nguyen Thi
    LETTERS IN ORGANIC CHEMISTRY, 2023, 20 (08) : 689 - 695
  • [9] Inhibition synergism of glycine (an amino acid) and [BMIM][BF4] (an ionic liquid) on the growth of CH4 hydrate
    Lee, Dongyoung
    Go, Woojin
    Ko, Gyeol
    Seo, Yongwon
    CHEMICAL ENGINEERING JOURNAL, 2020, 393 (393)
  • [10] [Omim][BF4], a green and recyclable ionic liquid medium for the one-pot chemoselective synthesis of benzoxazinones
    Sharifi, Ali
    Barazandeh, Mehdi
    Abaee, M. Saeed
    Mirzaei, Mojtaba
    TETRAHEDRON LETTERS, 2010, 51 (14) : 1852 - 1855
12345