反应详情

Combine (S)-N-methyl-N-(2-(3,4-dichlorophenyl)pent-4-enyl)-2-methoxy-5-(1H-tetrazol-1-yl)benzamide (5.12 g, 11.5 mmol), acetone/t-butanol/water (2/1/1, 120 mL), and a solution of N-methylmorpholine N-oxide (3.3 g 50% in water). Add a solution of osmium tetraoxide (4.4 g, 4% in water, 13.8 mmol). After 2 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 layers, extract the organic layer with brine, dry over MgSO4, filter, and evaporate in vacuo to give a residue. Combine the residue and tetrahydrofuran/water (4/1 150 mL). Add sodium meta-periodate (2.95 g, 13.8 mmol). After 1.5 hours, filter the reaction mixture, rinse the solids with tetrahydrofuran, and evaporate the filtrate to remove most of the tetrahydrofuran. Dilute the evaporated reaction mixture with dichloromethane. Extract with water, dry over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with 1% methanol/dichloromethane, 2% methanol/dichloromethane, and 3% methanol/dichloromethane to give the title compound: Rf=0.20 (silica gel, 6% methanol/dichloromethane).

1. customevaporate in vacuo
2. customto remove most of the acetone
3. custompartition
4. customthe evaporated reaction mixture between dichloromethane
5. customSeparate the layers
6. extractionextract the organic layer with brine
7. dry with materialdry over MgSO4
8. filtrationfilter
9. customevaporate in vacuo
10. customto give a residue
11. waitAfter 1.5 hours
12. filtrationfilter the reaction mixture
13. washrinse the solids with tetrahydrofuran
14. customevaporate the filtrate
15. customto remove most of the tetrahydrofuran
16. additionDilute
17. customthe evaporated reaction mixture with dichloromethane
18. extractionExtract with water
19. dry with materialdry over MgSO4
20. filtrationfilter
21. customevaporate in vacuo
22. customto give a residue