Stereoselective separation of β-adrenergic blocking agents containing two chiral centers by countercurrent chromatography

Application of pH‐zone‐refining countercurrent chromatography in the chiral separation of two β‐adrenergic blocking agents

“…Compounds 1 and 2 are ionizable organic base according to their chemical structures. It was found that they could be well enantioseparated by conventional countercurrent chromatography using di-n-hexyl L-tartrate and boric acid as chiral selector, as reported in our recent work [25]. A two-phase solvent system composed of chloroform/0.05 mol/L of acetate buffer containing 0.10 mol/L of boric acid (1:1, v/v) was used, in which 0.10 mol/L of di-n-hexyl L-tartrate was added in the organic phase as a chiral selector.…”

“…Compared with traditional liquid chromatographic techniques, much smaller number of literatures about chiral separation by countercurrent chromatography was available due to its relatively low theoretical plates of separation column [20][21][22][23]. However, in the recent two years, increasing number of papers has been published on preparative enantioseparation by countercurrent chromatography [24][25][26][27][28][29][30][31][32][33]. Unfortunately, only five papers reporting successful chiral separations could be found in the literature when it comes to pH-zone-refining countercurrent chromatography since 1990s [34][35][36][37][38].…”

Chiral separation of β‐blockers by supercritical fluid chromatography using Chiralpak‐IG and Chiralpak IBN‐5 columns

“…It is well-known that in many countries, these medicines are being sold as a racemic mixture, while the racemic form may be toxic or ballast to the patients. [6][7][8][9] These β-blockers have been separated by using various highperformance liquid chromatography (HPLC) methods, [10][11][12][13][14][15][16] but the methods reported in these papers are not eco-friendly, especially the use of toxic chemicals, high run time and a lot of use of manpower consumption. On the other hand, supercritical fluid chromatography (SFC) is a technique of low cost, less run time, higher column efficiency, and eco-friendly mobile phases that are the initial requirement of pharmaceutical industries.…”

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.…”