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The optical resolution of albuterol
The acetonide derivative of (rac)-albuterol has been prepared and used as a substrate in cocrystallisation experiments with several acidic resolving agents~ Successful resolution of the acetonide was achieved with both di-0-benzoyl- and di-0-toluoyltartaric acid, with the (2S,3S)enantiomer of the ac...
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| Format: | Thesis |
| Language: | English |
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Department of Chemistry
2016
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| _version_ | 1867613151985401856 |
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| access_status_str | Open Access |
| author | Stevens, Anne Theresa |
| author2 | Caira, Mino R |
| author_browse | Caira, Mino R Stevens, Anne Theresa |
| author_facet | Caira, Mino R Stevens, Anne Theresa |
| author_sort | Stevens, Anne Theresa |
| collection | Thesis |
| description | The acetonide derivative of (rac)-albuterol has been prepared and used as a substrate in cocrystallisation experiments with several acidic resolving agents~ Successful resolution of the acetonide was achieved with both di-0-benzoyl- and di-0-toluoyltartaric acid, with the (2S,3S)enantiomer of the acid selectively co-crystallising with the desired (R)-albuterol acetonide. High performance liquid chromatography on a chiral stationary phase, and 1H NMR experiments using a chiral shift reagent were used to assess the optical purity of the resolved material. Acid hydrolysis of the resolved acetonide gave rise to the target, (R)-albuterol, which was isolated as an acetate salt. The inferred absolute configuration of the resolved acetonide was assessed by 1H NMR analysis of its (R)-Mosher ester, and confirmed by an X-ray structural determination of its (R)-phenylethylurea derivative. The acetonide derivative of (rac)-albuterol has been prepared and used as a substrate in cocrystallisation experiments with several acidic resolving agents~ Successful resolution of the acetonide was achieved with both di-0-benzoyl- and di-0-toluoyltartaric acid, with the (2S,3S)enantiomer of the acid selectively co-crystallising with the desired (R)-albuterol acetonide. High performance liquid chromatography on a chiral stationary phase, and 1H NMR experiments using a chiral shift reagent were used to assess the optical purity of the resolved material. Acid hydrolysis of the resolved acetonide gave rise to the target, (R)-albuterol, which was isolated as an acetate salt. The inferred absolute configuration of the resolved acetonide was assessed by 1H NMR analysis of its (R)-Mosher ester, and confirmed by an X-ray structural determination of its (R)-phenylethylurea derivative. |
| format | Thesis |
| id | oai:open.uct.ac.za:11427/19648 |
| institution | University of Cape Town (South Africa) |
| language | eng |
| last_indexed | 2026-06-10T12:31:35.974Z |
| 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:11427/19648 The optical resolution of albuterol Stevens, Anne Theresa Caira, Mino R Hunter, Roger Nassimbeni, Luigi R Chemistry The acetonide derivative of (rac)-albuterol has been prepared and used as a substrate in cocrystallisation experiments with several acidic resolving agents~ Successful resolution of the acetonide was achieved with both di-0-benzoyl- and di-0-toluoyltartaric acid, with the (2S,3S)enantiomer of the acid selectively co-crystallising with the desired (R)-albuterol acetonide. High performance liquid chromatography on a chiral stationary phase, and 1H NMR experiments using a chiral shift reagent were used to assess the optical purity of the resolved material. Acid hydrolysis of the resolved acetonide gave rise to the target, (R)-albuterol, which was isolated as an acetate salt. The inferred absolute configuration of the resolved acetonide was assessed by 1H NMR analysis of its (R)-Mosher ester, and confirmed by an X-ray structural determination of its (R)-phenylethylurea derivative. The acetonide derivative of (rac)-albuterol has been prepared and used as a substrate in cocrystallisation experiments with several acidic resolving agents~ Successful resolution of the acetonide was achieved with both di-0-benzoyl- and di-0-toluoyltartaric acid, with the (2S,3S)enantiomer of the acid selectively co-crystallising with the desired (R)-albuterol acetonide. High performance liquid chromatography on a chiral stationary phase, and 1H NMR experiments using a chiral shift reagent were used to assess the optical purity of the resolved material. Acid hydrolysis of the resolved acetonide gave rise to the target, (R)-albuterol, which was isolated as an acetate salt. The inferred absolute configuration of the resolved acetonide was assessed by 1H NMR analysis of its (R)-Mosher ester, and confirmed by an X-ray structural determination of its (R)-phenylethylurea derivative. 2016-05-13T09:35:28Z 2016-05-13T09:35:28Z 1998 Master Thesis Masters MSc http://hdl.handle.net/11427/19648 eng application/pdf Department of Chemistry Faculty of Science University of Cape Town |
| spellingShingle | Chemistry Stevens, Anne Theresa The optical resolution of albuterol |
| thesis_degree_str | Master's |
| title | The optical resolution of albuterol |
| title_full | The optical resolution of albuterol |
| title_fullStr | The optical resolution of albuterol |
| title_full_unstemmed | The optical resolution of albuterol |
| title_short | The optical resolution of albuterol |
| title_sort | optical resolution of albuterol |
| topic | Chemistry |
| url | http://hdl.handle.net/11427/19648 |
| work_keys_str_mv | AT stevensannetheresa theopticalresolutionofalbuterol AT stevensannetheresa opticalresolutionofalbuterol |