Separation of diastereoisomers of DuP 105, a novel oxazolidinone antibacterial agent, by supercritical fluid chromatography on a Chiralcel OD column.

Oxazolidinones are a novel class of synthetic, orally-active antibacterial agents. DuP 105, which is representative of this class of compounds, is synthesized as a racemic mixture of two diastereoisomers. To ensure lot-to-lot consistency, separation and quantitation of these diastereoisomers is essential. Separation by reverse phase LC has not been achieved. This paper presents a supercritical fluid chromatography method using a Chiralcel OD column to resolve these diastereoisomers. A retention mechanism is briefly elaborated, based on the effects of temperature, pressure, percent modifier and type of modifier on resolution.