Acetone → 4-(2-Carboxypropan-2-ylamino)-2-fluorobenzoic acid

Participants

Reaction Conditions

Reaction Steps

4-Amino-2-fluoro-benzoic acid (0.2 g, 1.29 mmol) and 1,1,1-trichloro-2-methyl-propan-2-ol (0.593 g, 3.35 mmol) were dissolved in anhydrous acetone and the solution was cooled at 0° C. Powdered sodium hydroxide (0.2 g, 5.01 mmol) was added portion-wise after which the reaction mixture was warmed to and stirred at room temperature for 12 h. Volatiles were removed under reduced pressure and the residue was acidified with 1M aqueous HCl. The crude product obtained was purified by reverse phase HPLC to obtain 4-(1-carboxy-1-methyl-ethylamino)-2-fluoro-benzoic acid.

Provenance & Evidence