Thio acid/azide amidation:: An improved route to N-acyl sulfonamides

被引:54
作者
Barlett, KN [1 ]
Kolakowski, RV [1 ]
Katukojvala, S [1 ]
Williams, LJ [1 ]
机构
[1] Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA
关键词
D O I
10.1021/ol052671d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A one-pot procedure for the conversion of carboxylic acids to N-acyl sulfonamides, via thio acid/azide amidation, is presented. The method is compatible with acid- and base-sensitive amino acid protection. N-Acyl sulfonamide synthesis on solid support, peptide thio acid/sulfonazide coupling, and N-alkyl amide synthesis via selective cleavage of sulfonyl from an N-alkyl-N-acyl sulfonamide are also reported.
引用
收藏
页码:823 / 826
页数:4
相关论文
共 44 条
[1]   Nonaromatic sulfonamide group as an ideal anchor for potent human carbonic anhydrase inhibitors: Role of hydrogen-bonding networks in ligand binding and drug design [J].
Abbate, F ;
Supuran, CT ;
Scozzafava, A ;
Orioli, P ;
Stubbs, MT ;
Klebe, G .
JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (17) :3583-3587
[2]   Acyl vs sulfonyl transfer in N-acyl β-sultams and 3-oxo-β-sultams [J].
Ahmed, N ;
Tsang, WY ;
Page, MI .
ORGANIC LETTERS, 2004, 6 (02) :201-203
[3]   An alkanesulfonamide "safety-catch" linker for solid-phase synthesis [J].
Backes, BJ ;
Ellman, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) :2322-2330
[4]   Peptide segment coupling by prior ligation and proximity-induced intramolecular acyl transfer [J].
Coltart, DM .
TETRAHEDRON, 2000, 56 (22) :3449-3491
[5]   COMPARATIVE-STUDY OF SELECTED COUPLING REAGENTS IN DIPEPTIDE SYNTHESIS [J].
DUDASH, J ;
JIANG, JJ ;
MAYER, SC ;
JOULLIE, MM .
SYNTHETIC COMMUNICATIONS, 1993, 23 (03) :349-356
[6]   2,4-dinitrobenzenesulfonamides: A simple and practical method for the preparation of a variety of secondary amines and diamines. [J].
Fukuyama, T ;
Cheung, M ;
Jow, CK ;
Hidai, Y ;
Kan, T .
TETRAHEDRON LETTERS, 1997, 38 (33) :5831-5834
[7]   Synthesis of a thioester linker precursor for a general preparation of peptide C-terminal thioacids [J].
Gaertner, H ;
Villain, M ;
Botti, P ;
Canne, L .
TETRAHEDRON LETTERS, 2004, 45 (10) :2239-2241
[8]   An alternate preparation of thioester resin linkers for solid-phase synthesis of peptide C-terminal thioacids [J].
Goldstein, AS ;
Gelb, MH .
TETRAHEDRON LETTERS, 2000, 41 (16) :2797-2800
[9]  
HAZEN GG, ORGANIC SYNTHESES, V9, P400
[10]  
HoegJensen T, 1996, SYNTHESIS-STUTTGART, P383