A relatively simple question. We want to make a derivatised Fmoc-histidine
and are starting by taking L-histidine and methylating the carboxy group to
protect it. I have used refluxing in HCl and methonol previously to do
this, but have recently heard that this could lead to racemisation. I
could imagine this is a problem in the workup where the product is basified
and extracted, but am not aware of racemisation during the reflux itself.
Can anyone clarify whether there is a problem here (we are not using dry
HCl gas as suggested in Bodanszky and Bodanszky.) Thanks for your help.
Colin Barrow
University of Melbourne
Australia