Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | 2,5-Dimethoxytetrahydrofuran | HCID 79098 | — |
| Reactant | HCID 57951106 | HCID 57951106 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 57951148 | HCID 57951148 | — |
Reaction Steps
Charge THF (20 mL, 5 vols) to a flask containing (±)-5-(3-methyl-phenyl)-1-(4-trifluoromethoxy-phenyl)-3-(4-trifluoromethoxy-phenylamino)-1,5-dihydro-pyrrol-2-one (4.18 g, 8.22 mmol). Add acetic acid (1.88 mL, 32.89 mmol,) to the above clear solution to afford a yellow solution. Add 2,5-dimethoxytetrahydrofuran (1.28 mL, 9.87 mmol,), then add water (0.2 mL, 9.87 mmol). Add TFA (1.25 mL, 16.44 mmol,) to the reaction mixture and observe a slight exotherm (23 to 30° C.). Heat the reaction mixture to 40° C. for 22 hours. Pour the brown solution into water (50 mL) and extract with ethyl acetate (50 mL×2). Wash the organic phase with saturated sodium bicarbonate solution (20 mL×2), brine (50 mL), dry over magnesium sulfate and evaporate to afford the titled compound. MS (m/z): 350.1 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08168659B2 |
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| Source dataset | uspto-grants-2012_05 |
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| ORD ID | ord-a50f7429b35b4707a15093b3a3813ced |
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| Source note | uspto-grants-2012_05 |
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