Triethylamine → 1-[1-(2-toluoylmethyl)-2-oxo-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-methoxycarbonyl-4-chlorophenyl)urea

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Reaction Steps

Methyl 5-amino-2-chlorobenzoate (223 mg) was dissolved in tetrahydrofuran (50 ml), triphosgene (135 mg) was added under ice-cooling, triethylamine (116 μl) was added thereto five times every 3 minutes, the mixture was stirred for 10 minutes at same temperature. A solution of 1-(2-toluoylmethyl)-2-oxo-3-amino-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (500 mg) in tetrahydrofuran (10 ml) was added dropwise, the resultant mixture was stirred for 30 minutes at same temperature and additionally stirred for 2 hours at room temperature. The reaction mixture was poured into water (400 ml), extracted with methylene chloride. The organic layer was washed with 1N hydrochloric acid, dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography(n-hexane:ethyl acetate=2:1), to thereby obtain 756 mg of the titled compound.

Provenance & Evidence