Stereoselectiveseparation of racemic trans-paroxol, N-methylparoxetine and paroxetine containing two chiral carbon centres by countercurrent chromatography

Enantioseparation of ondansetron by countercurrent chromatography using sulfobutyl ether‐β‐cyclodextrin as chiral selector

“…Substituted β‐cyclodextrin is one of the most conspicuous and developmental potential chiral selectors due to its special stereoscopic structure and properties [27]. Hydroxypropyl‐β‐cyclodextrin, as the most widely used neutral β‐cyclodextrin, plays an important role in chiral countercurrent chromatography [20,22,23,28–33]. Limited number of literatures reported other substituted β‐cyclodextrins such as hydroxyethyl‐β‐cyclodextrin [21], carboxymethyl‐β‐cyclodextrin [24,34,35], sulfated‐β‐cyclodextrin [36,37], and methyl‐​β‐​cyclodextrin [38].…”

Stereoselective separation of (1S, 4S)‐sertraline from medicinal reaction mixtures by countercurrent chromatography with hydroxypropyl‐β‐cyclodextrin as stereoselective selector

“…Recycling elution mode was usually employed to improve enantioseparation in various chromatographic methods . In our very recent work, CCC was successfully applied for stereoselective separation of drugs and intermediates containing two chiral centers for the first time . In the present work, we want to report our recent work on stereoselective separation of four isomeric sertraline by an analytical countercurrent chromatographic apparatus designed in our lab, ( 1S, 4S ), ( 1R, 4R ), ( 1S, 4R ), and ( 1R, 4S )‐isomer, from the medicinal reaction mixture obtained during the synthesis of the antidepressant drug ( 1S, 4S )‐sertraline hydrochloride.…”

Enantioseparation of acetyltropic acid by countercurrent chromatography with sulfobutyl ether‐β‐cyclodextrin as chiral selector

“…F I G U R E 1 Stereochemical structures of acetyltropic acid enantiomer of studies are available, which are about enantioseparations by CCC [16][17][18][19][20]. To the best of our knowledge, only two papers have been published so far with regard to enantioseparation by CCC using sulfobutyl ether-β-cyclodextrin as chiral selector [26,27], although many papers have been published for enantioseparation by liquid-liquid partition chromatography using hydroxypropyl-β-cyclodextrin and other substituted β-cyclodextrin as chiral selectors [16][17][18][19][20][22][23][24]. At the same time, it is difficult to find a biphasic solvent system along with a chiral selector showing high enantiorecognition toward enantiomer, in which the chiral selector should be predominantly dissolved in only one phase of the biphasic solvent system while the racemate to be enantioseparated can partition freely in both phases.…”

“…CCC is a liquid-liquid partition chromatography that has been widely used for preparative separation of active component from natural product [13], synthetic mixture [14], and fermentation broth [15]. However, only very limited numbers F I G U R E 1 Stereochemical structures of acetyltropic acid enantiomer of studies are available, which are about enantioseparations by CCC [16][17][18][19][20]. The number of theoretical plates of the separation column of CCC being much lower than that of conventional LC makes it difficult to be successfully applied in enantioseparations.…”

“…Thus, numerous novel strategies were used to improve the separation efficiency for enantioseparation by CCC, including modification of chiral selector [21,22], recycling elution mode [23,24] and biphasic recognition [25,26]. To the best of our knowledge, only two papers have been published so far with regard to enantioseparation by CCC using sulfobutyl ether-β-cyclodextrin as chiral selector [26,27], although many papers have been published for enantioseparation by liquid-liquid partition chromatography using hydroxypropyl-β-cyclodextrin and other substituted β-cyclodextrin as chiral selectors [16][17][18][19][20][22][23][24]. In our present work, we want to report our recent research on preparative enantioseparation of racemic acetyltropic acid by CCC using sulfobutyl ether-β-cyclodextrin as chiral selector.…”