Hydrogen chloride-ethyl acetate → HCID 67777389, compound

4M Hydrogen chloride/ethyl acetate (10 mL) was added dropwise to a solution of tert-butyl [(1S)-2-({6-[6-(cyclopropylmethoxy)-2,3-dihydro-1-benzofuran-2-yl]pyridin-3-yl}oxy)-1-methylethyl]carbamate (80 mg) in ethyl acetate (5 mL) at room temperature, and the reaction mixture was stirred at room temperature for 6 hr. The solvent was evaporated under reduced pressure, and the residue was dissolved in pyridine (10 mL), and acetic anhydride (0.026 mL) was added thereto at room temperature. The reaction mixture was stirred at room temperature for 2 hr, and the solvent was evaporated under reduced pressure. The residue was diluted with water, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with saturated sodium hydrogen carbonate and 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 (ethyl acetate/methanol) to give the title compound (49.3 mg).

1. customThe solvent was evaporated under reduced pressure
2. dissolutionthe residue was dissolved in pyridine (10 mL)
3. additionacetic anhydride (0.026 mL) was added
4. customat room temperature
5. stirringThe reaction mixture was stirred at room temperature for 2 hr
6. customthe solvent was evaporated under reduced pressure
7. additionThe residue was diluted with water
8. extractionthe mixture was extracted with ethyl acetate
9. washThe combined organic layer was washed with saturated sodium hydrogen carbonate and saturated brine
10. dry with materialdried over anhydrous magnesium sulfate
11. customthe solvent was evaporated under reduced pressure
12. customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol)

ORD record

ord-7d265b64d96740dd970c730b3b67abb8

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08729102B2