Chiral Ionic Liquid that Functions as Both Solvent and Chiral Selector for the Determination of Enantiomeric Compositions of Pharmaceutical Products

Abstract

We have successfully synthesized both enantiomers of a novel chiral ionic liquid, (R)- and (S)-[(3-chloro-2-hydroxypropyl) trimethylammonium][bis((trifluoromethyl)sulfonyl)amide] ((R)- and (S)-[CHTA]+[Tf2N]-) in optically pure form by a simple ion exchange reaction from corresponding chloride salts that are commercially available. In addition to the ease of preparation, this chiral IL has relatively high thermal stability (up to 300 degrees C), is liquid at room temperature (glass transition temperature of -58.4 degrees C), and exhibits strong enantiomeric recognition. The high solubility power and strong enantiomeric recognition ability make it possible to use this chiral IL to solubilize an analyte and to induce diastereomeric interactions for the determination of enantiomeric purity. In fact, we have successfully developed a novel method based on the near-infrared technique with this chiral IL serving both as solvent and as a chiral selector for the determination of enantiomeric purity. Enantiomeric compositions of a variety of pharmaceutical products and amino acids with different shape, size, and functional groups can be sensitively (milligram concentration) and accurately (enantiomeric excess as low as 0.6%) determined by use of this method.