HCID 10542009, compound → HCID 59556931, compound

Ethyl 4-[(tert-butoxycarbonyl)amino]-2,4,5-trideoxy-2,2-difluoro-L-threo-pentonate (5.45 g) was dissolved in a 4 mol/L solution (100 mL) of hydrogen chloride/ethyl acetate, and the mixture was stirred at room temperature for 1.5 hr. The reaction solution was concentrated under reduced pressure, THF (200 mL) and diisopropylethylamine (9.9 mL) were added thereto, and the mixture was heated under reflux for 3 hr. The reaction solution was concentrated under reduced pressure and water (50 mL) was added to the residue. The mixture was extracted with ethyl acetate (100 mL×5) and ethyl acetate/THF=2/1 (100 mL×3). The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was washed with diisopropyl ether to give the title compound as a white powder (yield: 1.55 g, 46%).

1. concentrationThe reaction solution was concentrated under reduced pressure, THF (200 mL) and diisopropylethylamine (9.9 mL)
2. additionwere added
3. temperaturethe mixture was heated
4. temperatureunder reflux for 3 hr
5. concentrationThe reaction solution was concentrated under reduced pressure and water (50 mL)
6. additionwas added to the residue
7. extractionThe mixture was extracted with ethyl acetate (100 mL×5) and ethyl acetate/THF=2/1 (100 mL×3)
8. dry with materialThe extract was dried over anhydrous magnesium sulfate
9. concentrationconcentrated under reduced pressure
10. washThe residue was washed with diisopropyl ether

ORD record

ord-946b4cfe03f2486c8a20cac297b1fc3e

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08420694B2