Premium
Microchemical enantioseparation of betaxolol and orciprenaline by reversed phase HPLC
Author(s) -
Nagar Hariom,
Vyas Renu,
Bhushan Ravi
Publication year - 2020
Publication title -
separation science plus
Language(s) - English
Resource type - Journals
ISSN - 2573-1815
DOI - 10.1002/sscp.202000061
Subject(s) - diastereomer , chemistry , cyanuric chloride , chiral derivatizing agent , chromatography , high performance liquid chromatography , enantiomer , detection limit , moiety , triazine , organic chemistry , chiral column chromatography
Enantioseparation of ( RS )‐orciprenaline and ( RS )‐betaxolol was achieved by synthesizing their diastereomeric derivatives with chiral derivatizing reagents prepared on a cyanuric chloride platform. There were three dichloro‐triazine derivatives with amino acid amides as chiral auxiliaries and three monochloro‐triazine derivatives with methoxy as achiral moiety and amino acid amides as chiral auxiliaries in cyanuric chloride. A total of 12 pairs of diastereomeric derivatives were synthesized under microwave irradiation and were separated using reversed phase high‐performance liquid chromatography by applying different mobile phases on a C 18 column in gradient eluting mode with ultraviolet detection at 230 nm. Resolutions were compared and interpreted on the basis of structure of chiral auxiliaries. Besides, diastereomeric derivatives were separated by open column chromatography and the samples so obtained were used for confirmation of their elution order and configuration by 1 H‐NMR spectroscopy. In addition, lowest energy optimized structures of diastereomeric derivatives were developed using the density functional theory based Gaussian software that were interpreted to supplement the absolute configurations. The method validation was carried out for detection limit, linearity, accuracy, and precision. Limits of detection were 0.005 and 0.007 µg/mL.