Achiral derivatization as a means of improving the chromatographic resolution of racemic alcohols on benzoylcellulose CSPs
✍ Scribed by Eric Francotte
- Publisher
- John Wiley and Sons
- Year
- 1998
- Tongue
- English
- Weight
- 162 KB
- Volume
- 10
- Category
- Article
- ISSN
- 0899-0042
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✦ Synopsis
The advantages that can be gained from derivatization of various racemic aliphatic and aromatic alcohols prior to enantiomeric chromatographic separation have been systematically investigated for a series of benzoate derivatives. Three cellulose-based CSPs available in the pure polymeric form-tribenzoyl cellulose (TBC), metamethylbenzoyl cellulose (MMBC), and para-methylbenzoyl cellulose (PMBC)-were selected and several benzoate derivatives varying in the nature and the position of the substituent on the benzoyl group were prepared and analysed. TBC clearly gives the broadest application range, and among the different benzoate esters the best selectivity was generally obtained with either the 4-methoxybenzoate or the 4-methylbenzoate derivatives. Based on these results, some empirical rules could be formulated for optimizing the enantiomeric separation of racemic alcohols, which make up one of the most important classes of chemical substances used as drugs and biocides, or as building blocks for their synthesis. An application of this approach to the preparative separation of the enantiomers of a drug intermediate is also shown.