反应详情

To a solution of (R)-5-[4-(2-tert-butoxy-ethoxy)-phenyl]-3-[(S)-1-(5-iodo-1H-benzoimidazol-2-yl)-2-phenyl-ethyl]-imidazolidine-2,4-dione (140 mg, 0.22 mmol) in 1:1 v/v dichloromethane/acetonitrile (2 mL) at 0° C. under an atmosphere of nitrogen was added sodium iodide (62 mg, 0.42 mmol) followed by chlorotrimethylsilane (78 μL, 0.61 mmol), the resulting solution was allowed to stir for 30 minutes. Additional sodium iodide (62 mg, 0.42 mmol) followed by chlorotrimethylsilane (78 μL, 0.61 mmol) was added and stirring continued for a further 45 minutes. The reaction was poured into ethyl acetate (30 mL) and washed with 10% aqueous sodium thiosulfate solution. The organic extract was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by chromatography over silica gel gradient eluted with 60 to 80% v/v ethyl acetate/hexanes to give (R)-5-[4-(2-hydroxy-ethoxy)-phenyl]-3-[(S)-1-(5-iodo-1H-benzoimidazol-2-yl)-2-phenyl-ethyl]-imidazolidine-2,4-dione (83 mg, 65%).

1. additionwas added
2. stirringstirring
3. waitcontinued for a further 45 minutes
4. washwashed with 10% aqueous sodium thiosulfate solution
5. extractionThe organic extract
6. washwas washed with brine
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe crude product was purified by chromatography over silica gel gradient
11. washeluted with 60 to 80% v/v ethyl acetate/hexanes