Sodium Hydroxide → 2-(3-(1-(Tert-butoxycarbonyl)azetidin-3-ylcarbamoyl)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

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A mixture of methyl 2-(3-(1-(tert-butoxycarbonyl)azetidin-3-ylcarbamoyl)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (234 mg, 0.44 mmol of theory) in methanol (6.8 mL) and 1 M sodium hydroxide aqueous solution (5.3 mL, 5.3 mmol, 12.0 eq.) was heated to reflux for 60 min, LC-MS showed the reaction was complete and only the desired product formed. The solvent was concentrate in vacuo and the residue was dissolved in water and acidified with 1 M hydrochloric acid solution to pH=6. The white precipitated solid was extracted with tetrahydrofuran (twice). The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate. Removal of the solvent gave 209 mg product as a white solid, which was purified by column chromatography (Pure ethyl acetate) to afford 78 mg of 2-(3-(1-(tert-butoxycarbonyl)azetidin-3-ylcarbamoyl)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a white solid. Yield: 37.2%. MS (ESI+APCI) M+1=480.2.

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