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Water → 2-oxo-3-tert-butoxycarbonylamino-5-(2-thenoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

HRID 1979433
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Reaktionsgleichung

Reaktionsgleichung von HRID 1979433
[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].[S:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[C:27](Cl)=[O:28].N1C=CC=CC=1.O>ClCCCl>[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]([C:27](=[O:28])[C:23]2[S:22][CH:26]=[CH:25][CH:24]=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

6

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 789282-Thiophenecarbonyl chlorideHCID 212015812-oxo-3-tert-butoxycarbonylamino-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Produkt 1

HCID 212015632-oxo-3-tert-butoxycarbonylamino-5-(2-thenoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepineAusbeute 47,2 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

2-oxo-3-tert-butoxycarbonylamino-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (2.0 g) obtained from Referential Example 7 was suspended in 1,2-dichloroethane (20 ml), 2-thiophencarbonyl chloride (1.11 g) and pyridine (0.60 g) were added to the suspension, and the mixture was refluxed for 3 hours. The reaction mixture was allowed to cool, water was added to the mixture, extracted with chloroform. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography(n-hexane:ethyl acetate=2:1), to thereby obtain 1.30 g of the title compound as a light yellow crystal.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 3 hours
  2. temperatureto cool
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography(n-hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-332415e14aca446288fcaf3598a207a2
Quelldatensatz
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06239131B1

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