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


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.


Methyl Ester Ethyl Organic Chemistry Iodide 
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  1. 1.
    G. I. Chipens, L. K. Polevaya, N. I. Veretenikova, and A. Yu. Krikis, Structure and Functions of Low-Molecular-Weight Peptides [in Russian], Zinatne, Riga (1980).Google Scholar
  2. 2.
    G. I. Chipens, V. A. Slavinskaya, A. K. Strautinya, D. É. Sile, D. R. Kreile, and A. Yu. Krikis, Modified Amino Acids and Related Peptides [in Russian], Zinatne, Riga (1987), p. 35.Google Scholar
  3. 3.
    C. Robinson, Med. Actualities,16, 343 (1980).Google Scholar
  4. 4.
    R. N. Brogden, R. C. Heel, T. M. Speight, and G. S. Avery, Drugs,21, 81 (1981).Google Scholar
  5. 5.
    G. C. Barret, Amino Acids, Peptides, Proteins, No. 12, 1 (1981).Google Scholar
  6. 6.
    D Seebach, T. Gees, and F. Schuler, Ann., No. 7, 785 (1993).Google Scholar
  7. 7.
    B. Kübel, P. Gruber, R. Hurnaus, and W. Steglich, Chem. Ber.,112, 128 (1979).Google Scholar
  8. 8.
    M. T. Leplawy, D. S. Jones, G. W. Kenner, and R. C. Sheppard, Tetrahedron,11, 39 (1960).Google Scholar
  9. 9.
    L. D. Taylor, T. E. Platt. and M. N. Mach, Polym. Lett., No. 8, 537 (1970).).Google Scholar
  10. 10.
    Organic Synthesis [Russian translation], Vol. 2, Inos. Lett., Moscow (1949) . p. 150.Google Scholar
  11. 11.
    A. S. Gudkova, G. M. Oustapchuk, I. V. Petrosyan, and O. A. Reutov. Dokl. Akad. Nauk SSSR,194, 1086 (1970).Google Scholar
  12. 12.
    Yu. N. Belokon', N. I. Chernoglazova, K. A. Kuchetkov (Kochetkow), N. S. Garbalinskaya, and V. M. Belikov, J. Chem. Soc., Chem. Commun., No. 3. 171 (1985).Google Scholar
  13. 13.
    J. F. Tilney-Bassett and W A. Waters, J. Chem. Soc., No. 10, 3129(1957).Google Scholar

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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