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
  • [31] tert-Butoxycarbonyl Chloride for the Introduction of N-Boc Groups into Amino Acids
    Vorbrueggen, Helmut
    SYNTHESIS-STUTTGART, 2008, (23): : 3739 - 3741
  • [32] ESTERIFICATION OF CARBOXYLIC ACIDS USING A BORON TRIFLUORIDE-ETHERATE-ALCOHOL REAGENT
    MARSHALL, JL
    ERICKSON, KC
    FOLSOM, TK
    TETRAHEDRON LETTERS, 1970, (46) : 4011 - &
  • [33] STUDIES ON PARTHENIN - REACTIONS OF N-BROMOSUCCINIMIDE AND BORON-TRIFLUORIDE ETHERATE ON PARTHENIN
    SETHI, VK
    THAPPA, RK
    DHAR, KL
    ATAL, CK
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1983, 22 (05): : 494 - 495
  • [34] A fast and practical synthesis of tert-butyl esters from 2-tert-butoxypyridine using boron trifluoride•diethyl etherate under mild conditions
    Minh Thanh La
    Kim, Hee-Kwon
    TETRAHEDRON, 2018, 74 (27) : 3748 - 3754
  • [35] Formation of Arginine Modifications in a Model System of Nα-tert-Butoxycarbonyl (Boc)-Arginine with Methylglyoxal
    Kloepfer, Antje
    Spanneberg, Robert
    Glomb, Marcus A.
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2011, 59 (01) : 394 - 401
  • [36] A N-ACETYL GROUP MORE LABILE TO METHANOLIC HYDROGEN-CHLORIDE THAN AN ANALOGOUS N-TERT-BUTOXYCARBONYL GROUP
    HOWARD, JC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1981, 181 (MAR): : 195 - ORGN
  • [37] COMPARISON OF THE ALLYLATION REACTIONS OF ALDEHYDES USING ALLYLSTANNANES WITH BORON-TRIFLUORIDE ETHERATE AND BORON-TRICHLORIDE
    MARTON, D
    TAGLIAVINI, G
    ZORDAN, M
    WARDELL, JL
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 390 (02) : 127 - 138
  • [38] Coliquefaction of Coal and Waste Plastic Using Boron Trifluoride Etherate as Catalyst at Moderate Conditions
    Du, Kun
    Zhang, Jianxin
    Wang, Daoping
    Fan, Zhifang
    Li, Zhi
    SOLID FUEL CHEMISTRY, 2013, 47 (06) : 375 - 383
  • [39] SELECTIVE TRANSFORMATION OF N-TERT-BUTOXYCARBONYL GROUP INTO N-ALKOXY-CARBONYL GROUP VIA N-CARBOXYLATE ION EQUIVALENT
    SAKAITANI, M
    OHFUNE, Y
    TETRAHEDRON LETTERS, 1985, 26 (45) : 5543 - 5546
  • [40] Coliquefaction of coal and waste plastic using boron trifluoride etherate as catalyst at moderate conditions
    Kun Du
    Jianxin Zhang
    Daoping Wang
    Zhifang Fan
    Zhi Li
    Solid Fuel Chemistry, 2013, 47 : 375 - 383