Water → 2-[4-({[2-(Acetylamino)-1,3-thiazol-4-yl]carbonyl}oxy)phenyl]ethyl tert-butyl hydrazine-1,2-dicarboxylate

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Reaction Conditions

Reaction Steps

To a suspension of 2-(acetylamino)-1,3-thiazole-4-carboxylic acid (466.2 mg, 2.504 mmol) in anhydrous N,N-dimethylformamide (5 ml) was added 1,1′-carbonyldiimidazole (405.7 mg, 2.502 mmol), and the mixture was stirred at 50° C. for 2.5 hr. tert-Butyl 2-(4-hydroxyphenyl)ethyl hydrazine-1,2-dicarboxylate (594.8 mg, 2.001 mmol) was added, and the mixture was stirred at 50° C. for 18 hr. Water (40 ml) and ethyl acetate (40 ml) were added to the reaction mixture and the mixture was stirred, stood still and then partitioned. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 40 g, hexane:ethyl acetate=6:4→5:5). The fractions containing the object product were concentrated under reduced pressure and the obtained solid was suspended in a mixture of hexane (40 ml) and tert-butyl methyl ether (20 ml). The suspension was filtered and dried under reduced pressure to give 2-[4-({[2-(acetylamino)-1,3-thiazol-4-yl]carbonyl}oxy)phenyl]ethyl tert-butyl hydrazine-1,2-dicarboxylate (539.2 mg, 1.161 mmol, yield 58.0%) as a white solid.

Provenance & Evidence