Triethylamine → HCID 21201974, compound

Participants

Reaction Steps

Ethyl 3-aminobenzoate (340 mg) was dissolved in anhydrous tetrahydrofuran (50 ml), triphosgene (228 mg) was added, triethylamine (0.9 ml) was added thereto five times after divided into five portions over 15 minutes at 0° C., and the mixture was stirred at room temperature for 5 minutes. To this solution was added a solution of 1-tert-butylcarbonylmethyl-2-oxo-3-amino-5-pivaloyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine that obtained from Step 2 in tetrahydrofuran (10 ml), the resultant mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, water was added, and the mixture was extracted with methylene chloride. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1), to thereby obtain 870 mg of the titled compound (Yield: 79%).

Provenance & Evidence