Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium Thiosulfate | HCID 24477 | — |
| Reactant | m-Chloroperbenzoic acid | HCID 70297 | — |
| Reactant | HCID 67395914 | HCID 67395914 | — |
| Product | HCID 67397600 | HCID 67397600 | 92% |
Reaction Steps
To a solution of tert-butyl {[4-fluoro-5-(2-fluoropyridin-3-yl)-1-({3-[(methylthio)methyl]phenyl}sulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (235 mg) in ethyl acetate (3 mL) was added dropwise a solution of 3-chloroperbenzoic acid (620 mg) in ethyl acetate (2 mL) under ice-cooling, and the mixture was stirred for 2 hr. Saturated aqueous sodium thiosulfate solution was added, and the mixture was extracted with ethyl acetate. The separated organic layer was washed with saturated aqueous sodium hydrogen carbonate solution. The separated aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→2:3) to give the title compound as a pale-yellow oil (yield 231 mg, 92%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08933105B2 |
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| Source dataset | uspto-grants-2015_01 |
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| ORD ID | ord-1b19977cd01647cdbfe3e8e650f125f3 |
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| Source note | uspto-grants-2015_01 |
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