m-Chloroperbenzoic acid → HCID 57736442, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]([S:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)[C:10]1[C:11]([CH3:22])=[CH:12][C:13]([C:16]([NH:18][CH2:19][CH2:20][OH:21])=[O:17])=[N:14][CH:15]=1.ClC1C=CC=C(C(OO)=[O:39])C=1>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]([S:23]([C:24]1[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=1)=[O:39])[C:10]1[C:11]([CH3:22])=[CH:12][C:13]([C:16]([NH:18][CH2:19][CH2:20][OH:21])=[O:17])=[N:14][CH:15]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 5-[(2,5-difluorophenyl)[(4-fluorophenyl)thio]methyl]-N-(2-hydroxyethyl)-4-methylpyridine-2-carboxamide (478 mg, 1.11 mmol) in methylene chloride (15 ml), 3-chloroperbenzoic acid (293 mg, 1.11 mmol) was added at 0° C. After stirring for 3 hours at the same temperature, the reaction mixture was washed with 1 N aqueous sodium hydroxide, the organic layer was dried over anhydrous sodium sulfate and filtered, and then the filtrate was concentrated under reduced pressure. The resulting residue was subjected to flash silica gel chromatography, and the fraction obtained from an elution with hexane:ethyl acetate=1:2 was concentrated under reduced pressure. The resulting residue was washed with hexane, and then the residue was dried under reduced pressure, to obtain the title compound (238 mg, 0.53 mmol, 48%) as a colorless foamy substance.