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Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology
Published on: May 15, 2012
The solid-phase synthesis and use of N-monosubstituted piperazines in chemical library synthesis
Joseph M Salvino1, Baudouin Gerard, Hai Fen Ye
1Combinatorial Chemistry Department, Adolor Corporation, 371 Phoenixville Pike, Malvern, Pennsylvania 19355, USA.
Abstract:
An efficient solid-phase synthesis of mono-N-substituted piperazines is presented. The key transformation involves a selective borane amide bond reduction in the presence of a carbamate resin linkage. This synthetic route takes advantage of the large diverse pool of commercially available carboxylic acids, acid chlorides, and sulfonyl chlorides. The solid-phase approach facilitates parallel processing by eliminating the need for column chromatography after each synthetic step. The N-monosubstituted piperazines were shown to react with polymeric activated tetrafluorophenol (TFP) reagents to generate arrays of amides and sulfonamides in good purity for biological testing.
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