Methanol → 2-Fluoro-3-(4-trifluoromethyl-benzenesulfonylamino)-benzoic acid methyl ester
Reaction equation
[F:1][C:2]1[C:10]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:30]O>>[CH3:30][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:22])[F:23])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[C:2]=1[F:1]Participants
Procedure
To 2-fluoro-3-(4-trifluoromethyl-benzenesulfonylamino)-benzoic acid (23, 4.0 g, 11 mmol) in 40 mL of methanol, sulfuric acid (8.8 mL, 0.16 mol) was added and the reaction mixture was refluxed overnight. The resulting reaction mixture was concentrated, and the residue was poured into 5% aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified with silica gel column chromatography eluting with 20% ethyl acetate in hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (24, 3.35 g, 81%). MS (ESI) [M−H+]−=376.4.
Workup
- temperaturethe reaction mixture was refluxed overnight
- customThe resulting reaction mixture
- concentrationwas concentrated
- additionthe residue was poured into 5% aqueous sodium bicarbonate solution
- extractionextracted with ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationthe filtrate concentrated under vacuum
- customThe resulting material was purified with silica gel column chromatography
- washeluting with 20% ethyl acetate in hexane
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-34ac73adb15a4b24bb037e959a4e7dc3
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08110576B2
Reaction notes
Loading…