Reaction equation
[CH3:1][C:2]([S@@:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[I-].C([Zn+])C(C)(C)C.[Br:15][C:16]1[CH:17]=[CH:18][C:19]([O:29][CH2:30][O:31][CH3:32])=[C:20]([C:22](=O)[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:21]=1>>[Br:15][C:16]1[CH:17]=[CH:18][C:19]([O:29][CH2:30][O:31][CH3:32])=[C:20]([C:22](=[N:7][S@:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:21]=1Participants
Procedure
A flask was charged with (S)-2-methylpropane-2-sulfinamide (0.764 g, 6.31 mmol) and neopentylzinc (II) iodide (0.5 M in THF, 10.0 mL, 5.00 mmol) was added under nitrogen atmosphere. The mixture was stirred at RT for 15 minutes and ethyl 2-(5-bromo-2-(methoxymethoxy)phenyl)-2-oxoacetate (1.00 g, 3.15 mmol) was added in one portion. The reaction mixture was quenched with saturated aqueous ammonium chloride after 8 h. The reaction was partitioned between EtOAc and water. The organic phase was separated, washed with NH4Cl, water and brine. The organic phase was dried over MgSO4 and the solvent was removed under reduced pressure. The crude material was purified by silica gel chromatography (10-30% EtOAc/hexane) to provide 0.675 g (S)-ethyl 2-(5-bromo-2-(methoxymethoxy)phenyl)-2-(tert-butylsulfinylimino)acetate.
Workup
- additionwas added under nitrogen atmosphere
- customThe reaction mixture was quenched with saturated aqueous ammonium chloride after 8 h
- customThe reaction was partitioned between EtOAc and water
- customThe organic phase was separated
- washwashed with NH4Cl, water and brine
- dry with materialThe organic phase was dried over MgSO4
- customthe solvent was removed under reduced pressure
- customThe crude material was purified by silica gel chromatography (10-30% EtOAc/hexane)
Sources & evidence
- ORD record
- ord-cbf88d31c70f44be998e78d6df4a066d
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08497264B2
Linked notes
Loading…