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
4
Procedure
To 2-fluoro-3-(4-trifluoromethyl-benzenesulfonylamino)-benzoic acid (31, 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 under vacuum, and the residue was combined with 5% aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under vacuum and purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (32, 3.35 g, 81%). MS(ESI) [M−H+]−=376.4.
Workup
- temperaturethe reaction mixture was refluxed overnight
- customThe resulting reaction mixture
- concentrationwas concentrated under vacuum
- extractionextracted with ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationThe filtrate was concentrated under vacuum
- custompurified by silica gel column chromatography
- washeluting with 20% ethyl acetate in hexane
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-e92aa6bcbca2434ca23606baca911647
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08153641B2
Reaction notes
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