( 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 | Zendy

Bhushan Ravi | Zendy; Lal Manohar | Zendy

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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.

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