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.

  • $\begingroup$ A google search gave the following reference doi:10.1038/nature14615 which should give you a clearer understanding. $\endgroup$ – user1945827 Feb 28 '17 at 13:30
  • $\begingroup$ Thanks but I've read that paper already and it doesn't answer my question. It just makes the usual statement that amides are unreactive due to resonance stabilisation. If they are so stable why do carboxylic acids readily form but not esters? $\endgroup$ – Alex Feb 28 '17 at 13:58

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