反应详情

A solution of tert-butyl 2-{4-[2-ethyl-4-(4-fluorophenyl)-1H-imidazol-1-yl]phenyl}ethylcarbamate (1.1 g, 2.6 mmol) in 10% HCl-MeOH (20 mL) was heated at 50° C. for 2 h. After cooling, the volatile components were removed by evaporation and the resulting amorphous was dried under reduced pressure. Then, the amorphous was suspended in dichloromethane at 0° C. To the cooled mixture was added triethylamine (1.4 mL, 10 mmol) and phenyl chloroformate (380 μL, 3.0 mmol). After 1 h, the reaction mixture was partitioned between ethyl acetate (30 mL) and water (10 mL). The aqueous phase was extracted with ethyl acetate (3×30 mL) and the combined organic phase was dried (MgSO4) and concentrated under reduced pressure. Purification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 3:1 to 2:1) afforded 924 mg (85%) of the title compound as colorless amorphous. MS (ESI) m/z 430 [M+H]+.

1. temperatureAfter cooling
2. customthe volatile components were removed by evaporation
3. customthe resulting amorphous was dried under reduced pressure
4. customwas suspended in dichloromethane at 0° C
5. customthe reaction mixture was partitioned between ethyl acetate (30 mL) and water (10 mL)
6. extractionThe aqueous phase was extracted with ethyl acetate (3×30 mL)
7. dry with materialthe combined organic phase was dried (MgSO4)
8. concentrationconcentrated under reduced pressure
9. customPurification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 3:1 to 2:1)