Separation of enantiomers of Baclofen

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dc.contributor.advisorCaira, Mino Ren_ZA
dc.contributor.authorWildervanck, Alexander Franciscusen_ZA
dc.date.accessioned2016-07-19T14:23:16Z
dc.date.available2016-07-19T14:23:16Z
dc.date.issued1996en_ZA
dc.description.abstract(3-(Aminomethyl)-4-chlorobenzenepropanoic acid (Baclofen), 3-(p-chlorophenyl)pyrrolidone (Baclofen lactam) and 3-(p-Chlorophenyl)glutaramide (baclofen's synthetic precursor) were individually used as substrates in co-crystallisation experiments with several resolving agents. Experiments were conducted in the solid state and in solution. The (-) enantiomer of the lactam and the ( +) enantiomer of the glutaramide were found to cocrystallise selectively with (2R,3R)-( +)-tartaric acid and (S)-(-)-a.-Methylbenzylamine respectively. Both these dissociable diastereomers Vere analysed by X-ray crystallography. HPLC analysis of the lactam retrieved from the former co-crystals indicated only partial separation of its (+) and (-) enantiomers. X-ray crystallographic, thermal, and polarimetric analyses were perfom1ed on the ( + )- and (-)-salts of the latter co-crystals. The solubilities of these salts in methanol were found to differ by a factor of 4. A solubility diagram was established showing the phase equilibria of various ratios of these two salts in methanol. The(+) enantiomer of the glutaramide was separated from the methylbenzylamine in the (+) salt by treatment with HCI. This enantiomer was converted to (R)-(-)-Baclofen by means of a Hofinann Rearrangement with an overall yield of 40%. The enantiomeric excess of (R)-(".")-Baclofen was 99.7%.en_ZA
dc.identifier.apacitationWildervanck, A. F. (1996). <i>Separation of enantiomers of Baclofen</i>. (Thesis). University of Cape Town ,Faculty of Science ,Department of Chemistry. Retrieved from http://hdl.handle.net/11427/20462en_ZA
dc.identifier.chicagocitationWildervanck, Alexander Franciscus. <i>"Separation of enantiomers of Baclofen."</i> Thesis., University of Cape Town ,Faculty of Science ,Department of Chemistry, 1996. http://hdl.handle.net/11427/20462en_ZA
dc.identifier.citationWildervanck, A. 1996. Separation of enantiomers of Baclofen. University of Cape Town.en_ZA
dc.identifier.ris TY - Thesis / Dissertation AU - Wildervanck, Alexander Franciscus AB - (3-(Aminomethyl)-4-chlorobenzenepropanoic acid (Baclofen), 3-(p-chlorophenyl)pyrrolidone (Baclofen lactam) and 3-(p-Chlorophenyl)glutaramide (baclofen's synthetic precursor) were individually used as substrates in co-crystallisation experiments with several resolving agents. Experiments were conducted in the solid state and in solution. The (-) enantiomer of the lactam and the ( +) enantiomer of the glutaramide were found to cocrystallise selectively with (2R,3R)-( +)-tartaric acid and (S)-(-)-a.-Methylbenzylamine respectively. Both these dissociable diastereomers Vere analysed by X-ray crystallography. HPLC analysis of the lactam retrieved from the former co-crystals indicated only partial separation of its (+) and (-) enantiomers. X-ray crystallographic, thermal, and polarimetric analyses were perfom1ed on the ( + )- and (-)-salts of the latter co-crystals. The solubilities of these salts in methanol were found to differ by a factor of 4. A solubility diagram was established showing the phase equilibria of various ratios of these two salts in methanol. The(+) enantiomer of the glutaramide was separated from the methylbenzylamine in the (+) salt by treatment with HCI. This enantiomer was converted to (R)-(-)-Baclofen by means of a Hofinann Rearrangement with an overall yield of 40%. The enantiomeric excess of (R)-(".")-Baclofen was 99.7%. DA - 1996 DB - OpenUCT DP - University of Cape Town LK - https://open.uct.ac.za PB - University of Cape Town PY - 1996 T1 - Separation of enantiomers of Baclofen TI - Separation of enantiomers of Baclofen UR - http://hdl.handle.net/11427/20462 ER - en_ZA
dc.identifier.urihttp://hdl.handle.net/11427/20462
dc.identifier.vancouvercitationWildervanck AF. Separation of enantiomers of Baclofen. [Thesis]. University of Cape Town ,Faculty of Science ,Department of Chemistry, 1996 [cited yyyy month dd]. Available from: http://hdl.handle.net/11427/20462en_ZA
dc.language.isoengen_ZA
dc.publisher.departmentDepartment of Chemistryen_ZA
dc.publisher.facultyFaculty of Scienceen_ZA
dc.publisher.institutionUniversity of Cape Town
dc.subject.otherChemistryen_ZA
dc.titleSeparation of enantiomers of Baclofenen_ZA
dc.typeMaster Thesis
dc.type.qualificationlevelMasters
dc.type.qualificationnameMScen_ZA
uct.type.filetypeText
uct.type.filetypeImage
uct.type.publicationResearchen_ZA
uct.type.resourceThesisen_ZA
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