Open AccessSynthesis of Cyanuric Chloride based Chiral Reagent for RP-HPLC Enantioseparation of (RS)-Propranolol
Author(s) -
Hamza S. Al-Shehri,
Vijay Alwera,
Kiran Chanabasappa Nilugal,
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.2022.23550
Subject(s) - diastereomer , chemistry , cyanuric chloride , reagent , chromatography , chiral derivatizing agent , chloride , high performance liquid chromatography , chlorine , organic chemistry , chiral column chromatography
In this work, four cyanuric chloride based chiral reagents were prepared via nucleophile substitutionof chlorine atom by L-proline derivatives and characterized by UV, FT-IR, HRMS, NMR and elementalanalysis. Racemic propranolol was chosen for the chiral recognition study. The prepared chiral reagentswere used in the synthesis of diastereomeric derivatives of (RS)-propranolol, under microwave heatingconditions. RP-HPLC was used to separate the prepared diastereomeric derivatives. The effect ofvarying eluting phase concentrations and sample concentrations was optimized. The DFT calculationswere performed using Gaussian 09 Rev A.02 to create the lowest energy optimised structures ofdiastereomeric derivatives. LOD (0.324 ng mL-1), LOQ (0.972 ng mL-1), calibration range (0.02-2.0mg mL-1), correlation-coefficient (0.999), and recovery were the validation parameters for the presentmethod (99.09 and 99.81 % for inter-day assay and 98.47 and 99.72 % for intra-day assay).