Preparation of bifunctional isocyanate hydroxamate linkers: synthesis of carbamate and urea tethered polyhydroxamic acid chelators

TETRAHEDRON LETTERS

卷:53

Article

Fernando, Rasika¹  Shirley, Jonathan M.¹  Torres, Emilio¹  Jacobs, Hollie K.¹  Gopalan, Aravamudan S.¹ 

[1] New Mexico State Univ, Dept Chem & Biochem, Las Cruces, NM 88003 USA

关键词: Polyhydroxamate chelators;    Isocyanate;    Carbamate;    Urea;   

DOI  :  10.1016/j.tetlet.2012.09.025

来源: Elsevier

【 摘 要 】

Two novel bifunctional N-methylhydroxamate-isocyanate linkers 20 and 21 were prepared in good yield and high purity from the corresponding amine salts using a biphasic reaction with phosgene. The facile ring opening reaction of N-Boc lactams using the anion of O-benzylhydroxylamine gave the protected amino hydroxamates 6a and 6c in good yields. The selective methylation of the hydroxamate nitrogen in the presence of the N-Boc group in these intermediates could be readily accomplished. The utility of the linkers was clearly demonstrated by the synthesis of the carbamate-tethered trishydroxamic acid 27 and the urea-tethered 29. (C) 2012 Elsevier Ltd. All rights reserved.

【 授权许可】

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