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Devocelle M, McLoughlin BM, Sharkey CT, et al. A convenient parallel synthesis of low molecular weight hydroxamic acids using polymer-supported 1-hydroxybenzotriazole. Org Biomol Chem. 2003;1(5):850-3doi: 10.1039/b211526c.
Devocelle, M., McLoughlin, B. M., Sharkey, C. T., Fitzgerald, D. J., & Nolan, K. B. (2003). A convenient parallel synthesis of low molecular weight hydroxamic acids using polymer-supported 1-hydroxybenzotriazole. Organic & biomolecular chemistry, 1(5), 850-3. https://doi.org/10.1039/b211526c
Devocelle, Marc, et al. "A convenient parallel synthesis of low molecular weight hydroxamic acids using polymer-supported 1-hydroxybenzotriazole." Organic & biomolecular chemistry vol. 1,5 (2003): 850-3. doi: https://doi.org/10.1039/b211526c
Devocelle M, McLoughlin BM, Sharkey CT, Fitzgerald DJ, Nolan KB. A convenient parallel synthesis of low molecular weight hydroxamic acids using polymer-supported 1-hydroxybenzotriazole. Org Biomol Chem. 2003 Mar 07;1(5):850-3. doi: 10.1039/b211526c. PMID: 12929369.
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Org Biomol Chem. 2003 Mar 07;1(5):850-3. doi: 10.1039/b211526c.

A convenient parallel synthesis of low molecular weight hydroxamic acids using polymer-supported 1-hydroxybenzotriazole.

Organic & biomolecular chemistry

Marc Devocelle, Brian M McLoughlin, Caroline T Sharkey, Desmond J Fitzgerald, Kevin B Nolan

Affiliations

  1. Centre for Synthesis and Chemical Biology, Department of Chemistry, Royal College of Surgeons in Ireland, 123 St. Stephen's Green, Dublin 2, Ireland. [email protected]

PMID: 12929369 DOI: 10.1039/b211526c

Abstract

A convenient two-step procedure for the parallel synthesis of hydroxamic acids from carboxylic acids and hydroxylamine in good to high yields is reported. It involves the formation of a polymer-bound HOBt active ester and subsequent reaction with O-protected or free hydroxylamine. The hydroxamates are isolated with high purities by simple evaporation of volatile solvents. The use of free hydroxylamine leads to increased yields while maintaining high purities. Recycling of the spent resin to produce the same or a different hydroxamic acid has been achieved by a three-step protocol which is easily amenable to automation and cost-economical. The method presented here is well suited to the preparation of the title compounds and can be used effectively to synthesise large molecules containing a hydroxamic acid group.

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