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Separation of enantiomers of Baclofen
(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 conduct...
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| Format: | Thesis |
| Language: | English |
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Department of Chemistry
2016
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| _version_ | 1867613359443017728 |
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| access_status_str | Open Access |
| author | Wildervanck, Alexander Franciscus |
| author2 | Caira, Mino R |
| author_browse | Caira, Mino R Wildervanck, Alexander Franciscus |
| author_facet | Caira, Mino R Wildervanck, Alexander Franciscus |
| author_sort | Wildervanck, Alexander Franciscus |
| collection | Thesis |
| description | (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%. |
| format | Thesis |
| id | oai:open.uct.ac.za:11427/20462 |
| institution | University of Cape Town (South Africa) |
| language | eng |
| last_indexed | 2026-06-10T12:34:53.878Z |
| license_str | Not specified — see source repository |
| provenance_str_mv | Harvested via OAI-PMH from UCTD — University of Cape Town Open Access Repository |
| publishDate | 2016 |
| publishDateRange | 2016 |
| publishDateSort | 2016 |
| publisher | Department of Chemistry |
| publisherStr | Department of Chemistry |
| record_format | dspace |
| source_str | UCTD — University of Cape Town Open Access Repository |
| spelling | oai:open.uct.ac.za:11427/20462 Separation of enantiomers of Baclofen Wildervanck, Alexander Franciscus Caira, Mino R Chemistry (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%. 2016-07-19T14:23:16Z 2016-07-19T14:23:16Z 1996 Master Thesis Masters MSc http://hdl.handle.net/11427/20462 eng application/pdf Department of Chemistry Faculty of Science University of Cape Town |
| spellingShingle | Chemistry Wildervanck, Alexander Franciscus Separation of enantiomers of Baclofen |
| thesis_degree_str | Master's |
| title | Separation of enantiomers of Baclofen |
| title_full | Separation of enantiomers of Baclofen |
| title_fullStr | Separation of enantiomers of Baclofen |
| title_full_unstemmed | Separation of enantiomers of Baclofen |
| title_short | Separation of enantiomers of Baclofen |
| title_sort | separation of enantiomers of baclofen |
| topic | Chemistry |
| url | http://hdl.handle.net/11427/20462 |
| work_keys_str_mv | AT wildervanckalexanderfranciscus separationofenantiomersofbaclofen |