N-Chlorosuccinimide-Mediated Oxidative Chlorination of Thiols to Nα -Protected Amino Alkyl Sulfonyl Azides and Their Utility in the Synthesis of Sulfonyl Triazole Acids

Title:N-Chlorosuccinimide-Mediated Oxidative Chlorination of Thiols to Nα -Protected Amino Alkyl Sulfonyl Azides and Their Utility in the Synthesis of Sulfonyl Triazole Acids

Volume: 24 Issue: 1

Author(s): Sharnabai. K. M, Krishnamurthy. M, Sagar. N. R, Santhosh. L and Vommina V. Sureshbabu

Affiliation:

Keywords: N^α-protected thiols, N^α-protected amino alkyl sulfonyl azides, sulfonyl triazole acid, Click reaction.

Abstract: An efficient oxidative chlorination of thiols to N^α-protected amino alkyl sulfonyl azides is delineated. The reaction involves in situ generation of sulfonyl chloride employing Nchlorosuccinimide and tetrabutylammonium chloride-water in acetonitrile, followed by the reaction with sodium azide. The protocol is simple, straight forward, mild and high yielding. Amino acids with simple as well as bifunctional side chains were used to obtain N^α-protected amino alkyl sulfonyl azides. Further, sulfonyl azides were utilized to synthesize unnatural amino acids via Cu(OAc)₂.H₂O/2-amino phenol catalyzed Click reaction with propiolic acid.

Cite this article as:

K. M Sharnabai., M Krishnamurthy., N. R Sagar., L Santhosh. and Sureshbabu V. Vommina, N-Chlorosuccinimide-Mediated Oxidative Chlorination of Thiols to Nα -Protected Amino Alkyl Sulfonyl Azides and Their Utility in the Synthesis of Sulfonyl Triazole Acids, Protein & Peptide Letters 2017; 24 (1) . https://dx.doi.org/10.2174/0929866523666161130151218

DOI https://dx.doi.org/10.2174/0929866523666161130151218	Print ISSN 0929-8665
Publisher Name Bentham Science Publisher	Online ISSN 1875-5305