Analytical and semipreparative high performance liquid chromatography enantioseparation of new substituted 1-thiocarbamoyl-3,5-diaryl-4,5-dihydro-(1H)-pyrazoles on polysaccharide-based chiral stationary phases in normal-phase, polar organic and reversed-phase conditions

J Chromatogr A. 2006 Jan 6;1101(1-2):198-203. doi: 10.1016/j.chroma.2005.10.003. Epub 2005 Oct 24.

Abstract

The direct HPLC enantioseparation of five pairs of new chiral pyrazole derivatives on coated cellulose- and amylose-based chiral stationary phases (Chiralpak AD, Chiralcel OJ and Chiralcel OJ-RH) and new immobilised amylose-based Chiralpak IA CSP was performed. Very high enantioselectivity factor (alpha) values were achieved in polar organic and reversed-phase conditions by using OJ-RH as CSP. Chiralpak IA exhibited an excellent chiral resolving ability in normal-phase mode and it allowed the enantioseparation of analytes investigated with resolution factors (Rs) >20. Due to its bonded nature, it was successfully employed at analytical and semipreparative scale in combination with normal-phase eluents containing "non-standards" solvents such as acetone.

MeSH terms

  • Amylose / analogs & derivatives
  • Benzoates
  • Cellulose / analogs & derivatives
  • Chromatography, High Pressure Liquid / instrumentation
  • Chromatography, High Pressure Liquid / methods*
  • Phenylcarbamates
  • Pyrazoles / isolation & purification*
  • Solvents
  • Stereoisomerism

Substances

  • Benzoates
  • Phenylcarbamates
  • Pyrazoles
  • Solvents
  • tris(4-methylbenzoate)cellulose
  • Chiralpak AD
  • Cellulose
  • Amylose