反応 #1924

反応方程式

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

収率 41.0%

反応条件

後処理

1. 1
   温度by heating
2. 2
   温度under reflux for 2 hours
3. 3
   温度After the reaction mixture was cooled
4. 4
   抽出followed by extraction with ethyl acetate
5. 5
   洗浄The organic layer was washed with a saturated aqueous solution of sodium chloride
6. 6
   乾燥dried over anhydrous magnesium sulfate
7. 7
   ろ過After the drying agent was filtered off
8. 8
   濃縮the organic layer was concentrated under reduced pressure
9. 9
   その他The obtained oily substance was purified by silica gel column chromatography (hexane/ethyl acetate=8/1)

実験手順

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%).

出典