Sodium Hydroxide → 2-(4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)acetic acid

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Reaction Steps

To a solution of ethyl {4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]phenyl}acetate (for a preparation, see Intermediate 61) (270 mg, 0.597 mmol) in methanol (6 mL) and water (2 mL) at room temperature was added sodium hydroxide (2N in water, 0.597 mL, 1.193 mmol) and the resulting mixture was stirred at this temperature for 6 h. 0.5 ml of 2N sodium hydroxide in water were then added and the resulting mixture was left standing for 16 h. Most of the methanol was then removed in vacuo and the residue was partitioned between water and Et2O. The layers were separated. The aqueous layer was acidified with 2 mL of 2N HCl in water and extracted twice with AcOEt. The combined AcOEt fractions were dried over MgSO4 and concentrated in vacuo to give {4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]phenyl}acetic acid (200 mg, 0.471 mmol, 79% yield) as a brown foam.

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