Add time:09/09/2019         Source:sciencedirect.com

A normal-phase displacement chromatographic method has been developed for the preparative-scale separation of the enantiomers of 1,2-O-dihexadecyl-rac-glycerol-3-O-(3,5-dinitrophenyl)carbamate using the Pirkle-type covalently bonded naphthylalanine silica chiral stationary phase. The separation selectivity of the system has been maximized by varying the tetrahydrofuran concentration and the temperature of the tetrahydrofuran—hexane eluent within the range constrained by the solubility of the sample and the displacer. The 3,5-dinitrobenzoyl ester of n-heptanol, which is more retained under the selected separation conditions than any of the enantiomers of the glycerol ether derivative, was selected and used as displacer in a preparative displacement chromatographic separation of a 20-mg sample of the glycerol ether derivative. For comparison purposes, an analogous overloaded elution mode separation was also completed under identical separation conditions. A large number of product fractions were collected during both the displacement chromatographic run and the corresponding overloaded elution mode run; these were analyzed for enantiomeric purity such that the percent recoveries and the production rates for both separation methods could be calculated.

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