Synthesis of conformationally constrained diaminodicarboxylic acid derivatives

Robin A. Weatherhead, Michael D. Carducci, Eugene A Mash

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Abstract

(Chemical Presented) Functionally protected forms of three conformationally constrained diaminodicarboxylic acids were synthesized and characterized. 2,2′-Diaminospiro[3.3]heptane-2,2′-dicarboxylic acid, an analogue of diaminopimelic acid, was prepared in racemic form and the structure established by X-ray crystallographic analysis of the methyl ester hydrochloride. trans-1,4-Diaminocyclohexane-1,4-dicarboxylic acid was prepared and its structure established by X-ray crystallographic analysis of the corresponding Cbz-protected ethyl ester. cis- and trans-2,6-diamino-1,2,3,5,6,7-hexahydro- sindacene-2,6-dicarboxylic acids were synthesized and the structures assigned by X-ray crystallographic analysis of the corresponding Boc-protected ethyl ester and Cbz-protected ethyl ester, respectively.

Original languageEnglish (US)
Pages (from-to)8773-8778
Number of pages6
JournalJournal of Organic Chemistry
Volume74
Issue number22
DOIs
Publication statusPublished - Nov 20 2009

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ASJC Scopus subject areas

  • Organic Chemistry

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