反应详情

To a solution of N-methyl morpholine-N-oxide (50% wt solution in water, 0.103 g, 0.44 mmol) in THF and water (1 mL/0.3 mL) was added 0.096 mL (0.38 mmol) of osmium tetroxide (2.5 wt % in t-butanol). To that solution was quickly added 0.21 g (0.38 mmol) of methyl N-[(4′-{[(3-methyl-4-vinyl-1-benzofuran-2-yl)carbonyl]amino}-1,1′-biphenyl-4-yl)sulfonyl]-L-valinate (Example 96, Step 2). The reaction was stirred at room temperature for 2 hours and then quenched with excess sodium hydrosulfite in water. The reaction mixture was extracted with ethyl acetate and water. The organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated to provide 0.19 g of methyl N-{[4′-({[4-(1,2-dihydroxyethyl)-3-methyl-1-benzofuran-2-yl]carbonyl}amino)-1,1′-biphenyl-4-yl]sulfonyl}-L-valinate. Yield 85.2%. m.p. 90-95° C. MS: 581.2 (M+H)+.

1. customquenched with excess sodium hydrosulfite in water
2. extractionThe reaction mixture was extracted with ethyl acetate and water
3. washThe organic layer was washed with water and brine
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated