Solid-phase synthesis of biologically interesting compounds containing hydroxamic acid moiety

Viktor Krchnák1

  • 1Department of Chemistry and Biochemistry, 251 Nieuwland Science Center, University of Notre Dame, Notre Dame, IN 46556, USA. vkrchnak@nd.edu

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Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic acid...
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Acid-catalyzed hydrolysis:
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Preparation of Carboxylic Acids: Hydrolysis of Nitriles

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Hydrolysis, a cornerstone of phase I biotransformation reactions, uses water to cleave chemical bonds. This process is pivotal in drug metabolism, generating more polar metabolites that can be easily excreted.
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