Hydrochloric Acid → HCID 178475073, compound

Temperature

-78 °C

n-Butyllithium (1.6M hexane solution, 11.4 mL) was added dropwise to a mixture of tert-butyl (6-(((2S)-2-acetamidopropyl)oxy)-5-fluoropyridin-3-yl)carbamate (1.70 g) and THF (20 mL) at −78° C. under an argon atmosphere, and the obtained mixture was stirred at −78° C. for 1 hr. To the reaction mixture was added trimethyl borate (2.36 mL), the obtained mixture was allowed to warm to room temperature, and stirred at room temperature overnight. The reaction mixture was cooled to 0° C., and a mixture of 8M aqueous sodium hydroxide solution (2.60 mL) and aqueous hydrogen peroxide (30%, 5 mL) were added thereto. The obtained mixture was stirred at room temperature for 2 hr. To the reaction mixture was added saturated aqueous sodium thiosulfate solution at 0° C., and the mixture was acidified with 6M hydrochloric acid, and extracted with ethyl acetate. The combined organic layer were washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (0.541 g).

1. temperatureto warm to room temperature
2. stirringstirred at room temperature overnight
3. temperatureThe reaction mixture was cooled to 0° C.
4. additionwere added
5. stirringThe obtained mixture was stirred at room temperature for 2 hr
6. extractionextracted with ethyl acetate
7. washThe combined organic layer were washed with saturated brine
8. dry with materialdried over anhydrous magnesium sulfate
9. customthe solvent was evaporated under reduced pressure
10. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

ORD record

ord-aa4d2b9e08e94a18bf6d320863a9a599

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133129B2