反应详情

6-(4-Bromo-2-methyl-phenylamino)-7-fluoro-3-pent-4-enyl-3H-benzoimidazole-5-carboxylic acid cyclopropylmethoxy-amide 11f (0.307 g, 0.612 mmol) is dissolved in 4:1 THF/water (8 mL) and 1.134 mL (0.061 mmol) of an 0.054 M OsO4 solution in t-BuOH iias added followed by NMO (0.093 g, 0.796 mmol). After 5 hours, the reaction mixture is quenched by the addition of 10% NaHS2O3 solution. After 10 minutes, the reaction mixture is filtered through Celite rinsing with ethyl acetate and methylene chloride. The filtrate is diluted with ethyl acetate and washed with 0.01 N HCl, and brine. The organic layer is dried (Na2SO4) and concentrated under reduced pressure. The crude product is purified by FCC eluted with 9:1 ethyl acetate/MeOH to give 0.244 g (74%) pure desired product.

1. additionadded
2. customthe reaction mixture is quenched by the addition of 10% NaHS2O3 solution
3. waitAfter 10 minutes
4. filtrationthe reaction mixture is filtered through Celite
5. washrinsing with ethyl acetate and methylene chloride
6. additionThe filtrate is diluted with ethyl acetate
7. washwashed with 0.01 N HCl, and brine
8. dry with materialThe organic layer is dried (Na2SO4)
9. concentrationconcentrated under reduced pressure
10. customThe crude product is purified by FCC
11. washeluted with 9:1 ethyl acetate/MeOH