Dibromomethane → Ethyl 6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]-1-oxaspiro[2.5]oct-4-ene-5-carboxylate
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH:13]1[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][C:16](=[O:24])[CH2:15][CH2:14]1)(=[O:12])=[O:11].Br[CH2:26]Br.C([Li])CCC.CCCCCC.[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH:13]1[CH2:14][CH2:15][C:16]2([O:24][CH2:26]2)[CH:17]=[C:18]1[C:19]([O:21][CH2:22][CH3:23])=[O:20])(=[O:12])=[O:11]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
50 mg (0.133 mmol) of ethyl 6-[1-(2-chloro-4-fluorophenyl)sulfamoyl]-3-oxo-1-cyclohexene-1-carboxylate obtained in Example 7 and 0.01 ml (0.146 mmol) of dibromomethane were dissolved in 1 ml of tetrahydrofuran, and 0.18 ml (0.279 mmol) of n-butyllithium/hexane solution (1.58 M) was added dropwise thereto at −78° C., followed by stirring at room temperature for 4 hours. After the reaction solution was cooled with ice, a saturated aqueous ammonium chloride solution was added and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was subjected to silica gel thin layer chromatography (solvent; hexane:ethyl acetate=2:1) to give 7 mg of the title compound as a yellow oil (yield: 14%).
Workup
- customat −78° C.
- temperatureAfter the reaction solution was cooled with ice
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- concentrationfollowed by concentration under reduced pressure
Sources & evidence
- ORD record
- ord-96ba0f63e6d6403a84a99df1466d93a1
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07935835B2
Reaction notes
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