Acetic Acid → HCID 57951148, compound
Reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=3)[C:11](=[O:24])[C:10](NC3C=CC(OC(F)(F)F)=CC=3)=[CH:9]2)[CH:5]=[CH:6][CH:7]=1.C(O)(=[O:39])C.COC1CCC(OC)O1.C(O)(C(F)(F)F)=O>O.C1COCC1>[OH:39][C:10]1[C:11](=[O:24])[N:12]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]([F:22])([F:23])[F:21])=[CH:15][CH:14]=2)[CH:8]([C:4]2[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][CH:5]=2)[CH:9]=1Participants
Conditions
- Temperature
- 40 °C
Procedure
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).
Workup
- customa slight exotherm (23 to 30° C.)
- extractionextract with ethyl acetate (50 mL×2)
- washWash the organic phase with saturated sodium bicarbonate solution (20 mL×2), brine (50 mL)
- dry with materialdry over magnesium sulfate
- customevaporate
Sources & evidence
- ORD record
- ord-a50f7429b35b4707a15093b3a3813ced
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08168659B2
Reaction notes
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