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

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[[4-(2,2-difluoroethoxy)phenyl]methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol 12e (4 g, 8.43 mmol) was dissolved in 40 mL dichloromethane, followed by addition of DMAP (103 mg, 0.84 mmol), TBSCl (1.4 g, 9.27 mmol) and imidazole (1.72 g, 25.3 mmol) in turn. The reaction mixture was stirred for 16 hours. 40 mL saturated sodium bicarbonate were added before the reaction mixture was stirred and partitioned. Thereafter, the organic extract was washed with 0.1 N hydrochloric acid (20 mL) and saturated sodium chloride solution (40 mL), dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (2S,3R,4S,5S,6R)-6-[(tert-butyl(dimethyl)silyl)oxymethyl]-2-[4-chloro-3-[[4-(2,2-difluoroethoxy)phenyl]methyl]phenyl]-2-methoxy-tetrahydropyran-3,4,5-triol 12f (4.96 g, pale yellow solid), yield: 100%.

1. stirringwas stirred
2. custompartitioned
3. extractionThereafter, the organic extract
4. washwas washed with 0.1 N hydrochloric acid (20 mL) and saturated sodium chloride solution (40 mL)
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationThe filtrate was concentrated under reduced pressure

ORD 기록

ord-1f1cbdbf180f4233bb78c7550884c50b

출처 데이터셋

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08609622B2