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Synfacts 2008(11): 1226-1226  
DOI: 10.1055/s-0028-1083394
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

A New Solid-Phase Linker: Cu-Assisted Amide Bond Cleavage

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Maki Minakawa
M. C. Bröhmer, W. Bannwarth*
Albert-Ludwigs-Universität Freiburg, Germany
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Publication History

Publication Date:
23 October 2008 (online)

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Significance

A chemically robust linker for solid-phase synthesis is reported, which is cleaved by Cu²+-assisted methanolysis. Thus, HypoGel-400-supported 2 underwent peptide synthesis (A), reduction amination (B), Suzuki-Miyaura coupling (C), and ring-closing metathesis (D) to give the corresponding amides 3A-D. Treatment of 3 with an equimolar amount of Cu(OTf)2 in methanol led to methanolysis of the amide bond, giving the corresponding methyl esters (5A-D) in 31-50% overall yield from 1.