Reaktion #2066482

Reaktionsgleichung

HCl dioxane

1-(2-toluoylmethyl)-2-oxo-3-tert-butoxycarbonylamino-5-(adamantan-1-yl)carbonyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

→

title compound

Ausbeute 93.1%

1-[1-(2-toluoylmethyl)-2-oxo-5-(adamantan-1-yl)carbonyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-methylphenyl)urea

Ausbeute 93.1%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium bicarbonate
2. 2
   workup.ADDITIONwas added to the residue
3. 3
   Extraktionfollowed by extraction with methylene chloride
4. 4
   TrocknenThe organic layer was dried over anhydrous sodium sulfate
5. 5
   Sonstigethe solvent was evaporated under reduced pressure
6. 6
   workup.DISSOLUTIONSubsequently, this compound was dissolved in anhydrous tetrahydrofuran (10 ml)
7. 7
   workup.ADDITIONm-tolyl isocyanate (0.10 ml) was added to thereto
8. 8
   workup.STIRRINGThe mixture was stirred at room temperature for 15 minutes
9. 9
   SonstigeThe solvent was evaporated under reduced pressure
10. 10
    workup.ADDITIONA solvent mixture of isopropyl ether and ethanol
11. 11
    workup.ADDITIONwas added
12. 12
    Sonstigefor solidification and collection
13. 13
    Filtrationby filtration

Vorschrift

4N HCl-dioxane (5.0 ml) was added to 1-(2-toluoylmethyl)-2-oxo-3-tert-butoxycarbonylamino-5-(adamantan-1-yl)carbonyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (400 mg) in anhydrous ethanol (15 ml), and the mixture was stirred at 50° C. for 15 minutes. The reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium bicarbonate was added to the residue, followed by extraction with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure, to thereby obtain 1-(2-toluoylmethyl)-2-oxo-3-amino-5-(adamantan-1-yl)carbonyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine. Subsequently, this compound was dissolved in anhydrous tetrahydrofuran (10 ml), and m-tolyl isocyanate (0.10 ml) was added to thereto. The mixture was stirred at room temperature for 15 minutes. The solvent was evaporated under reduced pressure. A solvent mixture of isopropyl ether and ethanol was added thereto for solidification and collection by filtration, to thereby obtain 394 mg of the title compound (yield: 93.1%).

Quelle