Hydrochloric Acid → Methyl N-[(5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrol-2-yl)carbonyl]glycinate

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Reaction Steps

5-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrole-2-carboxylic acid (275 mg, 0.617 mmol) synthesized in Example (18a) was dissolved in dichloromethane (10 mL), and glycine methyl ester hydrochloride (120 mg, 0.956 mmol), WSCI.HCl (180 mg, 0.939 mmol) and 4-dimethylaminopyridine (150 mg, 1.23 mmol) were added, followed by stirring at room temperature for 2 hours under nitrogen atmosphere. 1N hydrochloric acid (10 mL) was added, and the solution was separated with dichloromethane (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=20%-60%) to afford the desired product (270 mg, yield 85%) as a white solid.

Provenance & Evidence