Synfacts 2011(3): 0345-0345  
DOI: 10.1055/s-0030-1259457
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Traceless Solid-Phase Click Synthesis of NH-1,2,3-Triazoles

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Maki Minakawa
A. E. Cohrt, J. F. Jensen, T. E. Nielsen*
Technical University of Denmark, Lyngby, Denmark
Further Information

Publication History

Publication Date:
16 February 2011 (online)

Significance

Resin-supported azido linkers for the preparation of NH-1,2,3-triazoles were developed. Rink-like azido resins of a variety of common polymer supports 1a-g (7 examples) were tested for the preparation of a triazole-linked ­amino acid 3. Eventually, the PEGA800-supported azido linker 1a efficiently led to the resin-anchored triazole 2a via azide-alkyne cycloaddition and subsequent Fmoc synthesis. Treatment of 2 with TFA gave the triazole-linked amino acids 3. The present method was applied to the synthesis of the Leu-enkephalin derivative 4 (80% yield with 85% purity from 1a).