Реакция #1924

Уравнение реакции

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

Выход 41.0%

Условия реакции

Обработка

1. 1
   Температураby heating
2. 2
   Температураunder reflux for 2 hours
3. 3
   ТемператураAfter the reaction mixture was cooled
4. 4
   Экстракцияfollowed by extraction with ethyl acetate
5. 5
   ПромывкаThe organic layer was washed with a saturated aqueous solution of sodium chloride
6. 6
   Сушкаdried over anhydrous magnesium sulfate
7. 7
   ФильтрацияAfter the drying agent was filtered off
8. 8
   Концентрированиеthe organic layer was concentrated under reduced pressure
9. 9
   ДругоеThe obtained oily substance was purified by silica gel column chromatography (hexane/ethyl acetate=8/1)

Методика

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%).

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