Development of a Direct Photocatalytic C–H Fluorination for the Preparative Synthesis of Odanacatib
Late-stage C–H fluorination is an appealing reaction for medicinal chemistry. However, the application of this strategy to process research appears less attractive due to the formation and necessary purification of mixtures of organofluorines. Here we demonstrate that γ-fluoroleucine methyl ester, a...
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| Published in | Organic letters Vol. 17; no. 21; pp. 5200 - 5203 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
American Chemical Society
06.11.2015
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| Subjects | |
| Online Access | Get full text |
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| Abstract | Late-stage C–H fluorination is an appealing reaction for medicinal chemistry. However, the application of this strategy to process research appears less attractive due to the formation and necessary purification of mixtures of organofluorines. Here we demonstrate that γ-fluoroleucine methyl ester, an intermediate critical to the large-scale synthesis of odanacatib, can be accessed directly from leucine methyl ester using a combination of the decatungstate photocatalyst and N-fluorobenzenesulfonimide in flow. This efficient C–H fluorination reaction compares favorably with several generations of classical γ-fluoroleucine process syntheses. |
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| AbstractList | Late-stage C–H fluorination is an appealing reaction for medicinal chemistry. However, the application of this strategy to process research appears less attractive due to the formation and necessary purification of mixtures of organofluorines. Here we demonstrate that γ-fluoroleucine methyl ester, an intermediate critical to the large-scale synthesis of odanacatib, can be accessed directly from leucine methyl ester using a combination of the decatungstate photocatalyst and N-fluorobenzenesulfonimide in flow. This efficient C–H fluorination reaction compares favorably with several generations of classical γ-fluoroleucine process syntheses. Late-stage C-H fluorination is an appealing reaction for medicinal chemistry. However, the application of this strategy to process research appears less attractive due to the formation and necessary purification of mixtures of organofluorines. Here we demonstrate that γ-fluoroleucine methyl ester, an intermediate critical to the large-scale synthesis of odanacatib, can be accessed directly from leucine methyl ester using a combination of the decatungstate photocatalyst and N-fluorobenzenesulfonimide in flow. This efficient C-H fluorination reaction compares favorably with several generations of classical γ-fluoroleucine process syntheses. |
| Author | Campeau, Louis-Charles DiRocco, Daniel A Halperin, Shira D Holmes, Michael Kwon, Daniel Britton, Robert Regalado, Erik L |
| AuthorAffiliation | Department of Chemistry Merck Research Laboratories Department of Process Chemistry Simon Fraser University |
| AuthorAffiliation_xml | – name: Department of Process Chemistry – name: Merck Research Laboratories – name: Department of Chemistry – name: Simon Fraser University |
| Author_xml | – sequence: 1 givenname: Shira D surname: Halperin fullname: Halperin, Shira D – sequence: 2 givenname: Daniel surname: Kwon fullname: Kwon, Daniel – sequence: 3 givenname: Michael surname: Holmes fullname: Holmes, Michael – sequence: 4 givenname: Erik L surname: Regalado fullname: Regalado, Erik L – sequence: 5 givenname: Louis-Charles surname: Campeau fullname: Campeau, Louis-Charles – sequence: 6 givenname: Daniel A surname: DiRocco fullname: DiRocco, Daniel A email: daniel.dirocco@merck.com – sequence: 7 givenname: Robert surname: Britton fullname: Britton, Robert email: rbritton@sfu.ca |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/26484983$$D View this record in MEDLINE/PubMed |
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| SubjectTerms | Biphenyl Compounds - chemical synthesis Biphenyl Compounds - chemistry Cathepsin K - antagonists & inhibitors Esters Halogenation Leucine - analogs & derivatives Leucine - chemistry Molecular Structure Sulfonamides - chemistry |
| Title | Development of a Direct Photocatalytic C–H Fluorination for the Preparative Synthesis of Odanacatib |
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