Hydrochloric Acid → 2-Fluoro-4-[(1,3-thiazol-2-ylamino)sulfonyl]benzoic acid

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Reaction Steps

A mixture of methyl 4-{[(2,4-dimethoxybenzyl)(1,3-thiazol-2-yl)amino]sulfonyl}-2-fluorobenzoate (Preparation 14, 10 g, 21 mmol, 1 eq) and sodium hydroxide 4.3 g, 0.107 mol, 5 eq) in THF: MeOH: water (25 ml:2 ml:75 ml) was heated at 50° C. for 4 hours. The reaction mixture was acidified to pH 2.0 with 2M HCl and the resulting precipitate collected by filtration. The crude material was purified by column chromatography eluting with 90:10:1 DCM: MeOH: ammonia to yield the title compound as a yellow solid (706 mg, 2.33 mmol, 11%).

Provenance & Evidence