Highly efficient resolutions of 1,4-benzodioxane-2-carboxylic acid with para substituted 1-phenylethylamines |
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| Institution: | 1. Cardiff School of Pharmacy and Pharmaceutical Sciences, Cardiff, King Edward VII Avenue, Cardiff, CF103NB, UK;2. Rega Institute for Medical Research, University of Leuven, Belgium;3. Department of Chemistry & Biochemistry, University of Wisconsin- Milwaukee, Milwaukee, WI 53211, USA;1. Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, Via Mangiagalli 25, 20133 Milano, Italy;2. Dipartimento di Scienze Biomediche Chirurgiche e Odontoiatriche, Università degli Studi di Milano, Via C. Pascal 36, 20133 Milano, Italy;3. Dipartimento di Scienze Farmacologiche e Biomolecolari—DiSFeb, Università degli Studi di Milano, via C. Pascal 36, 20133 Milano, Italy;4. Dipartimento di Farmacia, Università di Genova, Viale Benedetto XV 3, 16132 Genova, Italy;1. Dienstleistungszentrum Ländlicher Raum (DLR) Rheinpfalz, Institute for Viticulture and Oenology, Breitenweg 71, D-67435 Neustadt an der Weinstraße, Germany;2. University Duisburg-Essen, Faculty for Chemistry, Instrumental Analytical Chemistry, Universitätsstraße 5, D-45141 Essen, Germany;3. Mannheim University of Applied Sciences, Faculty of Biotechnology, Paul-Wittsack-Str. 10, D-68163 Mannheim, Germany;1. Master''s Degree Program in Pharmaceutical Science, Department of Pharmaceutical Sciences, Faculty of Pharmacy, Chiang Mai University, Chiang Mai, Thailand;2. Laboratory of Physical Chemistry, Molecular and Cellular Biology, Department of Radiologic Technology, Faculty of Associated Medical Sciences, Chiang Mai University, Chiang Mai, Thailand;3. Department of Pharmaceutical Sciences, Faculty of Pharmacy, Chiang Mai University, Chiang Mai, Thailand;4. Research Center of Pharmaceutical Nanotechnology, Chiang Mai University, Chiang Mai, Thailand |
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| Abstract: | The salts of (S)- and (R)-1,4-benzodioxane-2-carboxylic acid with eight (S)-1-arylethylamines were prepared. The determination of their melting points and of their solubilities in alcohol solvents revealed large differences between the diastereomeric benzodioxanecarboxylates of (S)-1-(p-nitrophenyl)ethylamine and of (S)-1-(p-methylphenyl)ethylamine. Therefore, these latter amines were selected to resolve (±)-1,4-benzodioxane-2-carboxylic acid by diastereoselective crystallization finding that both of them display a very high resolution ability for such a substrate, which contrasts with the null efficiency of unsubstituted 1-phenylethylamine. These results are consistent with DSC evidences, which indicated that the two successfully resolved diastereomeric systems are binary mixtures exhibiting a eutectic with a high content of the more soluble diastereomeric salt. The new procedures can advantageously replace the two resolutions we had previously reported, that of the same acid with dehydroabietylamine and that of glycerol acetonide, a precursor of 1,4-benzodioxane-2-carboxylic acid, with 1-phenylethylamine. |
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