Chemoenzymatic Protocol for the Synthesis of Enantiopure β-Blocker (S)-Bisoprolol
The β-blocker (S)-bisoprolol hemifumarate has been synthesised in 96% enantiomeric excess with 19% total yield in a six-step synthesis. A transesterification reaction of the racemic chlorohydrin 1-chloro-3-(4-((2-isopropoxyethoxy)methyl)phenoxy)propan-2-ol catalysed by lipase B from Candida antarcti...
| Published in: | Catalysts |
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| Main Authors: | , |
| Format: | Text |
| Language: | English |
| Published: |
Multidisciplinary Digital Publishing Institute
2022
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| Subjects: | |
| Online Access: | https://doi.org/10.3390/catal13010054 |
| _version_ | 1821749691809792000 |
|---|---|
| author | Lucas Bocquin Elisabeth Egholm Jacobsen |
| author_facet | Lucas Bocquin Elisabeth Egholm Jacobsen |
| author_sort | Lucas Bocquin |
| collection | MDPI Open Access Publishing |
| container_issue | 1 |
| container_start_page | 54 |
| container_title | Catalysts |
| container_volume | 13 |
| description | The β-blocker (S)-bisoprolol hemifumarate has been synthesised in 96% enantiomeric excess with 19% total yield in a six-step synthesis. A transesterification reaction of the racemic chlorohydrin 1-chloro-3-(4-((2-isopropoxyethoxy)methyl)phenoxy)propan-2-ol catalysed by lipase B from Candida antarctica resulted in the R-chlorohydrin in high enantiomeric purity. Reaction of this building block with isopropylamine in methanol gave (S)-bisoprolol, and further reaction with fumaric acid gave (S)-bisoprolol fumarate in 96% ee. Specific rotation value confirmed the absolute configuration of the enantiopure drug. |
| format | Text |
| genre | Antarc* Antarctica |
| genre_facet | Antarc* Antarctica |
| id | ftmdpi:oai:mdpi.com:/2073-4344/13/1/54/ |
| institution | Open Polar |
| language | English |
| op_collection_id | ftmdpi |
| op_doi | https://doi.org/10.3390/catal13010054 |
| op_relation | Biocatalysis https://dx.doi.org/10.3390/catal13010054 |
| op_rights | https://creativecommons.org/licenses/by/4.0/ |
| op_source | Catalysts; Volume 13; Issue 1; Pages: 54 |
| publishDate | 2022 |
| publisher | Multidisciplinary Digital Publishing Institute |
| record_format | openpolar |
| spelling | ftmdpi:oai:mdpi.com:/2073-4344/13/1/54/ 2025-01-16T19:20:40+00:00 Chemoenzymatic Protocol for the Synthesis of Enantiopure β-Blocker (S)-Bisoprolol Lucas Bocquin Elisabeth Egholm Jacobsen 2022-12-27 application/pdf https://doi.org/10.3390/catal13010054 EN eng Multidisciplinary Digital Publishing Institute Biocatalysis https://dx.doi.org/10.3390/catal13010054 https://creativecommons.org/licenses/by/4.0/ Catalysts; Volume 13; Issue 1; Pages: 54 ( S )-bisoprolol enantiopure building blocks Candida antarctica lipase B chiral chromatography Text 2022 ftmdpi https://doi.org/10.3390/catal13010054 2023-08-01T07:59:34Z The β-blocker (S)-bisoprolol hemifumarate has been synthesised in 96% enantiomeric excess with 19% total yield in a six-step synthesis. A transesterification reaction of the racemic chlorohydrin 1-chloro-3-(4-((2-isopropoxyethoxy)methyl)phenoxy)propan-2-ol catalysed by lipase B from Candida antarctica resulted in the R-chlorohydrin in high enantiomeric purity. Reaction of this building block with isopropylamine in methanol gave (S)-bisoprolol, and further reaction with fumaric acid gave (S)-bisoprolol fumarate in 96% ee. Specific rotation value confirmed the absolute configuration of the enantiopure drug. Text Antarc* Antarctica MDPI Open Access Publishing Catalysts 13 1 54 |
| spellingShingle | ( S )-bisoprolol enantiopure building blocks Candida antarctica lipase B chiral chromatography Lucas Bocquin Elisabeth Egholm Jacobsen Chemoenzymatic Protocol for the Synthesis of Enantiopure β-Blocker (S)-Bisoprolol |
| title | Chemoenzymatic Protocol for the Synthesis of Enantiopure β-Blocker (S)-Bisoprolol |
| title_full | Chemoenzymatic Protocol for the Synthesis of Enantiopure β-Blocker (S)-Bisoprolol |
| title_fullStr | Chemoenzymatic Protocol for the Synthesis of Enantiopure β-Blocker (S)-Bisoprolol |
| title_full_unstemmed | Chemoenzymatic Protocol for the Synthesis of Enantiopure β-Blocker (S)-Bisoprolol |
| title_short | Chemoenzymatic Protocol for the Synthesis of Enantiopure β-Blocker (S)-Bisoprolol |
| title_sort | chemoenzymatic protocol for the synthesis of enantiopure β-blocker (s)-bisoprolol |
| topic | ( S )-bisoprolol enantiopure building blocks Candida antarctica lipase B chiral chromatography |
| topic_facet | ( S )-bisoprolol enantiopure building blocks Candida antarctica lipase B chiral chromatography |
| url | https://doi.org/10.3390/catal13010054 |