Question: A clever new method of peptide synthesis involves formation of an amide bond by reaction of an -keto acid with an N-alkyl hydroxylamine: The reaction

A clever new method of peptide synthesis involves formation of an amide bond by reaction of an -keto acid with an N-alkyl hydroxylamine:

The reaction is thought to occur by nucleophilic addition of the N-alkyl hydroxylamine to the keto acid as if forming an oxime (Section 19.8), followed by decarboxylation and elimination of water. Show themechanism.

OH DMF co2 R' H20 R' co2 An a-keto acid A hydroxylamine

OH DMF co2 R' H20 R' co2 An a-keto acid A hydroxylamine An amide

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