Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triacetoxyperiodinane | HCID 159087 | — |
| Reactant | Tempo | HCID 2724126 | — |
| Reactant | Telaprevir, (alpha-ketoamide bond reduced)- | HCID 23634854 | — |
| Reactant | Sodium Hypochlorite | HCID 23665760 | — |
| Reactant | Sodium Bisulfite | HCID 23665763 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Telaprevir | HCID 3010818 | — |
Reaction Steps
The title compound is prepared by oxidation of the product of Step h with a suitable oxidizing reagent such as Dess-Martin periodinane or TEMPO and sodium hypochlorite. Specifically, in a flask containing 1.31 g of (1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((3S)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide in 40 mL of dichloromethane is added at room temperature 1.06 g of Dess-Martin periodinane. After 2 hours of stirring, 50 mL of sodium bisulfite (1N) is added, and the mixture is stirred for 30 minutes. The 2 phases are separated, the organic is washed with water twice, brine and dried over Na2SO4. The crude product was purified by chromatography on silica (ethyl acetate 20-100% in Hexanes) to give the title compound. The diastereoisome ratio is determined by chiral HPLC normal phase.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08383858B2 |
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| Source dataset | uspto-grants-2013_02 |
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| ORD ID | ord-db32157f4c124b77bce2000049c4d30d |
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| Source note | uspto-grants-2013_02 |
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