Reacción #1924

Ecuación de reacción

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

Rendimiento 41.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaby heating
2. 2
   Temperaturaunder reflux for 2 hours
3. 3
   TemperaturaAfter the reaction mixture was cooled
4. 4
   Extracciónfollowed by extraction with ethyl acetate
5. 5
   LavadoThe organic layer was washed with a saturated aqueous solution of sodium chloride
6. 6
   Secadodried over anhydrous magnesium sulfate
7. 7
   FiltraciónAfter the drying agent was filtered off
8. 8
   Concentraciónthe organic layer was concentrated under reduced pressure
9. 9
   OtroThe obtained oily substance was purified by silica gel column chromatography (hexane/ethyl acetate=8/1)

Procedimiento

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%).

Fuente