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Synthesis of N-p-[di(2-chloroethyl)amino]phenacetylvalylmethionine diastereomers

Conclusions

  1. 1.

    A preparative method has been developed for obtaining diastereomers of N-p-[di(2-chloroethyl)-amino]phenacetylvalylmethionine from enantiomers of N-p-fdi(2-chloroethyl)amino]phenacetylvaline and the corresponding antipodes of methionine benzhydryl ester with the aid of N-ethoxycarbonyl-2-ethoxy-l-2-dihydroquinoline.

  2. 2.

    The synthesis of these diastereomers by the carbodiimide, mixed-anhydride and activated N-hydroxy-piperidyl ester methods is accompanied by appreciable racemization.

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Literature cited

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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2081–2083, September, 1976.

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Klyukene, R.B., Karpavichyus, K.I. & Kil'disheva, O.V. Synthesis of N-p-[di(2-chloroethyl)amino]phenacetylvalylmethionine diastereomers. Russ Chem Bull 25, 1950–1953 (1976). https://doi.org/10.1007/BF00921728

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Keywords

  • Ester
  • Methionine
  • Ester Method
  • Carbodiimide
  • Preparative Method