Download PDF
Synfacts 2005(2): 0260-0260  
DOI: 10.1055/s-2005-916098
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

TMUCl Cl, the Efficient Reagent for the Solid-Phase Synthesis of Anilides

Contributor(s): Yasuhiro Uozumi, Masahiro Kimura
M. Vendrell, R. Ventura, A. Ewenson, M. Royo*, F. Albericio*
University of Barcelona, Spain, and Luxembourg Industries Ltd, Israel
Further Information

Publication History

Publication Date:
25 October 2005 (online)

    Permissions and Reprints

Significance

The solid-phase synthesis of anilides was performed by use of N-[chloro(dimeth­ylamino)methylene]-N-methylmethanaminium chloride (TMUCl Cl), which was identified to be an efficient reagent for the activation of solid-supported carboxylic acid. Thus, Ac-Glu(OH)-Rink-PS-resin 1 was treated with both 10 equivalents of TMUCl Cl and N,N-diisopropylethylamine (DIPEA) for activation of the carboxylic acid group followed by the reaction with 5 equivalents of 4-nitroaniline for 2 h to give 4-nitroanilide. The purity of the anilide was determined by RP-HPLC analysis after cleavage with TFA-H2O to be 78%.