Reaktion #2066504

Reaktionsgleichung

Diphenylphosphoryl azide

triethylamine

isophthalic acid mono-benzyl ester

1-tert-butylcarbonylmethyl-2-oxo-3-amino-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

→

title compound

Ausbeute 54.0%

1-(1-tert-butylcarbonylmethyl-2-oxo-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-benzyloxycarbonylphenyl)urea

Ausbeute 54.0%

Lösungsmittel

dioxane

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITinternal temperature at 80° C. for 2 hours
2. 2
   Temperaturto cool to room temperature
3. 3
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 30 minutes
4. 4
   EinengenThe mixture was concentrated under reduced pressure, chloroform (50 ml)
5. 5
   workup.ADDITIONwas added to the resultant residue
6. 6
   Waschenwashed with saturated aqueous sodium bicarbonate
7. 7
   TrocknenAfter dried over anhydrous sodium sulfate
8. 8
   Sonstigethe solvent was evaporated under reduced pressure
9. 9
   workup.ADDITIONthe mixed solvent of isopropyl ether and ethyl acetate was added to the residue for trituration

Vorschrift

Diphenylphosphoryl azide (1.1 g) and triethylamine (0.62 ml) were added to a solution of isophthalic acid mono-benzyl ester (792 mg) in dioxane (20 ml), the mixture was stirred internal temperature at 60° C. for 20 minutes and internal temperature at 80° C. for 2 hours. After the reaction mixture was allowed to cool to room temperature, a solution of 1-tert-butylcarbonylmethyl-2-oxo-3-amino-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (723 mg) obtained from Step 1 of Example 33 in dioxane (5 ml) was added to the reaction mixture. The reaction mixture was stirred at room temperature for 30 minutes. The mixture was concentrated under reduced pressure, chloroform (50 ml) was added to the resultant residue, and washed with saturated aqueous sodium bicarbonate. After dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, the mixed solvent of isopropyl ether and ethyl acetate was added to the residue for trituration, to thereby obtain 674 mg of the title compound as a colorless solid (Yield: 54%).

Quelle