The effect of SDE on the separation of diastereomeric salts: a case study for the resolution of mandelic acid derivatives with Pregabalin |
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| Institution: | 1. Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary;2. Research Group for Organic Chemical Technology, Hungarian Academy of Sciences, 1521 Budapest, Hungary;1. Institute of General and Ecological Chemistry, Department of Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Łódź, Poland;2. Polpharma SA Pharmacutical Works, Pelplińska 19, 83-200 Starogard Gdański, Poland;1. Department of Chemistry, University of Missouri-Columbia, 601 S. College Avenue, Columbia, Missouri 65211;2. James L. Winkle College of Pharmacy, University of Cincinnati, 231 Albert Sabin Way, Medical Science Building #3109C, Ohio 45267-0514;1. Department of Chemistry ‘U. Schiff’, University of Florence, Via della Lastruccia 13, I-50019 Sesto Fiorentino, Italy;2. Department of Biomedical, Experimental and Clinical Sciences “Mario Serio”, University of Florence, Viale Morgagni 50, I-50134 Florence, Italy;1. Department of Chemistry, Department of Biomedical and Chemical Engineering, Syracuse University, Syracuse, NY 13244-4100, United States;2. State University of New York College of Environmental Science and Forestry SUNY-ESF, 1 Forestry Drive, Syracuse, NY 13210, United States;3. Department of Biochemistry and Molecular Biology, State University of New York Upstate Medical University, Syracuse, NY 13210, United States;1. Department of Mechanical Engineering, Materials Technology Institute, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven, The Netherlands;2. Dutch Polymer Institute (DPI), P.O. Box 902, 5600 AX Eindhoven, The Netherlands;3. Dipartimento di Chimica Materiali e Ingegneria Chimica G. Natta, Politecnico di Milano, piazza Leonardo da Vinci 32, 20133 Milano, Italy;4. Department of Chemistry and Industrial Chemistry, University of Genova, Via Dodecaneso 31, Genova, Italy |
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| Abstract: | A resolution method has been elaborated for mandelic acid and 2-chloromandelic acid applying the (R)-(−)-3-(aminomethyl)-5-methylhexanoic acid (Pregabalin) as the resolving agent. The formation of the corresponding diastereomers was kinetically controlled. This observation was rationalized by the behavior of enantiomeric mixtures of mandelic acid, 2-chloromandelic acid, and 3-(aminomethyl)-5-methylhexanoic acid. It was found that the eutectic composition of Pregabalin influenced the diastereomeric excess of the diastereomers formed under kinetic control. |
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