反应详情

Combine (S)-N-methyl-N-(2-(4-fluorophenyl)pent-4-enyl)-2-methoxy-5-(1H-tetrazol-1-yl)benzamide (4.46 g, 11.3 mmol), acetone/t-butanol/water (2/1/1, 64 mL), and a solution of N-methylmorpholine N-oxide (3.0 mL, 50% in water, 14.5 mmol). Add a solution of osmium tetraoxide (3.0 mL, 4% in water, 0.5 mmol). After 3 hours, evaporate in vacuo to remove most of the acetone and partition the evaporated reaction mixture between dichloromethane and an aqueous 10% solution of sodium thiosulfate. Separate the layer, dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Combine the residue, tetrahydrofuran (80 mL), and water (20 mL). Add sodium meta-periodate (3.63 g). After 1.5 hours, filter the reaction mixture, rinse the solids with dichloromethane, and evaporate the filtrate to obtain a residue. Chromatograph the residue on silica gel eluting with ethyl acetate to give the title compound: Rf=0.22 (silica gel, ethyl acetate).

1. customevaporate in vacuo
2. customto remove most of the acetone
3. custompartition
4. customthe evaporated reaction mixture between dichloromethane
5. customSeparate the layer
6. dry with materialdry the organic layer over MgSO4
7. filtrationfilter
8. customevaporate in vacuo
9. customto give a residue
10. waitAfter 1.5 hours
11. filtrationfilter the reaction mixture
12. washrinse the solids with dichloromethane
13. customevaporate the filtrate
14. customto obtain a residue