2,6-Lutidine → HCID 59225852, compound

Participants

Reaction Steps

Glycine ethyl ester hydrochloride (76 mg, 0.541 mmol, 1.2 equiv.), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (130 mg, 0.676 mmol, 1.5 equiv.), 1-hydroxy-7-azabenzotriazole (92 mg, 0.676 mmol, 1.5 equiv.) and 2,6-lutidine (0.16 mL, 1.35 mmol, 3.0 equiv) were added to a solution of 2-(5-bromo-1-(4-cyanonaphthalen-l-yl)-1H-imidazol-2-ylthio)acetic acid (175 mg, 0.451 mmol) in dichloromethane (2.25 mL) and stirred at room temperature for 18 hours. The crude product was purified by SGC (0-100% ethyl acetate/hexanes) to afford the title compound containing some 1-hydroxy-7-azabenzotriazole. The impure product was dissolved in ethyl acetate (50 mL), washed with aqueous HCl solution (0.1M, 2×30 mL), saturated aqueous NaHCO3 solution (30 mL), and saturated sodium chloride solution (30 mL). The organics were dried over sodium sulfate, filtered, and concentrated to afford ethyl 2-(2-(5-bromo-1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)acetamido)acetate as a yellow oil (199 mg, 93%).

Provenance & Evidence