Imidazole → (2S,3R,4S,5S,6R)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-[4-chloro-3-[(2,3-difluoro-4-methoxy-phenyl)methyl]phenyl]-2-methoxy-tetrahydropyran-3,4,5-triol

To a solution of (2S,3R,4S,5S,6R)-2-[4-chloro-3-[(2,3-difluoro-4-methoxy-phenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol 21h (1.12 g, 2.38 mmol) in dichloromethane (20 mL) were added tert-butyldimethylsilyl chloride (0.54 g, 3.58 mmol) and imidazole (0.49 g, 7.16 mmol) in turn at room temperature. The mixture was stirred at room temperature for 3 hours. The mixture was partitioned between dichloromethane (40 mL) and water (40 mL). The organic layer was washed with saturated aqueous sodium chloride (30 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound 21i as yellow oil (1.37 g, 100%).

1. customThe mixture was partitioned between dichloromethane (40 mL) and water (40 mL)
2. washThe organic layer was washed with saturated aqueous sodium chloride (30 mL)
3. dry with materialdried over anhydrous sodium sulfate
4. filtrationfiltered
5. concentrationThe filtrate was concentrated in vacuo

ORD-Eintrag

ord-d433709c48f44e6bb1ba35282583650b

Quelldatensatz

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09394329B2