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.
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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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
- Ester Method
- Preparative Method