N-tert-butoxycarbonyl (BOC) deprotection using boron trifluoride etherate

被引:52
|
作者
Evans, EF
Lewis, NJ
Kapfer, I
Macdonald, G
Taylor, RJK
机构
[1] UNIV YORK,DEPT CHEM,YORK YO1 5DD,N YORKSHIRE,ENGLAND
[2] SMITHKLINE BEECHAM PHARMACEUT,TONBRIDGE TN11 9AN,KENT,ENGLAND
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1080/00397919708006783
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A mild and efficient procedure is described for the removal of the tert-butoxycarbonyl (BOG) group using boron trifluoride etherate and molecular sieves in dichloromethane at room temperature. The scope of this procedure is explored for the deprotection of a variety of amines including amino acid derivatives.
引用
收藏
页码:1819 / 1825
页数:7
相关论文
共 50 条
  • [1] Deprotection of N-tert-butoxycarbonyl (Boc) groups in the presence of tert-butyl esters
    Lin, LS
    Lanza, T
    de Laszlo, SE
    Truong, Q
    Kamenecka, T
    Hagmann, WK
    TETRAHEDRON LETTERS, 2000, 41 (36) : 7013 - 7016
  • [2] USE OF N-TERT-BUTOXYCARBONYL (BOC) DERIVATIVES FOR THE SYNTHESIS OF NITRAMINES
    MITCHELL, AR
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 203 : 422 - ORGN
  • [3] A new protocol for selective deprotection of N-tert-butoxycarbonyl protective group (t-boc) with Sn(OTf)2
    Bose, DS
    Kumar, KK
    Reddy, AVN
    SYNTHETIC COMMUNICATIONS, 2003, 33 (03) : 445 - 450
  • [4] Deprotection of N-tert-Butoxycarbonyl (Boc) Protected Functionalized Heteroarenes via Addition-Elimination with 3-Methoxypropylamine
    Gulledge, Zachary Z.
    Carrick, Jesse D.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (12) : 1817 - 1822
  • [5] Rhodium-Catalyzed N-tert-Butoxycarbonyl (Boc) Amination by Directed CH Bond Activation
    Wippich, Julian
    Truchan, Nadina
    Bach, Thorsten
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (13) : 2083 - 2087
  • [6] SELECTIVE CLEAVAGE OF N-TERT-BUTOXYCARBONYL PROTECTING GROUP
    KINOSHIT.H
    KOTAKE, H
    CHEMISTRY LETTERS, 1974, (06) : 631 - 634
  • [7] Lewis acid-mediated selective removal of N-tert-butoxycarbonyl protective group (t-Boc)
    Bose, DS
    Lakshminarayana, V
    SYNTHESIS-STUTTGART, 1999, (01): : 66 - 68
  • [8] Large scale deprotection of a tert-butoxycarbonyl (Boc) group using aqueous HCl and acetone
    Coffey, DS
    Hawk, MKN
    Pedersen, SW
    Ghera, SJ
    Marler, PG
    Dodson, PN
    Lytle, ML
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2004, 8 (06) : 945 - 947
  • [9] Development of a Practical Synthetic Method for N-tert-Butoxycarbonyl α-Ketimino Esters
    Hashimoto, Takuya
    Yamamoto, Kumiko
    Maruoka, Keiji
    CHEMISTRY LETTERS, 2011, 40 (03) : 326 - 327
  • [10] Selective conversion of N-trichloroethoxycarbonyl (Troc) groups into N-acetyl groups in the presence of N-tert-butoxycarbonyl (Boc) protecting groups
    Zhu, XM
    Schmidt, RR
    SYNTHESIS-STUTTGART, 2003, (08): : 1262 - 1266