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

Two β-adrenergic blocking agents, 1-[(1-methylethyl)amino]-3-phenoxy-2-propanol (1) and 1-[(1-methylethyl)amino]-3-(3-methylphenoxy)-2-propanol (2; Toliprolol), were enantioseparated by pH-zone-refining countercurrent chromatography. A two-phase solvent system composed of chloroform containing 0.10 mol/L of di-n-hexyl l-tartrate/0.10 mol/L of boric acid aqueous solution (1:1, v/v) was selected, in which 20 mmol/L triethylamine was added in the organic phase as a retainer and 2 mmol/L HCl was added in the aqueous phase as an eluter. Fifty milligrams of each racemate was completely enantioseparated by pH-zone-refining countercurrent chromatography to yield each enantiomer with a purity of more than 98%, and the recovery of each separated enantiomer reached around 76-82%.

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