Utility of the Cleavage of Nitrosamides for the Preparation of Chiral Acids after Chromatographie Separation of their Diastereomeric Amides

Franz P. Schmidtchen, Peter Rauschenbach, Helmut Simon

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5 Scopus citations

Abstract

A method for optical resolution of chiral acids is described. It consists of the conversion of racemic acids to diastereomeric amides, their chromatographic separation and subsequent deamidation via the nitrosamide route. Reaction conditions for cleavage of amide derivatives of phenylalanine and methylbenzylamine are given. No or only negligible racemization of carboxylic acids, chiral in a-position takes place under those conditions. The extent of E, Z-isomerization of double bonds is very small, as is the extent of double bond migration from the Zl3-position into conjugation with the carboxyl function. Enantiomerically pure R- or S[2-3H]2-methylbutanoic acid and (-)methyl-3(p-chlorophenyl)-2-chloropropionate (Bidisin®) were prepared by this procedure.

Original languageEnglish
Pages (from-to)98-104
Number of pages7
JournalZeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
Volume32
Issue number1
DOIs
StatePublished - 1 Jan 1977

Keywords

  • Amide Cleavage
  • Nitrosamide
  • Optical Resolution

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