Preparation of a New Chiral Stationary Phase Based on Macrocyclic Amide Chiral Selector for the Liquid Chromatographic Chiral Separations

Chirality. 2016 Mar;28(3):253-8. doi: 10.1002/chir.22569. Epub 2016 Jan 4.

Abstract

A new chiral stationary phase (CSP) based on macrocyclic amide receptor was prepared starting from (1R,2R)-1,2-diphenylethylenediamine. The new CSP was successfully applied to the resolution of various N-(substituted benzoyl)-α-amino amides with reasonably good separation factors and resolutions (α = 1.75 ~ 2.97 and RS = 2.89 ~ 6.82 for 16 analytes). The new CSP was also applied to the resolution of 3-substituted 1,4-benzodiazepin-2-ones and some diuretic chiral drugs including bendroflumethiazide and methylchlothiazide and metolazone. The resolution results for 3-substituted 1,4-benzodiazepin-2-ones and some diuretic chiral drugs were also reasonably good.

Keywords: chiral stationary phase; enantiomer separation; liquid chromatography; macrocyclic amide chiral selector.