Sodium Hydroxide → (S)-2-sec-Butylamino-6-(2-fluorophenyl)-isonicotinic acid

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Reaction Steps

Chill a solution of (S)-2-sec-butylamino-6-(2-fluorophenyl)-isonicotinic acid methyl ester (1.31 g, 4.32 mmol) in methanol (5 mL) and THF (5 mL). Add 2 N NaOH (6.50 mL, 13.0 mmol) stir at room temperature for 3 h, and acidify the solution to about pH=2 and concentrate to one half of the solvent. Partition the residue between ethyl acetate and water. Extract the aqueous layer with ethyl acetate (2×30 mL). Wash the combined organic extracts with saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give the title compound (80%).

Provenance & Evidence