Sulfonamide Synthesis via Oxyma‐O‐sulfonates – Compatibility to Acid Sensitive Groups and Solid‐Phase Peptide Synthesis. Issue 13 (13th March 2013)

• Record Type: Journal Article
• Authors: Palakurthy, Nani Babu; Dev, Dharm; Rana, Shubhasmin; Nadimpally, Krishna Chaitanya; Mandal, Bhubaneswar
• Is Part Of: European journal of organic chemistry. Issue 13(2013)
• Page Start: 2627
• Page End: 2633
• Publication Date: 2013-03-13
• Subjects: Medicinal chemistry -- Synthesis design -- Solid‐phase synthesis -- Sulfon­amides -- Esters -- Peptides; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201201571
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A milder and more efficient procedure for the synthesis of sulfonamides by activating sulfonic acid groups as the corresponding sulfonate esters of ethyl 2‐cyano‐2‐(hydroxyimino)acetate (Oxyma) is reported. This method is greener than all other existing protocols for the purpose. Other important advantages lie in (a) its applicability to less nucleophilic anilines under ambient and milder conditions and (b) its compatibility with solid phase peptide synthesis and acid‐labile groups such as trityl (Trt) and t Bu, which empowers the solid phase synthesis of sulfonamides of various peptides. To illustrate this, the syntheses of three sulfonamide derivatives of the peptide GAILG‐NH2, which is relevant in the context of drug design against type 2 diabetes, are demonstrated by using Fmoc‐based solid‐phase peptide synthesis (SPPS). Abstract : The activation of sulfonic acids as their corresponding O ‐sulfonate esters facilitates sulfonamide synthesis, which can be applied to those substrates that possess acid‐labile functional groups and is compatible with solid phase synthesis.