Hydroxamic Acid Derivative for Selective Deacylation Reactions

N-Methyl-2-dimethylaminoacetohydroxamic acid (1) is known as a reagent for selective deacylations.¹⁾ In a water-including solvent or an alcohol, active esters like aryl esters can be selectively removed by the treatment of 1 with a substrate. This reaction is applicable to substrates like 2, which has both an alkyl ester moiety and an aryl ester moiety, and can selectively remove the acyl groups of aryl ester moiety only.²⁾ Conventional deacylation reactions require acidic or basic conditions, but this reaction can proceed under a neutral condition at room temperature. So 1 is effective to remove acyl groups under mild conditions.

Related Product

M1316

N-Methyl-2-dimethylaminoacetohydroxamic Acid

References

• 1) N-methyl-2-dimethylaminoacetohydroxamic acid as a new reagent for the selective cleavage of active esters under neutral conditions
  • M. Ono, I. Itoh, Tetrahedron Lett. 1989, 30, 207.
• 2) Inhibition of Heat Shock Induction of Heat Shock Protein 70 and Enhancement of Heat Shock Protein 27 Phosphorylation by Quercetin Derivatives
  • R. E. Wang, J. L.-F. Kao, C. A. Hilliard, R. K. Pandita, J. L. R. Roti, C. R. Hunt, J.-S. Taylor, J. Med. Chem. 2009, 52, 1912.

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