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An Enantioselective...
An Enantioselective Hydrogenation of an Alkenoic Acid as a Key Step in the Synthesis of AZD2716
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- Karlsson, Staffan (författare)
- AstraZeneca, Sweden
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- Sörensen, Henrik (författare)
- AstraZeneca, Sweden
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- Andersen, Sören M. (författare)
- AstraZeneca, Sweden
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- Cruz, Angele (författare)
- AstraZeneca, Sweden
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- Ryberg, Per (författare)
- RISE,SP Process Development
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(creator_code:org_t)
- 2016-01-07
- 2016
- Engelska.
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Ingår i: Organic Process Research & Development. - : American Chemical Society (ACS). - 1083-6160 .- 1520-586X. ; 20:2, s. 262-269
- Relaterad länk:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Ämnesord
Stäng
- 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.
Ämnesord
- MEDICIN OCH HÄLSOVETENSKAP -- Medicinska och farmaceutiska grundvetenskaper -- Läkemedelskemi (hsv//swe)
- MEDICAL AND HEALTH SCIENCES -- Basic Medicine -- Medicinal Chemistry (hsv//eng)
Nyckelord
- Carboxylic acids
- Rhodium
- Active pharmaceutical ingredients
- Asymmetric hydrogenation
- Basic hydrolysis
- Enantioselective hydrogenation
- Rhodium-catalyzed
- Ruthenium based catalysts
- Suzuki couplings
- Unsaturated carboxylic acids
- Hydrogenation
Publikations- och innehållstyp
- ref (ämneskategori)
- art (ämneskategori)
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