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Chemistry of Heterocyclic Compounds

, Volume 30, Issue 6, pp 724–728 | Cite as

Synthesis ofα-substitutedα-amino acids by the alkylation of 5-oxazolinone derivatives

  • V. A. Slavinskaya
  • D. É. Sile
  • M. Yu. Katkevich
  • É. Kh. Korchagova
  • É. Lukevits
Article

Abstract

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 ofα-methyl-phenylalanine,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- oxazolinone with ethyl iodide gave a dimer namely, 3-(benzoylamino)-3,5-dibenzylpyrrolidine-2,4-dione.

Keywords

Methyl Ester Ethyl Organic Chemistry Iodide 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1995

Authors and Affiliations

  • V. A. Slavinskaya
  • D. É. Sile
  • M. Yu. Katkevich
  • É. Kh. Korchagova
  • É. Lukevits

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