1,1'-Carbonyldiimidazole → HCID 86649981, compound

Participants

Reaction Steps

To a suspension of N-(4-{2-[4-(hydroxymethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide (161.5 mg, 0.584 mmol) in anhydrous tetrahydrofuran (2.4 ml) was added 1,1′-carbonyldiimidazole (142.1 mg, 0.876 mmol), and the mixture was stirred at room temperature for 1.5 hr. tert-Butyl carbazate (115.9 mg, 0.877 mmol) was added, and the mixture was stirred for 16 hr. tert-Butyl carbazate (77.3 mg, 0.584 mmol) was added, and the mixture was stirred for 4 hr. tert-Butyl carbazate (77.3 mg, 0.584 mmol) was added again, and the mixture was stirred for 2 hr. tert-Butyl carbazate (115.9 mg, 0.877 mmol) was added again, and the mixture was stirred for 4 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 10 g, ethyl acetate:hexane=5:5→6:4→7:3). The residue was further purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. DM2035 5 g, ethyl acetate:hexane=5:5→1:0) to give 4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}benzyl tert-butyl hydrazine-1,2-dicarboxylate (207.0 mg, 0.476 mmol, yield 81.6%) as a white solid.

Provenance & Evidence