DCC Mediated Direct Amidation of NSAID Naproxen, Ibuprofen and Ketoprofen with Secondary Amines

Abstract

Direct and atom-economical amidation of nonsteroidal antiinflammatory drugs naproxen ibuprofen and ketoprofen with a variety of secondary amines was effected using commercially available DCC under mild and open-air conditions. These prodrug amides were obtained in good to moderate yields ranging between 30-90 %.

Synthesis of N-glycosyl amides: conformational analysis and evaluation as inhibitors of β-galactosidase from E. coli

“…Additionally, lower yields have also been reported in similar coupling reactions using bulky acids or amines derivatives. 35,36 To improve the yields in the production of bridged disaccharide derivatives, alternative conditions were evaluated using as a model the synthesis of 16a from the glycosyl azide 5a and the thioglyco acid 13b (Table 3). The Steglich amidation was Chart 1 Carboxylic acids selected for amidation reactions with glycosyl amines 2a-c. attempted, since the use of N,N-dimethylaminopyridine (DMAP) and carbodiimides was reported to facilitate the formation of esters [37][38][39] or amides 40,41 of sterically hindered acids or lowreactivity nucleophiles (alcohols or amines).…”

“…Additionally, lower yields have also been reported in similar coupling reactions using bulky acids or amines derivatives. 35,36…”