Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
An Enantioselective Hydrogenation of an Alkenoic Acid as a Key Step in the Synthesis of AZD2716
Show others and affiliations
2016 (English)In: Organic Process Research & Development, ISSN 1083-6160, E-ISSN 1520-586X, Vol. 20, no 2, 262-269 p.Article in journal (Refereed) Published
Abstract [en]

A classical resolution of a racemic carboxylic acid through salt formation and an asymmetric hydrogenation of an α,β-unsaturated carboxylic acid were investigated in parallel to prepare an enantiomerically pure alkanoic acid used as a key intermediate in the synthesis of an antiplaque candidate drug. After an extensive screening of rhodium- and ruthenium-based catalysts, we developed a rhodium-catalyzed hydrogenation that gave the alkanoic acid with 90% ee, and after a subsequent crystallization with (R)-1-phenylethanamine, the ee was enriched to 97%. The chiral acid was then used in sequential Negishi and Suzuki couplings followed by basic hydrolysis of a nitrile to an amide to give the active pharmaceutical ingredient in 22% overall yield. © 2016 American Chemical Society.

Place, publisher, year, edition, pages
2016. Vol. 20, no 2, 262-269 p.
Keyword [en]
Carboxylic acids, Rhodium, Active pharmaceutical ingredients, Asymmetric hydrogenation, Basic hydrolysis, Enantioselective hydrogenation, Rhodium-catalyzed, Ruthenium based catalysts, Suzuki couplings, Unsaturated carboxylic acids, Hydrogenation
National Category
Medicinal Chemistry
Identifiers
URN: urn:nbn:se:ri:diva-27657DOI: 10.1021/acs.oprd.5b00382OAI: oai:DiVA.org:ri-27657DiVA: diva2:1059475
Available from: 2016-12-22 Created: 2016-12-21 Last updated: 2017-01-29Bibliographically approved

Open Access in DiVA

No full text

Other links

Publisher's full text
By organisation
SP Process Development
In the same journal
Organic Process Research & Development
Medicinal Chemistry

Search outside of DiVA

GoogleGoogle Scholar

Altmetric score

Total: 11 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
v. 2.26.0