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Indirect enantioresolution of ( R , S )‐mexiletine by reversed‐phase high‐performance liquid chromatography via diastereomerization with [( S , S )‐ O , O '‐di‐ p ‐toluoyl tartaric acid anhydride], ( S )‐naproxen and nine chiral reagents synthesized as variants of Marfey's reagent
Author(s) -
Bhushan R.,
Tanwar Shivani,
Dixit Shuchi
Publication year - 2011
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.1461
Subject(s) - diastereomer , chemistry , detection limit , reagent , chromatography , naproxen , chiral derivatizing agent , stereocenter , tartaric acid , high performance liquid chromatography , organic chemistry , chiral column chromatography , enantioselective synthesis , catalysis , medicine , alternative medicine , pathology , citric acid
Eleven chiral derivatizing reagents (CDRs) were used for preparation of diastereomers of ( R , S )‐mexiletine containing a primary amino group in close proximity to the stereogenic center. One anhydride, namely [( S , S )‐ O , O '‐di ‐p ‐toluoyl tartaric acid anhydride] was synthesized and ( S )‐naproxen was used as such as the chiral derivatizing reagent. The other nine CDRs were synthesized by substituting one of the fluorine atoms in 1,5‐difluoro‐2,4‐dinitrobenzene with six amino acid amides and three amino acids. The diastereomers were separated by reversed‐phase high‐performance liquid chromatography. The method was validated for linearity, accuracy, limit of detection and limit of quantification. The limit of detection was found in the range of 10–30 pmol. Copyright © 2010 John Wiley & Sons, Ltd.