Ethyl Acetate → 3,3-Dimethyl-2-(3-(methylsulfonylcarbamoyl)-phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

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Reaction Steps

A mixture of methyl 3,3-dimethyl-2-(3-(methylsulfonylcarbamoyl)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate (58 mg, 0.14 mmol, 1.0 eq.) in methanol (2.5 mL) and 1N sodium hydroxide aqueous solution (2.1 mL, 2.1 mmol, 15.0 eq.) was heated to reflux for 1 h. Thin layer chromatography (petroleum ether:ethyl acetate=1:1) and LC-MS showed the reaction was complete. The reaction mixture was concentrated under reduced pressure and the residual was acidified with 1N hydrochloric acid solution to pH=5. The white solid precipitated was dissolved in ethyl acetate and separated. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate Removal of the solvent in vacuo gave 56 mg of 3,3-dimethyl-2-(3-(methylsulfonylcarbamoyl)-phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a yellow solid in quantitative yield. MS (ESI+APCI) M+1=403.1.

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