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Beilstein J Org Chem. 2013;9:260-4. doi: 10.3762/bjoc.9.31. Epub 2013 Feb 6.

From bead to flask: Synthesis of a complex β-amido-amide for probe-development studies.

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1
Department of Chemistry, University of California, Davis, CA 95616, USA ; Comparative Pathology Graduate Group, University of California, Davis, CA 95616, USA.

Abstract

A concise synthesis of benzimidazole-substituted β-amido-amide LLW62 is presented. The original synthesis of compounds related to LLW62 was developed on Rink resin as part of a "one-bead, one-compound" combinatorial approach for on-bead screening purposes. The current synthesis is carried out in solution and is amenable to scale-up for follow-up studies on LLW62 and investigations of related structures. The key step involves the use of a β-amino acid-forming three-component reaction (3CR), the scope of which defines its role in the synthetic strategy.

KEYWORDS:

benzimidazole; multicomponent reaction; β-amino acid

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