Triethylamine → (+)-1-(1-tert-butylcarbonylmethyl-2-oxo-5-phenyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-benzyloxycarbonylphenyl)urea

温度

60 °C

Diphenylphosphoryl azide (1.38 g) and triethylamine (0.77 ml) were added to a solution of isophthalic acid benzyl ester (1.15 g) in anhydrous dioxane (20 ml), the mixture was stirred at 60° C. for 30 minutes and subsequently stirred at internal temperature 80° C. for one hour. The reaction mixture was allowed to come to room temperature, a solution of (+)-1-tert-butylcarbonylmethyl-2-oxo-3-amino-5-phenyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (1.1 g) in anhydrous dioxane (20 ml) was added thereto, the mixture was stirred for 2 hours at room temperature. The resultant mixture was concentrated under reduced pressure, chloroform was added, the mixture was washed succesively with saturated aqueous sodium bicarbonate and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography(n-hexane:ethyl acetate=2:1), to thereby obtain 622 mg of the titled compound.

1. stirringsubsequently stirred at internal temperature 80° C. for one hour
2. customto come to room temperature
3. stirringthe mixture was stirred for 2 hours at room temperature
4. concentrationThe resultant mixture was concentrated under reduced pressure, chloroform
5. additionwas added
6. washthe mixture was washed succesively with saturated aqueous sodium bicarbonate and saturated brine
7. dry with materialdried over anhydrous sodium sulfate
8. customThe solvent was evaporated under reduced pressure
9. customthe residue was purified by silica gel column chromatography(n-hexane:ethyl acetate=2:1)

ORDレコード

ord-ec68c643517b423cb24042cb6442717c

出典データセット

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06239131B1