Hydrochloric Acid → N-[(2S)-2-Hydroxypropyl]-5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrole-2-carboxamide

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Reaction Steps

5-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrole-2-carboxylic acid (305 mg, 0.685 mmol) synthesized in Example (18a) was dissolved in dichloromethane (10 mL), and (S)-(+)-1-amino-2-propanol (110 μmL, 1.40 mmol), WSCI.HCl (200 mg, 1.04 mmol) and 4-dimethylaminopyridine (170 mg, 1.39 mmol) were added, followed by stirring at room temperature for 16 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=60%-100%) to afford the desired product (285 mg, yield 83%) as a white solid.

Provenance & Evidence