High-performance liquid chromatographic separation of beta-methyl ADC-13 enolphosphate diphenyl ester and its alpha-methyl diastereomer.
The development of a high-performance liquid chromatographic (HPLC) separation of beta-methyl ADC-13 enolphosphate diphenyl ester, an intermediate compound in the synthesis of a carbapenem antibiotic drug candidate, and its alpha-methyl diastereomer is reported. The method development involved separation on different columns in both normal- and reversed-phase modes. The use of normal-phase mode resulted in the desired elution order of the two diastereomers. The influence of different polar modifiers and their concentrations on resolution, capacity factor and separation factor was investigated. Different stationary phases were compared for their efficiency and resolution. The optimized separation was applied to the determination of the minor diastereomer in the bulk intermediate, and 0.1% minor diastereomer was detectable.
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Analytical Research Department, Merck Research Laboratories, Rahway, NJ 07065-0900, USA.
D000433:1-Propanol / Q000737:chemistry; D000085:Acetates / Q000737:chemistry; D015780:Carbapenems / Q000032:analysis* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D006586:Hexanes / Q000737:chemistry; D010755:Organophosphates / Q000032:analysis* / Q000737:chemistry; D009994:Osmolar Concentration; D013056:Spectrophotometry, Ultraviolet
D000085:Acetates; D015780:Carbapenems; D006586:Hexanes; D010755:Organophosphates; C106035:beta-methyl ADC-13 enolphosphate diphenyl ester; C007650:ethyl acetate; D000433:1-Propanol