Open AccessPre-column Derivatization and Separation of Diastereomeric-Derivatives of Racemic Mexiletine and Confirmation of Elution Order and Molecular Configuration
Author(s) -
Tousief Irshad Ahmed,
Vijay Alwera,
V.S. Talismanov,
Nagadeep Jaishetty,
Suman Sehlangia,
Shiv Alwera
Publication year - 2022
Publication title -
asian journal of chemistry/asian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.145
H-Index - 34
eISSN - 0975-427X
pISSN - 0970-7077
DOI - 10.14233/ajchem.2022.23706
Subject(s) - chemistry , mexiletine , diastereomer , cyanuric chloride , enantiomer , elution , chromatography , reagent , enantiomeric excess , derivatization , calibration curve , high performance liquid chromatography , organic chemistry , detection limit , enantioselective synthesis , catalysis , medicine , anesthesia
Present study describes the synthesis of cyanuric chloride based four active chiral reagents (ACRs)and their application in the enantiomeric separation of (RS)-mexiletine. Herein, four cyanuricchloride-based ACRs were prepared by introducing L-proline derivatives under nucleophilic substitutionreaction. The synthesized ACRs were characterized by different spectroscopic techniques. Racemicmexiletine hydrochloride was used for the enantio-recognition study. All the four ACRs were used toconvert (RS)-mexiletine into related diastereomeric derivatives and then separated on the C18-columnof RP-HPLC. The different parameters such as sample amount, the concentration of mobile phase,organic modifier and pump pressure were varied to optimize separation conditions. Theenergy-minimized structures of synthesized diasteromeric derivatives (DDs) were developed usingDFT calculations. The validation study was conducted for the developed method andcorrelation-coefficient, calibration range, LOD and LOQ calculated. The stability and recovery werecalculated by inter and intraday assay.