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Asymmetric synthesis of amino acids by the catalytic reduction of azlactones using substituted acylaminoacrylic acids 3. Production of 3,4-dihydroxyphenylalanine

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Conclusions

  1. 1.

    Theα-phenylethylamide of 3-methoxy-4-acetoxyphenylalanine of predominantly SS configuration is obtained in the reaction of the azlactone of 3-methoxy-4-acetoxy-N-acetaminocinnamic acid with S(−)-α-phenylethylamine and hydrogen in the presence of a palladium catalyst in aprotic solvents.

  2. 2.

    The optimal conditions were found for preparing the pure SS diastereomer which yields, upon hydrolysis, optically pure S(−)-3,4-dihydroxyphenylalanine.

  3. 3.

    The methyl esters of N-acetyl-3-methoxy-4-acetoxy- and N-acetyl-3-methoxy-4-hydroxyphenylalanine, predominantly of the R configuration, are obtained in the reduction of the azlactone of 3-methoxy-4-acetoxy- α-acetaminocinnamic acid in methanol in the presence of S(−)-α-phenylethylamine and a palladium catalyst, which indicates the dissymmetrical nature of the catalyst.

  4. 4.

    The reductive aminolysis proceeds mainly by the synchronous reaction of the azlactone with the amine and hydrogen on the catalyst surface.

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Literature cited

  1. 1.

    E. I. Karpeiskaya, L. F. Godunova, E. S. Neupokoeva, and E. I. Klabunovskii, Izv. Akad. Nauk SSSR, Ser. Khim., 1104 (1978).

  2. 2.

    L. F. Godunova, E. I. Karpeiskaya, E. S. Neupokoeva, and E. I. Klabunovskii, Izv. Akad. Nauk SSSR, Ser. Khtm., 1363 (1978).

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    J. Heuben, Methods of Organic Chemistry [Russian translation], 1st ed., Vol. 2, Goskhimizdat (1941), p. 462.

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    West German Patent No. 2,210,938; Chem. Abstr.,77, 165073 (1972).

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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1368–1373, June, 1978.

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Karpeiskaya, E.I., Neupokoeva, E.S., Godunova, L.F. et al. Asymmetric synthesis of amino acids by the catalytic reduction of azlactones using substituted acylaminoacrylic acids 3. Production of 3,4-dihydroxyphenylalanine. Russ Chem Bull 27, 1190–1194 (1978). https://doi.org/10.1007/BF00923374

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Keywords

  • Hydrogen
  • Methyl
  • Methanol
  • Ester
  • Hydrolysis