The optical resolution of albuterol

 

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dc.contributor.advisor Caira, Mino R en_ZA
dc.contributor.advisor Hunter, Roger en_ZA
dc.contributor.advisor Nassimbeni, Luigi R en_ZA
dc.contributor.author Stevens, Anne Theresa en_ZA
dc.date.accessioned 2016-05-13T09:35:28Z
dc.date.available 2016-05-13T09:35:28Z
dc.date.issued 1998 en_ZA
dc.identifier.citation Stevens, A. 1998. The optical resolution of albuterol. University of Cape Town. en_ZA
dc.identifier.uri http://hdl.handle.net/11427/19648
dc.description.abstract 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. en_ZA
dc.language.iso eng en_ZA
dc.subject.other Chemistry en_ZA
dc.title The optical resolution of albuterol en_ZA
dc.type Thesis / Dissertation en_ZA
uct.type.publication Research en_ZA
uct.type.resource Thesis en_ZA
dc.publisher.institution University of Cape Town
dc.publisher.faculty Faculty of Science en_ZA
dc.publisher.department Department of Chemistry en_ZA
dc.type.qualificationlevel Masters en_ZA
dc.type.qualificationname MSc en_ZA
uct.type.filetype Text
uct.type.filetype Image


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