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3-Bromocyclohexene → 2-oxo-3-tert-butoxycarbonylamino-5-(2-cyclohexene-1-yl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

HRID 1979345
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1979345
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:6]=2[NH:5][CH2:4][CH:3]1[NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].Br[CH:23]1[CH2:28][CH2:27][CH2:26][CH:25]=[CH:24]1.C(=O)(O)[O-].[Na+]>CO>[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:6]=2[N:5]([CH:28]2[CH2:27][CH2:26][CH2:25][CH:24]=[CH:23]2)[CH2:4][CH:3]1[NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]
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Komponenten

5

Edukt 3

HCID 1370573-BromocyclohexeneHCID 516892Sodium BicarbonateHCID 212015812-oxo-3-tert-butoxycarbonylamino-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Produkt 1

HCID 212015412-oxo-3-tert-butoxycarbonylamino-5-(2-cyclohexene-1-yl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepineAusbeute 35,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887
Methanol
Lösungsmittel

Versuchsvorschrift

2-Oxo-3-tert-butoxycarbonylamino-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (3.00 g) obtained from Referential Example 7 was suspended in methanol (30 ml), 90% 3-bromocyclohexene (6.08 g) and sodium bicarbonate (2.85 g) were added, and the mixture was stirred for 5 hours at room temperature. The reaction mixture was concentrated under reduced pressure, water (100 ml) was added to the residue, extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1), to thereby obtain 1.36 g of the titled compound.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure, water (100 ml)
  2. additionwas added to the residue
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-d14a4ec671804bc38c5154b01bb4ca8e
Quelldatensatz
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06239131B1

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