Potassium Permanganate → HCID 86671247, compound

Participants

Reaction Steps

To a solution of 2-[3-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-N-(4-chloro-5-formyl-thiazol-2-yl)-acetamide (590 mg, 1.436 mmol) in t-butanol (15 mL) stirred at 60° C. was added drop wise potassium permanganate (405 mg, 2.56 mmol) in water (5 mL) over 15 minutes. The resultant reaction mixture was heated at 80′C for 2 h. The reaction mixture was filtered hot through celite and washed with hot 1/1 t-butanol/water. The filtrate was acidified to pH 1 with aqueous 2N HCl and extracted with 9:1 Methylene chloride/methanol (3×75 mL). The organic layers were combined, washed with brine (50 mL), dried over MgSO4, filtered, concentrated under reduced pressure and dried to give 2-{2-[3-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-acetylamino}-4-chloro-thiazole-5-carboxylic acid (0.52 g, 84.8%) as a pale yellow solid. MS m/e 428.0 (M+H+).

Provenance & Evidence