SYNTHESIS OF α-SUBSTITUTED α-AMINO ACIDS BY THE ALKYLATION OF 5-OXAZOLINONE DERIVATIVES

Article abstract of DOI:10.1007/BF01166316

Methods have been developed for the alkylation of 5-oxazolinone derivatives in DMF in the presence of K2CO3, KOH, or diisopropylethylamine and a phase transfer catalyst as well as for the preparation of α-methylphenylalanine, α-methylalanine, α-methylalanine, and the methyl ester of N-benzoyl-α-methylalanine.Increasing the initial concentration of the starting 5-oxazolinone in the reaction mixture leads to a sharp drop in the yield of reaction products due to side condensation reactions.The reaction of 2-phenyl-4-benzyl-5-oxazolinonewith ethyl iodide gave a dimer, mamely, 3-(benzoylamino)-3,5-dibenzylpyrrolidine-2,4-dione.