Efficient cleavage of carboxylic tert-butyl and 1-adamantyl esters, and N-Boc-amines using H2SO4 in CH2Cl2

被引:32
作者
Strazzolini, P [1 ]
Misuri, N [1 ]
Polese, P [1 ]
机构
[1] Univ Udine, Dept Chem Sci & Technol, I-33100 Udine, Italy
关键词
sulfuric acid; dichloromethane; deprotection; tert-butyl ester; N-Boc-amine;
D O I
10.1016/j.tetlet.2005.01.129
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new procedure for the deprotection of carboxylic tert-butyl and 1-adamantyl esters, and N-Boc-amines using H2SO4 in CH2Cl2 is described. The proposed method is simple, cheap, eco-friendly and represents a valid alternative to existing ones, with special significance in large scale applications. (C) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2075 / 2078
页数:4
相关论文
共 39 条
  • [1] Adrián F, 1999, EUR J INORG CHEM, P2347
  • [2] SELECTIVE PROTECTION OF POLYAMINES - SYNTHESIS OF MODEL COMPOUNDS AND SPERMIDINE DERIVATIVES
    ALMEIDA, MLS
    GREHN, L
    RAGNARSSON, U
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (07): : 1905 - 1911
  • [3] REDUCTIVE DEOXYGENATION OF ESTERS WITH TRICHLOROSILANE
    BALDWIN, SW
    HAUT, SA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (26) : 3885 - 3887
  • [4] BODANSZKY M, 1984, PRINCIPLES PEPTIDE S, V16, P78
  • [5] Bonini BF, 1998, SYNLETT, P1013
  • [6] THE USE OF PARA-TOLUENESULFONIC ACID FOR REMOVAL OF THE N-TERT-BUTOXYCARBONYL PROTECTING GROUP IN SOLID-PHASE PEPTIDE-SYNTHESIS
    BRINKMAN, HR
    LANDI, JJ
    PATERSON, JB
    STONE, PJ
    [J]. SYNTHETIC COMMUNICATIONS, 1991, 21 (03) : 459 - 465
  • [7] NUCLEAR ANALOGS OF BETA-LACTAM ANTIBIOTICS .2. TOTAL SYNTHESIS OF 8-OXO-4-THIA-1-AZABICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACIDS
    BRYAN, DB
    HALL, RF
    HOLDEN, KG
    HUFFMAN, WF
    GLEASON, JG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (07) : 2353 - 2355
  • [8] Stereoselective synthesis of a C-glycosidic analog of N-glucoasparagine
    Burkhart, F
    Hoffmann, M
    Kessler, H
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (11): : 1191 - 1192
  • [9] NEW METHODS OF INTRODUCING CARBO-TERT-BUTOXY AMINO-PROTECTING GROUP . INVESTIGATION OF TERT-ALKYL CHLOROFORMATES SUBSTITUTED WITH ELECTRON-WITHDRAWING SUBSTITUENTS
    CARPINO, LA
    PARAMESW.KN
    KIRKLEY, RK
    SPIEWAK, JW
    SCHMITZ, E
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (10) : 3291 - +
  • [10] FACILE SYNTHESIS OF TERT-BUTYL ESTER OF N-PROTECTED AMINO-ACIDS WITH TERT-BUTYL BROMIDE
    CHEVALLET, P
    GARROUSTE, P
    MALAWSKA, B
    MARTINEZ, J
    [J]. TETRAHEDRON LETTERS, 1993, 34 (46) : 7409 - 7412