Acetohydrazide → HCID 89610466, compound

Participants

Reaction Steps

HATU (739 mg, 1.94 mmol) was added to a solution of triethylammonium 3,4-bis(benzyloxy)-5-(ethoxycarbonyl)-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (5) (325 mg, 0.65 mmol), DIPEA (566 μL, 3.24 mmol) and acetohydrazide (53 mg, 0.71 mmol) in DMF (5 mL) at 0° C. The mixture was stirred for 30 min and allowed to warm to RT. The reaction was partitioned between water (10 mL) and Et2O (30 mL) and NH4OAc (aq.) (20 mL) was added, the organic layer was separated and washed with sat. NaHCO3 (aq.) (20 mL), brine (20 mL), dried (MgSO4), filtered and solvents removed in vacuo. The product was purified by silica gel chromatography (40 g, 0-80% EtOAc in isohexane) to afford ethyl 5-(2-acetylhydrazinecarbonyl)-3,4-bis(benzyloxy)-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (31) (196 mg, 100%) as a colourless oil: m/z 558 (M+H)+ (ES+).

Provenance & Evidence