Ethyl Acetate → 2-(4-{2-[2-(Acetylamino)-1,3-thiazol-4-yl]ethyl}phenyl)ethyl hydrazinecarboxylate hydrochloride

Participants

Reaction Steps

To a suspension of 2-(4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}phenyl)ethyl tert-butyl hydrazine-1,2-dicarboxylate (620.0 mg, 1.382 mmol) in anhydrous dichloromethane (6.9 ml) was added 4M hydrogen chloride dioxane solution (6.9 ml, 27.6 mmol). After stirring at room temperature for 13 hr, the reaction mixture was concentrated under reduced pressure. Dichloromethane was added to the residue, and the mixture was concentrated again under reduced pressure. The operation was performed twice. Ethyl acetate was further added to the residue, and the mixture was concentrated under reduced pressure. This operation was performed 3 times to remove hydrogen chloride gas azeotropically. The residue was dried under reduced pressure to give a crude product (570.4 mg). The crude product was dissolved in methanol (18 ml) and ethyl acetate (144 ml) was added to recrystallize the crude product. The crystals were collected by filtration, washed with ethyl acetate, and dried under reduced pressure to give the title compound (474.8 mg, 1.234 mmol, yield 89.3%) as a white solid.

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