Sodium Hydroxide → (6-(5-{3-Cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2-{[(1,1-dimethylethyl)oxy]carbonyl}-5-methyl-1,2,3,4-tetrahydro-1-isoquinolinyl)acetic acid

Participants

Reaction Steps

To a solution of 1,1-dimethylethyl 1-[2-(butyloxy)-2-oxoethyl]-6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1h)-isoquinolinecarboxylate (Preparation 21; 41 mg, 0.070 mmol) in ethanol (2 ml) was added 2N aqueous sodium hydroxide (0.070 ml, 0.139 mmol) and the resulting mixture was stirred at room temperature for ca. 3.5 h. Most of the solvent was removed and the residue was partitioned between ether and water (with dropwise addition of 2N sodium hydroxide to keep the mixture basic). The layers were separated, and the aqueous layer acidified 2N aqueous hydrochloric acid giving a white precipitate which was extracted twice with ethyl acetate. The combined ethyl acetate fractions were dried over MgSO4 and concentrated in vacuo to give the title compound (38 mg).

Provenance & Evidence