Thio acid/azide amidation: an improved route to N-acyl sulfonamides.
A one-pot procedure for the conversion of carboxylic acids to N-acyl sulfonamides, via thio acid/azide amidation, is presented. The method is compatible with acid- and base-sensitive amino acid protection. N-Acyl sulfonamide synthesis on solid support, peptide thio acid/sulfonazide coupling, and N-alkyl amide synthesis via selective cleavage of sulfonyl from an N-alkyl-N-acyl sulfonamide are also reported.
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, USA.
Kristin N
KN
Barlett
Robert V
RV
Kolakowski
Sreenivas
S
Katukojvala
Lawrence J
LJ
Williams
D000577:Amides / Q000737:chemistry* / Q000145:classification; D000596:Amino Acids / Q000737:chemistry; D001386:Azides / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry
D000577:Amides; D000596:Amino Acids; D001386:Azides; D002264:Carboxylic Acids; D010455:Peptides; D013449:Sulfonamides