Triethylamine → (R)-(-)-1-(2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-tert-butoxycarbonylphenyl)urea

Beteiligte Stoffe

Reaktionsschritte

Triphosgene (1.8 g) was added to a solution of tert-butyl 3-aminobenzoate (3.13 g) in anhydrous tetrahydrofuran (200 ml) under ice-cooling, and then triethylamine (7.25 ml) was added five times each 1.45 ml over 15 minutes, and the mixture was stirred at room temperature for 5 minutes. Subsequently (R)-(−)-2-oxo-3-amino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (4 g) was added under ice-cooling. The mixture was stirred at room temperature for one hour, the reaction mixture was concentrated under reduced pressure. Ice-water was added to the residue, extracted with methylene chloride,the organic layer was washed with saturated brine. After dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the residue, crystals were collected by filtration, to thereby obtain 7.38 g of the titled compound.

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