Sodium Hydroxide → (2S)-2-(3-{5-[(4R)-4-Ethyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl]-5-{[5-(methylsulfonyl)pyrazin-2-yl]oxy}phenoxy)propan-1-ol

2-(3-{5-[(4R)-4-Ethyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}-5-{[(2S)-1-methoxypropan-2-yl]oxy}phenoxy)-5-(methylsulfonyl)pyrazine (417 mg, 0.83 mmol) synthesized in Example (108c) was dissolved in methylene chloride (10 mL), and boron tribromide (1.0 mol/L methylene chloride solution, 1.00 mL, 1.00 mmol) was added dropwise at −78° C., followed by stirring at room temperature for 1 hour under nitrogen atmosphere. To this reaction solution, a 1N aqueous sodium hydroxide solution (20 mL) was added, and extraction was carried out with methylene chloride (20 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: methanol/methylene chloride=3%-4%) to afford the desired compound (325 mg, yield 80%) as a white solid.

1. extractionextraction
2. washThe organic layer was washed with saturated brine
3. dry with materialsubsequently dried over anhydrous magnesium sulfate
4. distillationThe solvent was distilled off under reduced pressure
5. customthe resulting residue was purified
6. washsilica gel column chromatography (elution solvent: methanol/methylene chloride=3%-4%)

ORD record

ord-04d5bf9b23d841bd9bcddd3a78eb19bf

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08017610B2