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. 2012 Nov 21;53(47):6367-6371.
doi: 10.1016/j.tetlet.2012.09.025.

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

Rasika Fernando  1 , Jonathan M Shirley, Emilio Torres, Hollie K Jacobs, Aravamudan S Gopalan
Affiliations

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

Rasika Fernando et al. Tetrahedron Lett. .

Abstract

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.

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Figures

Figure 1
Figure 1
Proposed synthetic scheme
Scheme 1
Scheme 1
Scheme 2
Scheme 2
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Scheme 3
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Scheme 4
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Scheme 5
Scheme 6
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Scheme 7
Scheme 7
See this image and copyright information in PMC

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