i was asked to synthesis this compound from this amino acid, i first alkylated the alpha carbon using enolate alkylating method then i esterficated the amino acid but i'm doubtful that my steps are right, do i need to protect the amino group in the esterification step? or even before ? enter image description here

  • $\begingroup$ I don't think your alkene hydration will work on the unprotected amino acid $\endgroup$ – Waylander Oct 18 '20 at 7:45

I think you need a protection strategy and there are several choices. This one uses O'Donnell's benzophenone imine strategy details here.

First you prepare glycine ethyl ester hydrochloride from glycine with EtOH/HCl, a method is here patent.

From the ethyl ester hydrochloride prepare the benzophenone imine by O'Donnell's method as described in ref 1. This gives a protected species that can be easily alkylated under phase-transfer conditions with allyl bromide as described in ref 1

The allyl product is then epoxidised (MCPBA) and the epoxide opened with iodide procedure here

Deprotection with acid hydrolysis gives your target molecule.


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