Sodium Hydroxide → 4-(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)butanoic acid

Participants

Reaction Steps

To a solution of 1,1-dimethylethyl 6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-[4-(ethyloxy)-4-oxobutyl]-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Preparation 29; 111 mg, 0.189 mmol) in ethanol (5 ml) was added 2M aqueous sodium hydroxide (0.189 ml, 0.377 mmol) and the resulting mixture was stirred at room temperature for 3 h. More 2M aqueous sodium hydroxide (2 equivalents) was added, and stirring was continued at room temperature for a further 3 h. Most of the solvent was removed and the residue partitioned between ethyl acetate and water. The aqueous layer was acidified with 2N aqueous hydrochloric acid, the layers separated, and the aqueous layer further extracted with ethyl acetate. The combined organic layers were dried over MgSO4 and concentrated in vacuo to give the title compound (102 mg) as a white foam.

Provenance & Evidence