반응 #1924

반응 방정식

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

수율 41.0%

반응 조건

후처리

1. 1
   온도by heating
2. 2
   온도under reflux for 2 hours
3. 3
   온도After the reaction mixture was cooled
4. 4
   추출followed by extraction with ethyl acetate
5. 5
   세척The organic layer was washed with a saturated aqueous solution of sodium chloride
6. 6
   건조dried over anhydrous magnesium sulfate
7. 7
   여과After the drying agent was filtered off
8. 8
   농축the organic layer was concentrated under reduced pressure
9. 9
   기타The obtained oily substance was purified by silica gel column chromatography (hexane/ethyl acetate=8/1)

실험 절차

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%).

출처