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...

Full description

Bibliographic Details
Published in:Catalysts
Main Authors: Bocquin, Lucas, Jacobsen, Elisabeth Egholm
Format: Article in Journal/Newspaper
Language:English
Published: MDPI 2023
Subjects:
Antarc*
Antarctica
Online Access:https://hdl.handle.net/11250/3098034
https://doi.org/10.3390/catal13010054
id ftntnutrondheimi:oai:ntnuopen.ntnu.no:11250/3098034
record_format openpolar
spelling ftntnutrondheimi:oai:ntnuopen.ntnu.no:11250/3098034 2023-11-12T04:08:04+01:00 Chemoenzymatic Protocol for the Synthesis of Enantiopure β-Blocker (S)-Bisoprolol Bocquin, Lucas Jacobsen, Elisabeth Egholm 2023 application/pdf https://hdl.handle.net/11250/3098034 https://doi.org/10.3390/catal13010054 eng eng MDPI urn:issn:2073-4344 https://hdl.handle.net/11250/3098034 https://doi.org/10.3390/catal13010054 cristin:2131087 Navngivelse 4.0 Internasjonal http://creativecommons.org/licenses/by/4.0/deed.no 13 Catalysts 1 54 Peer reviewed Journal article 2023 ftntnutrondheimi https://doi.org/10.3390/catal13010054 2023-10-25T22:46:39Z 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. publishedVersion Article in Journal/Newspaper Antarc* Antarctica NTNU Open Archive (Norwegian University of Science and Technology) Catalysts 13 1 54
institution Open Polar
collection NTNU Open Archive (Norwegian University of Science and Technology)
op_collection_id ftntnutrondheimi
language English
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. publishedVersion
format Article in Journal/Newspaper
author Bocquin, Lucas
Jacobsen, Elisabeth Egholm
spellingShingle Bocquin, Lucas
Jacobsen, Elisabeth Egholm
Chemoenzymatic Protocol for the Synthesis of Enantiopure β-Blocker (S)-Bisoprolol
author_facet Bocquin, Lucas
Jacobsen, Elisabeth Egholm
author_sort Bocquin, Lucas
title 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_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_sort chemoenzymatic protocol for the synthesis of enantiopure β-blocker (s)-bisoprolol
publisher MDPI
publishDate 2023
url https://hdl.handle.net/11250/3098034
https://doi.org/10.3390/catal13010054
genre Antarc*
Antarctica
genre_facet Antarc*
Antarctica
op_source 13
Catalysts
1
54
op_relation urn:issn:2073-4344
https://hdl.handle.net/11250/3098034
https://doi.org/10.3390/catal13010054
cristin:2131087
op_rights Navngivelse 4.0 Internasjonal
http://creativecommons.org/licenses/by/4.0/deed.no
op_doi https://doi.org/10.3390/catal13010054
container_title Catalysts
container_volume 13
container_issue 1
container_start_page 54
_version_ 1782328485209964544

Similar Items