Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Bromide | HCID 253881 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Tempo | HCID 2724126 | — |
| Reactant | Sodium Hypochlorite | HCID 23665760 | — |
| Reactant | (1s,3ar,6as)-2-[(2s)-2-({(2s)-2-Cyclohexyl-2-[(Pyrazin-2-Ylcarbonyl)amino]acetyl}amino)-3,3-Dimethylbutanoyl]-N-[(2r,3s)-1-(Cyclopropylamino)-2-Hydroxy-1-Oxohexan-3-Yl]octahydrocyclopenta[c]pyrrole-1-Carboxamide | HCID 59235547 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Telaprevir | HCID 3010818 | — |
Reaction Steps
Compound 45 (2.0 g, 2.9 mmol) was dissolved in dichloromethane (14 mL), and to this solution was added a solution of sodium bromide (144 mg) in water (1.0 mL) followed by a solution of sodium bicarbonate (300 mg) in water (4.0 mL). The mixture was cooled to 0° C., whereupon TEMPO (53 mg, 0.34 mmol) was added. Commercial bleach solution containing sodium hypochlorite (3.3 mL) further diluted with water (9.6 mL) was added drop-wise over the course of 10 minutes. The mixture was stirred 1.5 hours at 5° C. after which the organic layer was separated and washed with 10% aqueous sodium sulfite (8 mL) then brine. The resulting solution was dried over magnesium sulfate, filtered, and then concentrated to dryness. After crystallization from dichloromethane/ethyl acetate, compound 4 showed spectroscopic properties identical to those reported in Example 14.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08871904B2 |
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| Source dataset | uspto-grants-2014_10 |
|---|
| ORD ID | ord-d516ced2abbe42b99308bde6b7054a3c |
|---|
| Source note | uspto-grants-2014_10 |
|---|
