Novel N-demethylation of ketolide: application to the solution phase parallel synthesis of N-desosaminyl-substituted ketolides using ion exchange resins

A series of N-desosaminyl-substituted ketolides was synthesized in parallel by reductive amination of various aldehydes by a N-desmethyl-ketolide scaffold followed by a solid phase extraction protocol using ion exchange resins. In addition, we have demonstrated that diethyl azodicarboxylate (DEAD) can be used efficiently as a N-demethylating reagent to access to N-desmethyl-ketolides.