Water → 4-[2-({[2-(Tert-butoxycarbonyl)hydrazino]carbonyl}amino)ethyl]phenyl 2-(acetylamino)-1,3-thiazole-4-carboxylate

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Reaction Conditions

Reaction Steps

To a suspension of 2-(acetylamino)-1,3-thiazole-4-carboxylic acid (559.5 mg, 3.005 mmol) in anhydrous N,N-5 dimethylformamide (10 ml) was added 1,1′-carbonyldiimidazole (534.2 mg, 3.294 mmol), and the mixture was stirred at 50° C. for 2 hr. tert-Butyl 2-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}hydrazinecarboxylate (591.6 mg, 2.003 mmol) was added, and the mixture was stirred at 50° C. for 24 hr and at room temperature for 17 hr. Water (50 ml) and ethyl acetate (50 ml) were added to the reaction mixture and the mixture was stirred, stood still and then partitioned. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with 0.5M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Methanol (20 ml) and tert-butyl methyl ether (40 ml) were added to the residue and the precipitated solid was collected by filtration and dried under reduced pressure to give 4-[2-({[2-(tert-butoxycarbonyl)hydrazino]carbonyl}amino)ethyl]phenyl 2-(acetylamino)-1,3-thiazole-4-carboxylate (417.7 mg, 0.890 mmol, yield 44.5%) as a white solid.

Provenance & Evidence