Methanol → 2-Fluoro-3-(propane-1-sulfonylamino)-benzoic acid methyl ester
Reaction equation
[F:1][C:2]1[C:10]([NH:11][S:12]([CH2:15][CH2:16][CH3:17])(=[O:14])=[O:13])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:18]N(C)C=O.C(Cl)(=O)C(Cl)=O.CO>ClCCl>[CH3:18][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([NH:11][S:12]([CH2:15][CH2:16][CH3:17])(=[O:14])=[O:13])[C:2]=1[F:1]Participants
Procedure
To a 2-fluoro-3-(propane-1-sulfonylamino)-benzoic acid (15, 5.05 g, 19.3 mmol) in 100 mL of dichloromethane, N,N-dimethylformamide (0.075 mL, 0.97 mmol) was added under an atmosphere of nitrogen. The reaction was cooled with ice water bath, followed by slow addition of oxalyl chloride (10.8 mL, 2.00 M in dichloromethane, 21.6 mmol). The reaction mixture was stirred at room temperature for 3.0 hours, then cooled with ice water bath, followed by slowly adding 36.0 mL of methanol. The reaction was stirred at room temperature overnight, then concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with 30% ethyl acetate in hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound as a crude white solid (16, 4.0 g).
Workup
- temperatureThe reaction was cooled with ice water bath
- temperaturecooled with ice water bath
- stirringThe reaction was stirred at room temperature overnight
- concentrationconcentrated under vacuum
- customThe resulting material was purified by silica gel column chromatography
- washeluting with 30% ethyl acetate in hexane
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-6baa9b1b74774018865178bdec72054f
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08153641B2
Reaction notes
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