Hydrogen chloride-ethyl acetate → HCID 86731204, compound

To tert-butyl ((2S)-1-((2-(4-(cyclopropylmethoxy)phenyl)-1H-benzimidazol-6-yl)oxy)propan-2-yl)carbamate (901 mg) was added 4 M hydrogen chloride/ethyl acetate (10 mL), and the mixture was stirred at room temperature for 20 min, and concentrated. To the residue were added pyridine (10 mL) and acetic anhydride (10 mL), and the mixture was stirred at room temperature for 15 min, and concentrated. The residue was dissolved in methanol (10 mL) and THF (10 mL), and saturated aqueous sodium hydrogen carbonate solution (10 mL) was added thereto, and the mixture was stirred at room temperature for 30 min. The reaction mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to give the title compound (490 mg).

1. concentrationconcentrated
2. additionTo the residue were added pyridine (10 mL) and acetic anhydride (10 mL)
3. stirringthe mixture was stirred at room temperature for 15 min
4. concentrationconcentrated
5. dissolutionThe residue was dissolved in methanol (10 mL)
6. additionTHF (10 mL), and saturated aqueous sodium hydrogen carbonate solution (10 mL) was added
7. stirringthe mixture was stirred at room temperature for 30 min
8. extractionThe reaction mixture was extracted with ethyl acetate
9. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
10. customThe solvent was evaporated under reduced pressure
11. customthe obtained residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)

ORD record

ord-05fd6c24b5e34188a58abb807f39d9e3

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133129B2