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( 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
Author(s) -
Bhushan Ravi,
Lal Manohar
Publication year - 2012
Publication title -
biomedical chromatography
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.4
H-Index - 65
eISSN - 1099-0801
pISSN - 0269-3879
DOI - 10.1002/bmc.2735
Subject(s) - chemistry , diastereomer , reagent , chromatography , trifluoroacetic acid , chiral derivatizing agent , hydrazone , detection limit , hydrazine (antidepressant) , high performance liquid chromatography , organic chemistry , chiral column chromatography
( 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. Copyright © 2012 John Wiley & Sons, Ltd.