Hydrochloric Acid → 2-Methyl-2-({2-methyl-4-[(1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}pentyl)oxy]phenyl}oxy)propanoic acid

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Reaction Steps

Ethyl 2-methyl-2-({2-methyl-4-[(1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}pentyl)oxy]phenyl}oxy)propanoate (9 mg, 0.02 mmol) was dissolved in THF (0.75 mL), water (0.25 mL) and aqueous NaOH (2M, 35 μl, 0.07 mmol) and the mixture heated at 80° C. for 16 hours. More aqueous NaOH (2M, 420 μl, 0.84 mmol) was then added and heating continued for an additional 24 hours. The mixture was then cooled, neutralised with aqueous HCl (2M), partitioned between EtOAc and water and the layers separated. The organic layer was then washed with brine, dried (Na2SO4) and reduced to give a pale yellow oil. Purification by SPE (aminopropyl, 1 g cartridge) loading in CHCl3 and eluting with dioxane and then 10% aqueous ammonia in dioxane afforded the title compound as a colourless gum (4.5 mg).

Provenance & Evidence