Reaktion #1924

Reaktionsgleichung

diphenylphosphoryl azide

2-carboxy-6,11-dihydrodibenz-[b,e]oxepin-11-one

triethylamine

tert-butanol

sodium bicarbonate

→

2-tert-butoxycarbonylamino-6,11-dihydrodibenz[b,e]oxepin-11-one

Ausbeute 41.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturby heating
2. 2
   Temperaturunder reflux for 2 hours
3. 3
   TemperaturAfter the reaction mixture was cooled
4. 4
   Extraktionfollowed by extraction with ethyl acetate
5. 5
   WaschenThe organic layer was washed with a saturated aqueous solution of sodium chloride
6. 6
   Trocknendried over anhydrous magnesium sulfate
7. 7
   FiltrationAfter the drying agent was filtered off
8. 8
   Einengenthe organic layer was concentrated under reduced pressure
9. 9
   SonstigeThe obtained oily substance was purified by silica gel column chromatography (hexane/ethyl acetate=8/1)

Vorschrift

To tert-butanol (8.3 ml) were added diphenylphosphoryl azide (1.1 ml, 5.11 mmol), 2-carboxy-6,11-dihydrodibenz-[b,e]oxepin-11-one (Japanese Published Unexamined Patent Application No. 91040/90) (1.0 g, 3.9 mmol), and triethylamine (0.71 ml, 5.11 mmol) under an atmosphere of argon gas, followed by heating under reflux for 2 hours. After the reaction mixture was cooled, it was poured into a 5% aqueous solution of sodium bicarbonate, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The obtained oily substance was purified by silica gel column chromatography (hexane/ethyl acetate=8/1), followed by trituration with hexane to give 2-tert-butoxycarbonylamino-6,11-dihydrodibenz[b,e]oxepin-11-one as a white solid (0.51 g, 41%).

Quelle