Sodium Hydroxide → 5-n-Butyl-4-(4-carboxybenzyl)-2,4-dihydro-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one

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Reaction Conditions

Reaction Steps

A solution of 25 mg (0.0577 mmole) of 5-n-butyl-2,4-dihydro-4-[4-(methoxycarbonyl)benzyl]-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one (from Example 26) in 0.25 mL of THF was treated with 0.25 mL of 1N sodium hydroxide in methanol, and the resulting solution was stirred overnight at 60° C. Volatiles were removed by evaporation, and the residue was taken up in 1 mL of methanol and acidified to pH 1.5 by addition of 1N HCl in methanol. The mixture was concentrated to dryness. The residue was leached with chloroform. The CHCl3 solution was dried over anhydrous sodium sulfate, filtered through Celite, and concentrated in vacuo to give 23 mg (96%) of the title compound as a colorless, glassy solid; homogeneous by TLC in 9:1 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 420 (M+1)+.

Provenance & Evidence