Reaktion #2066477

Reaktionsgleichung

2-bromo-2′-methylacetophenone

Sodium hydride

2-Oxo-3-tert-butoxycarbonylamino-5-pivaloyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

→

title compound

Ausbeute 79.0%

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

Ausbeute 79.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder ice-cooling
2. 2
   EinengenThe reaction mixture was concentrated under reduced pressure
3. 3
   workup.ADDITIONIce-water was added to the residue
4. 4
   ExtraktionThe resultant mixture was extracted with methylene chloride
5. 5
   WaschenThe organic layer was washed with saturated brine
6. 6
   Trocknendried over anhydrous sodium sulfate
7. 7
   Sonstigepurified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Vorschrift

60% Sodium hydride (1.6 g) was suspended in tetrahydrofuran (100 ml), 2-Oxo-3-tert-butoxycarbonylamino-5-pivaloyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (7.23 g) was added thereto under ice-cooling, and the resultant mixture was stirred for one hour. Subsequently, 2-bromo-2′-methylacetophenone (4.88 g) was added thereto, and 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. The resultant mixture was extracted with methylene chloride. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1), to thereby obtain 7.8 g of the title compound (yield: 79%)

Quelle