m-Chloroperbenzoic acid → HCID 118666119, compound
Reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][S:13][C:14]1[C:22]2[C:17](=[CH:18][C:19]([C:23]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[O:24])=[CH:20][CH:21]=2)[N:16]([C:31]2[N:36]=[CH:35][C:34]([C:37]3[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=3)=[CH:33][N:32]=2)[CH:15]=1>ClCCl>[CH3:12][S:13]([C:14]1[C:22]2[C:17](=[CH:18][C:19]([C:23]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[O:24])=[CH:20][CH:21]=2)[N:16]([C:31]2[N:32]=[CH:33][C:34]([C:37]3[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=3)=[CH:35][N:36]=2)[CH:15]=1)=[O:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
m-Chloroperoxybenzoic acid (48 mg, 0.21 mmol) was added at 0° C. to a solution of 49a) (0.18 g, 0.25 mmol) in dichloromethane (20 mL) and the resulting mixture was stirred at room temperature for 4 h. The reaction was quenched with saturated sodium sulfite solution (20 mL) and stirred for further 5 min. The organic layer was separated, washed with saturated sodium hydrogen carbonate solution (2×20 mL) and brine (1×20 mL), dried over sodium sulphate and concentrated. The residue was purified by flash column chromatography [methanol/dichloromethane=1:25]. White solid. Yield: 0.06 g (53% of theory)
Workup
- customThe reaction was quenched with saturated sodium sulfite solution (20 mL)
- stirringstirred for further 5 min
- customThe organic layer was separated
- washwashed with saturated sodium hydrogen carbonate solution (2×20 mL) and brine (1×20 mL)
- dry with materialdried over sodium sulphate
- concentrationconcentrated
- customThe residue was purified by flash column chromatography [methanol/dichloromethane=1:25]
Sources & evidence
- ORD record
- ord-1ac9d564dbb54daca32566b8ce3ddea3
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315490B2
Reaction notes
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