The determination of enantiomer composition of 1‐((3‐chlorophenyl)‐(phenyl)methyl) amine and 1‐((3‐chlorophenyl)(phenyl)‐methyl) urea (galodif) by nmr spectroscopy, chiral hplc, and polarimetry

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Abstract

For the first time, a method for enantiomer resolution of the anticonvulsant Galodif (1‐((3‐chlorophenyl)(phenyl)methyl) urea) by chiral HPLC was developed, whereas the enantiomeric composition of 1‐((3‐chlorophenyl)(phenyl) methyl) amine—precursor in Galodif synthesis—cannot be resolved by this method. However, starting 1‐((3‐chlorophenyl)(phenyl)methyl) amine quantitatively forms diastereomeric N‐((3‐chlorophenyl)(phenyl)methyl)‐1‐ camphorsulfonamides in reaction with chiral (1R)‐(+)‐ or (1S)‐(−)‐camphor‐10‐ sulfonyl chlorides. The diastereomeric ratio of obtained camphorsulfonamides can be easily determined by NMR1H and13C spectroscopy. The DFT calculations of specific rotation of Galodif enantiomers showed good agreement with experimental data. The absolute configuration of enantiomers was proposed for the first time.

Original languageEnglish
Pages (from-to)1135-1143
Number of pages9
JournalChirality
Volume30
Issue number10
DOIs
Publication statusPublished - 2018

Keywords

  • Anticonvulsants
  • Chiral analysis
  • Chiral HPLC
  • Galodif
  • NMR spectroscopy
  • Polarimetry
  • Specific rotation calculations

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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