Triethylamine → HCID 70792365, compound

Participants

Reaction Steps

To a stirred solution of 0.06 g of N-BOC-glycine (CAS 4530-20-5) (0.34 mmol; 1.2 eq.) in 1 mL of N,N′-dimethylformamide are added 0.16 g of 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (0.43 mmol; 1.5 eq.) and 0.1 mL of triethylamine (0.71 mmol; 2.5 eq.) at room temperature. After stirring for 0.5 h at room temperature, a solution of 0.1 g of 2-[2-(4-amino-furazan-3-yl)-benzoimidazol-1-yl]-1-(4-amino-phenyl)-ethanone (CAS 798577-83-0) (0.28 mmol; 1 eq.) in 1 mL of N,N′-dimethylformamide is added. The reaction solution is stirred overnight at room temperature. Then, a solution of 0.03 g of N-BOC-glycine (0.17 mmol; 0.6 eq.) containing 0.08 g of 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU) (0.22 mmol; 0.75 eq.) and 0.05 mL of triethylamine (0.35 mmol; 1.25 eq.) in 0.5 mL of N,N′-dimethylformamide is added to the reaction solution at room temperature. The same mixture is added again after additional 24 h and additional 8 h. The reaction mixture is then further stirred for 64 h (total reaction time 120 h). The reaction mixture is diluted with ethyl acetate (10 mL) and then washed with water (10 mL), 10% citric acid aqueous solution (10 mL), brine (2×5 mL), dried over magnesium sulfate, filtered and concentrated to dryness to give crude product. The crude product is subjected to silica gel column chromatography (eluent: ethyl acetate/cyclohexane=1/1 to 4/1). The obtained material is recrystallized from dichloromethane to afford 0.085 g of the desired product as a white powder.

Provenance & Evidence