title: (S)-Naproxen as a platform to develop chiral derivatizing reagent for reversed-phase high-performance liquid chromatographic enantioseparation of analytes having a carbonyl functional group.
abstract: (S)-Naproxen was used to synthesize a chiral reagent, (S)-2-(6-methoxynaphthalen-2-yl)propanehydrazide, by itsreaction with hydrazine hydrate in the presence of dicyclohexylcarbodiimide as coupling agent. The reagent was characterized and its chiral purity was established. It was used as a chiral derivatizing reagent for the synthesis of hydrazone diastereomers, under microwave irradiation, of certain chiral aldehydes and ketones. The respective diastereomers were separated by reversed-phase high-performance liquid chromatography using a binary solvent combination containing trifluoroacetic acid. The diastereomers were detected at 231 nm. The method was validated for accuracy, precision, and limit of detection (LOD). For a series of hydrazones the LOD was found to be in the range 1.62-1.65 pmol/mL.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee 247667, India. rbushfcy@iitr.ernet.in
authors.forename: Ravi
authors.initials: R
authors.lastname: Bhushan
authors.forename: Manohar
authors.initials: M
authors.lastname: Lal
mesh_terms: D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation / Q000379:methods*; D056148:Chromatography, Reverse-Phase / Q000295:instrumentation / Q000379:methods*; D004024:Dicyclohexylcarbodiimide / Q000737:chemistry; D004355:Drug Stability; D006834:Hydrazines / Q000737:chemistry; D057230:Limit of Detection; D016014:Linear Models; D009288:Naproxen / Q000031:analogs & derivatives / Q000737:chemistry*; D015203:Reproducibility of Results; D013237:Stereoisomerism
chemical_list: D006834:Hydrazines; C029424:hydrazine; D004024:Dicyclohexylcarbodiimide; D009288:Naproxen