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

作者：Fernando Rasika; Shirley Jonathan M; Torres Emilio; Jacobs Hollie K; Gopalan Aravamudan S^*

来源：Tetrahedron Letters, 2012, 53(47): 6367-6371.

DOI：10.1016/j.tetlet.2012.09.025

• Polyhydroxamate chelators
• Isocyanate
• Carbamate
• Urea

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.

• 出版日期2012-11-21