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

Participants

Reaction Conditions

Reaction Steps

To a suspension of N-(4-{2-[4-(2-hydroxyethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide (552.5 mg, 1.799 mmol) in anhydrous tetrahydrofuran (8 ml) was added 1,1′-carbonyldiimidazole (437.8 mg, 2.700 mmol), and the mixture was stirred at 45° C. for 0.5 hr. tert-Butyl carbazate (356.8 mg, 2.700 mmol) was added. After stirring for 1 hr, tert-butyl carbazate (356.6 mg, 2.698 mmol) was added. After stirring for 3 hr, tert-butyl carbazate (357.0 mg, 2.701 mmol) was further added. After stirring for 24 hr, the mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. DM1025 60 g, ethyl acetate:hexane=5:5→7:3). The residue was further purified by silica gel column chromatography (Sep pak-5 g, ethyl acetate:hexane=7:3) to give 2-(4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}phenyl)ethyl tert-butyl hydrazine-1,2-dicarboxylate (755.9 mg, 1.685 mmol, yield 93.6%) as white crystals.

Provenance & Evidence