Hydrochloric Acid → 1-[1-(2-Toluoylmethyl)-2-oxo-5-benzyloxycarbonyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-ethoxycarbonylphenyl)urea

Participants

Reaction Steps

Ethyl 3-aminobenzoate (4.29 g) was dissolved in tetrahydrofuran (600 ml), triphosgene (2.54 g) was added under ice-cooling, triethylamine (2.19 ml) was added thereto five times every 3 minutes after divided into five portions. A solution of 1-(2-toluoylmethyl)-2-oxo-3-amino-5-benzyloxycarbonyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (9.78 g) in tetrahydrofuran (200 ml) was added, the mixture was stirred for 30 minutes, subsequently, stirred overnight at room temperature. The reaction mixture was poured into water (3 L), acidified with 1N hydrochloric acid, extracted with methylene chloride. The organic layer was washed with saturated aqueous sodium bicarbonate, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography(chloroform:ethyl acetate=2:1), to thereby obtain 13.3 g of the titled compound.

Provenance & Evidence