Sciencemadness Discussion Board

N-Arylation of Amino acids

DrGandham - 29-3-2019 at 23:01

Hello there,

I am working on N-Arylation of alpha amino acids and peptide coupling to synthesize a molecule. Could any body suggest me how to minimize the racemization of amino acid(ester) during N-arylation and peptide coupling. I am trying both traditional (thermal) and Buckwald coupling for N-arylation.

Metacelsus - 30-3-2019 at 00:23

Racemization involves deprotonation at the alpha carbon. The racemization rate is thus a function of pH (and of course temperature). You should try to avoid strong bases and high temperatures.