Ammonium Chloride → 3-{5-[(4R,5S)-4,5-Dimethyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl]-5-{[(2S)-1-methoxypropan-2-yl]oxy}phenol

(4R,5S)-2-[5-(3-{[(2S)-1-Methoxypropan-2-yl]oxy}-5-[(tripropan-2-ylsilyl)oxy]phenyl)-1H-pyrrol-2-yl]-4,5-dimethyl-4,5-dihydro-1,3-oxazole (700 mg, 1.39 mmol) synthesized in Example (109b) was dissolved in tetrahydrofuran (10 mL), and tetrabutylammonium fluoride (1.0 mol/L tetrahydrofuran solution, 2.00 mL, 2.00 mmol) was added at room temperature, followed by stirring at room temperature for 30 minutes under nitrogen atmosphere. To this reaction solution, a saturated aqueous ammonium chloride solution (30 mL) was added, and extraction was carried out with methylene chloride (30 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=2%-3%) to afford the desired compound (420 mg, yield 88%) as a yellow liquid.

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=2%-3%)

ORD-Eintrag

ord-668ceca508a64d0c9d0d0449e1b3282a

Quelldatensatz

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08415359B2