Water → HCID 66975055, compound

Reaction equation

[O:1]=[C:2]1[CH2:8][O:7][CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.[Cl:16][C:17]1[CH:18]=[C:19]([Mg]Br)[CH:20]=[CH:21][C:22]=1[Cl:23].C1COCC1.O>C1COCC1>[Cl:16][C:17]1[CH:18]=[C:19]([C:2]2([OH:1])[CH2:8][O:7][CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]2)[CH:20]=[CH:21][C:22]=1[Cl:23]

Participants

Procedure

To a solution of tert-butyl 6-oxo-1,4-oxazepane-4-carboxylate (418 mg) prepared by the method described in WO2004/074291 in THF (12 mL) was added 0.5 M 3,4-dichlorophenylmagnesium bromide-THF (4.7 mL) under ice-cooling. The reaction mixture was stirred at room temperature for 1.5 hr, and poured into water, and the mixture was extracted with ethyl acetate. The extract was washed successively with dil. hydrochloric acid, saturated aqueous sodium hydrogen carbonate, water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (455 mg).