Lithium Hydroxide → 4-[2-Anilino-1-(anilinocarbonyl)-1-hydroxy-2-oxoethyl]benzoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoic acid in THF (5 mL) at room temperature was added a solution of LiOH (28 mg, 1.2 mmol) in water (2 mL). The reaction mixture was stirred open to air for 20 h then heated to 40° C. for 8 h. Additional LiOH (20 mg, 0.83 mmol) was added and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was diluted with ethyl acetate, washed with 1 M HCl (1×), brine (1×), dried over MgSO4, and concentrated. Purification by reverse phase HPLC (30% to 100% MeCN in water) gave 4-[2-anilino-1-(anilinocarbonyl)-1-hydroxy-2-oxoethyl]benzoic acid (31 mg, 25%) as a white solid: ESIMS calcd 391.1 (M++H), found 391.1 (M++H).

Provenance & Evidence