Related Experiment Video
Updated: Aug 9, 2026
Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology
Published on: May 15, 2012
A convenient parallel synthesis of low molecular weight hydroxamic acids using polymer-supported
Marc Devocelle1, Brian M McLoughlin, Caroline T Sharkey
1Centre for Synthesis and Chemical Biology, Department of Chemistry, Royal College of Surgeons in Ireland, 123 St. Stephen's Green, Dublin 2, Ireland. mdevocelle@rcsi.ie
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.
Related Concept Videos
02:40Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
02:47Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.