One-Pot Synthesis of Nα-Protected Amino/Peptide O-benzyl Hydroxamates and Acylaminoxy Dipeptides Employing Hydroxamic Acid
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The direct conversion of simple and sterically hindered Nα-protected amino/peptide hydroxamic acids to O-benzyl hydroxamates employing K2CO3, tetrabutylammonium bromide and benzyl bromide is described. In addition, Cbz-Ala-CONHOH and Cbz-Phe-CONHOH derived acylaminoxy peptides 3j and 3k have also been prepared. The method is of importance in the view of easy availability of precursors, catalyst and reaction conditions. All the products are obtained in moderate to good yields.
KeywordsNα-protected hydroxamic acids Benzyl bromide Tetrabutylammonium bromide O-benzyl hydroxamates Acylaminoxy dipeptides
We sincerely thankful to Council of Scientific and Industrial Research (CSIR) Grant No. 02(0149)/13/EMR-II Government of India, New Delhi for financial support.
Compliance with Ethical Standards
Conflict of interest
Muniyappa Krishnamurthy, Basavaprabhu, Vommina V. Sureshbabu declare that they have no conflict of interest.
Authors declare that there is no informed consent in the article.
Human and animal rights
This article does not contain any studies with human or animal subjects performed by the any of the authors
- Chimiak A, Milewska MJ, Herz W, Grisebach H, kirbyb GW, Tamm (1988) Progress in the chemistry of organic natural products. Springer, New York, p 203Google Scholar
- Duvic M, Vu J (2007) Update on the treatment of cutaneous T-cell lymphoma (CTCL): focus on vorinostat. Biol Targets Ther 1:377Google Scholar
- Emary T (1987) In: Sigel H (ed) Metal ions in biological systems, vol 7. Marcel Dekker, New York, p 77Google Scholar
- Nageswara RP, Sureshbabu VV (2014) Iodine-accelerated synthesis of Nα-urethane protected amino/peptide hydroxamic acids from amino/peptide thioacids. IJC-B 53:1430Google Scholar
- Vasantha B, Hemantha HP, Sureshbabu VV (2010) 1-Propanephosphonic acid cyclic anhydride (T3P) as an efficient promoter for the lossen rearrangement: application to the synthesis of urea and carbamate derivatives. Synthesis 17:299Google Scholar