Carbon Tetrachloride → 5-Methoxy-2-(5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrol-2-yl)-1,3-oxazole

Participants

Reaction Steps

Methyl N-[(5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrol-2-yl)carbonyl]glycinate (270 mg, 0.523 mmol) synthesized in Example (24a) was dissolved in acetonitrile (10 mL), and triphenylphosphine (410 mg, 1.56 mmol), triethylamine (0.22 mL, 1.58 mmol) and carbon tetrachloride (0.33 mL, 3.42 mmol) were added, followed by stirring at room temperature for 15 hours under nitrogen atmosphere. Water (10 mL) was added, and the solution was separated with ethyl acetate (15 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: ethyl acetate/hexane=10%-40%) to afford the desired product (162 mg, yield 62%) as an orange solid.

Provenance & Evidence