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

HRID 1828

Reaktionsgleichung

Reaktionsgleichung von HRID 1828
C1(P([N:15]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C([C:21]1[CH:36]=[CH:35][C:24]2[O:25][CH2:26][C:27]3[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=3[C:29](=[O:30])[C:23]=2[CH:22]=1)(O)=O.C(N(CC)CC)C.[C:44](=[O:47])(O)[O-:45].[Na+].[C:49](O)([CH3:52])([CH3:51])[CH3:50]>>[C:49]([O:45][C:44]([NH:15][C:21]1[CH:36]=[CH:35][C:24]2[O:25][CH2:26][C:27]3[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=3[C:29](=[O:30])[C:23]=2[CH:22]=1)=[O:47])([CH3:52])([CH3:51])[CH3:50]

Komponenten

6

Edukt 5

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 12446821Olopatadine Impurity 17

Produkt 1

HCID 196930162-Tert-butoxycarbonylamino-6,11-dihydrodibenz[b,e]oxepin-11-oneAusbeute 41 %

Versuchsvorschrift

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%).

Aufarbeitung

  1. temperatureby heating
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter the reaction mixture was cooled
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter the drying agent was filtered off
  8. concentrationthe organic layer was concentrated under reduced pressure
  9. customThe obtained oily substance was purified by silica gel column chromatography (hexane/ethyl acetate=8/1)

Quellen und Nachweise

ORD-Eintrag
ord-e2a46196bcf14ceb891b2c6cabfdc4c1
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726325

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