Rarely does the literature describe the synthesis of esters from amides. I understand that amides are a relatively unreactive functional group but they can easily be hydrolysed to give carboxylic acids under basic or acid conditions. Why can't they be converted to methyl esters under similar conditions using methanol in place of water?
Surely the mechanism would be identical to hydrolysis? Additionally, the pKa of water is very similar to methanol so I cannot justify it on the basis of nucleophilicity/basicity. The only thing I can think of is steric hindrance but methanol isn't that bulky compared to water.