Methanol → 3-phenyl-2-[(6-{5-phenyl-1-[4-(trifluoromethyl)benzyl]-1H-pyrrol-2-yl}-2-naphthyl)oxy]propanoic acid

Participants

Reaction Conditions

Reaction Steps

In a similar manner as described in step 2 of Example 6, the title compound was prepared from methyl 3-phenyl-2-[(6-{5-phenyl-1-[4-(trifluoromethyl)benzyl]-1H-pyrrol-2-yl}-2-naphthyl)oxy]propanoate (0.200 g, 0.330 mmol), prepared in the previous step, and 1N NaOH (0.50 mL, 0.50 mmol) in 1.33:1.33:1 THF:MeOH:water (33 mL) with the exception that this reaction was not complete after 18 hours (overnight) at ambient temperature. The reaction was warmed to 30° C. for 1.5 hours, an additional portion of 1N NaOH (0.50 mL, 0.50 mmol) was added and the mixture maintained at 30° C. for an additional 1.5 hours. The isolated yellow amorphous solid was purified by reverse-phase (C18) HPLC using 20% water in acetonitrile with 0.1% formic acid as the eluent. Isolation of the product from the chromatography fractions gave 3-phenyl-2-[(6-{5-phenyl-1-[4-(trifluoromethyl)benzyl]-1H-pyrrol-2-yl}-2-naphthyl)oxy]propanoic acid as a greenish amorphous solid (0.139 g, 71%), mp 153–155° C. Elemental Analysis for C37H28F3NO3.0.24 H2O.0.10 C6H14 Calc'd: C, 74.70; H, 4.98; N, 2.32. Found: C, 74.67; H, 5.23; N, 2.25.

Provenance & Evidence