Sodium hydride → 3-Isopropyl-4-(3'-methanesulfonyl-biphenyl-3-yl)-1-(propane-2-sulfonyl)-imidazolidin-2-one
Reaction equation
[CH:1]([N:4]1[CH:8]([C:9]2[CH:10]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:16]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:7][NH:6][C:5]1=[O:25])([CH3:3])[CH3:2].[H-].[Na+].[CH:28]([S:31](Cl)(=[O:33])=[O:32])([CH3:30])[CH3:29]>CN(C)C(=O)C>[CH:1]([N:4]1[CH:8]([C:9]2[CH:10]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([S:21]([CH3:24])(=[O:22])=[O:23])[CH:16]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:7][N:6]([S:31]([CH:28]([CH3:30])[CH3:29])(=[O:33])=[O:32])[C:5]1=[O:25])([CH3:3])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 1-isopropyl-5-(3′-methanesulfonyl-biphenyl-3-yl)-imidazolidin-2-one (40 mg) in N,N-dimethylacetamide (1 mL) under argon at 0° C. was added sodium hydride dispersion (55% in mineral oil, 6 mg). The mixture was stirred at 0° C. for 1.5 h. Isopropylsulfonylchloride (19 mg) was added. The mixture was stirred for 30 min at 0° C. and overnight at room temperature. Ice cold water was added and the mixture was extracted with ethyl acetate. The org. phase was washed with water and concentrated. The product was purified using column chromatography (SiO2, cyclohexane/ethyl acetate 1:0=>0:1) to give 3-isopropyl-4-(3′-methanesulfonyl-biphenyl-3-yl)-1-(propane-2-sulfonyl)-imidazolidin-2-one (28 mg) as a colorless foam. MS: 465.3 ([M+H]+)
Workup
- stirringThe mixture was stirred for 30 min at 0° C. and overnight at room temperature
- additionIce cold water was added
- extractionthe mixture was extracted with ethyl acetate
- washphase was washed with water
- concentrationconcentrated
- customThe product was purified
Sources & evidence
- ORD record
- ord-745ad221c334444981593138549636f3
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063088B2
Reaction notes
Loading…