Deprotection of 2-nitrobenzenesulfonamides using fluorous and solid phase reagents

Tetrahedron Letters

Volumn 45, Issue 43, 2004, Pages 7991-7993

  Christensen, Caspar ^a   Clausen, Rasmus P ^a   Begtrup, Mikael ^a   Kristensen, Jesper L ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

2 Nitrobenzenesulfonamides; Deprotection; Fluorous reagents

Indexed keywords

AMIDE; AMINE; FLUORINE DERIVATIVE; SILICA GEL; SULFONAMIDE; SULFONE DERIVATIVE; THIOL;

ARTICLE; DEPROTECTION REACTION; FLUORINATION; SOLID PHASE EXTRACTION;

EID: 4644292135     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.09.015     Document Type: Article

References (6)

1. T. Fukuyama, M. Cheung, C.K. Jow, Y. Hidai, and T. Kan Tetrahedron Lett. 38 1997 5831 5834
2. Review: T. Kan, and T. Fukuyama Chem. Commun. 2004 353 359
3. Perfluorinated compounds and cartridges can be obtained from Fluorous Technologies Inc
4. Review: W. Zhang Tetrahedron 59 2003 4475 4489
5. 3, 300 MHz): δ 8.25 (1H, dd, J = 8.2, 1.5 Hz), 7.63 (1H, m), 7.41-7.31 (m, 2H), 3.26-3.20 (m, 2H), 2.59-2.42 (m, 2H)
6. Representative experimental procedure: To a solution of N-(2-nitrobenzenesulfonyl)-phenylalanine (100 mg, 0.29 mmol) and Amberlyst A-21 (L = 1 mmol/g, 10 equiv) in MeCN (3 mL) ethyl thioglycolate (170 mg, 5 equiv) was added and the mixture was stirred at rt for 48 h. The resulting yellow solution was filtered and the resin eluted with MeCN. Then, the resin was eluted with AcOH/MeCN (1/1) and the resulting filtrate was evaporated in vacuo to afford pure phenylalanine in 65% yield with spectral data identical to those of an authentic sample