Lithium Hydroxide → HCID 16074694, compound

Participants

Reaction Steps

3-[(2,4-Dichloro-benzoyl)-phenyl-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester (55 mg, 0.11 mmol) was dissolved in a mixture of THF-MeOH—H2O (3:2:1) (15 mL) and then 0.66 ml of LiOH 1N was added to it. After 60 min of stirring at room-temperature, solvents were removed and then partitioned between 15 ml of H2O, 4 ml of KHSO4 5% and 15 ml of EtOAc. The organic layer was separated and the aqueous phase was washed twice with ethyl acetate (2×10 mL). The combined ethyl acetate layer was dried (MgSO4), concentrated and the residue was purified by preparative chromatography (10% MeOH/CH2Cl2) to obtain 32 mg (60%) of 3-[(2,4-Dichloro-benzoyl)-phenyl-amino]-5-phenyl-thiophene-2-carboxylic acid. NMR 1H (DMSO, 400 MHz): Rotamer: 7.75 ppm (d, 1H, Haro); 7.68 ppm (2H, Haro); 7.53 ppm (d, Haro, minor rotamer); 7.51-7.23 ppm (m, 11H, Haro, minor rotamer); 7.17 ppm (Haro, minor rotamer).

Provenance & Evidence