反应详情

Combine (S)-N-methyl-N-(2-phenylpent-4-enyl)-2-methoxy-5-(1H-tetrazol-1-yl)benzamide (3.13 g, 8.3 mmol), acetone/t-butanol/water (2/1/1, 90 mL), and a solution of N-methylmorpholine N-oxide (2.06 mL, 50% in water, 9.95 mmol). Add a solution of osmium tetraoxide (2.56 mL, 4% in water, 0.5 mmol). After 18 hours, evaporate in vacuo to remove most of the acetone and extract the evaporated reaction mixture with dichloromethane. Extract the organic layer with an aqueous 10% solution of sodium thiosulfate. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue: Rf=0.22 (silica gel, 7% methanol/dichloromethane/0.1% concentrated ammonium hydroxide). Combine the residue (3.6 g, 8.3 mmol) and tetrahydrofuran/water (90 mL, 4/1). Add sodium meta-periodate (2.13 g, 9.95 mmol). After 1 hour, filter the reaction mixture, rinse the solids with tetrahydrofuran, and evaporate the filtrate to obtain a residue. Dilute the residue with ethyl acetate (150 mL), extract with brine, dry over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 5% methanol/dichloromethane/0.1% concentrated ammonium hydroxide to give the title compound: Rf=0.33 (silica gel, 7% methanol/dichloromethane/0.1% concentrated ammonium hydroxide). [α]2D0=13.70° (c=0.59, chloroform)

1. customevaporate in vacuo
2. customto remove most of the acetone
3. extractionextract
4. customthe evaporated reaction mixture with dichloromethane
5. extractionExtract the organic layer with an aqueous 10% solution of sodium thiosulfate
6. dry with materialDry the organic layer over MgSO4
7. filtrationfilter
8. customevaporate in vacuo
9. customto give a residue
10. waitAfter 1 hour
11. filtrationfilter the reaction mixture
12. washrinse the solids with tetrahydrofuran
13. customevaporate the filtrate
14. customto obtain a residue
15. extractionextract with brine
16. dry with materialdry over MgSO4
17. filtrationfilter
18. customevaporate in vacuo
19. customto give a residue