Methanol → [(6-{5-Phenyl-1-[4-(trifluoromethyl)benzyl]-1H-pyrrol-2-yl}-2-naphthyl)oxy]acetic acid

Participants

Reaction Steps

In a similar manner as described in step 2 of Example 6, the title compound was prepared from methyl [(6-{5-phenyl-1-[4-(trifluoromethyl)benzyl]-1H-pyrrol-2-yl}-2-naphthyl)oxy]acetate (0.20 g, 0.38 mmol), prepared in the previous step, and 1N NaOH (0.58 mL, 0.58 mmol) in 1.67:1.67:1 THF:MeOH:water (39 mL). Purification on a Biotage Horizon™ system with a KP-Sil Flash 25+M column (40 g Silica Gel, 60 Å) using 25% EtOAc in hexane with 1% formic acid as the eluent gave [(6-{5-phenyl-1-[4-(trifluoromethyl)benzyl]-1H-pyrrol-2-yl}-2-naphthyl)oxy]acetic acid as an off-white solid (0.155 g, 79%), mp 154–156° C. Elemental Analysis for C30H22F3NO3.0.02 H2O Calc'd: C, 71.80; H, 4.43; N, 2.79. Found: C, 71.96; H, 4.55; N, 2.61.

Provenance & Evidence