m-Chloroperbenzoic acid → HCID 54204990, compound
Reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([N:19]1[C:31]2[C:30]([S:32]([CH3:34])=[O:33])=[C:29]([CH2:35][C:36]([O:38][CH:39]([CH3:41])[CH3:40])=[O:37])[CH:28]=[C:27]([CH3:42])[C:26]=2[C:25]2[C:20]1=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH2:12]([N:19]1[C:31]2[C:30]([S:32]([CH3:34])(=[O:9])=[O:33])=[C:29]([CH2:35][C:36]([O:38][CH:39]([CH3:40])[CH3:41])=[O:37])[CH:28]=[C:27]([CH3:42])[C:26]=2[C:25]2[C:20]1=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
44 mg (0.25 mmol) of m-chloroperbenzoic acid was added to 6 ml of a solution of 100 mg (0.23 mmol) of isopropyl (9-benzyl-1-methylsulfinyl-4-methylcarbazol-2-yl)acetate, as obtained in Example 215 below, in methylene chloride at room temperature, and the mixture was stirred for 30 minutes. After this time, a saturated aqueous solution of sodium hydrogencarbonate was added to the mixture, the aqueous layer was extracted with methylene chloride, the extract was dried over anhydrous magnesium sulfate and then the solvent was removed by evaporation under reduced pressure. The residue was subjected to column chromatography (eluent: a 50% v/v solution of ethyl acetate in hexane) to yield 90 mg (87%) of the title compound as an amorphous solid.
Workup
- extractionthe aqueous layer was extracted with methylene chloride
- dry with materialthe extract was dried over anhydrous magnesium sulfate
- customthe solvent was removed by evaporation under reduced pressure
Sources & evidence
- ORD record
- ord-83aec3bbd35c4b4e968b7a6010064d4d
- Source dataset
- uspto-grants-1999_03
- Patent number
- US05877199
Reaction notes
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