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Ethyl Acetate → (R)-(-)-2-oxo-3-tert-butoxycarbonylamino-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

HRID 352383
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 352383
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[NH:5][CH2:4][C@H:3]1[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].[CH:21]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]CC=1.C(OCC)(=O)C>C1(=O)CCCCC1.[C].[Pd]>[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:21]=2)[CH2:4][C@H:3]1[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]
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Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 136091-CycloocteneHCID 12988641(R)-2-oxo-3-tert-butoxycarbonylamino-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Produkt 1

HCID 12988647(R)-(-)-2-oxo-3-tert-butoxycarbonylamino-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepineAusbeute 50,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390
HCID 178418390, Verbindung
Katalysator
HCID 7967CyclohexanoneLösungsmittel

Reaktionsbedingungen

Temperatur
145 °C

Versuchsvorschrift

To a solution of 5 g of (R)-(+)-2-oxo-3-tert-butoxycarbonylamino-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine in 25 ml of cyclohexanone were added 5.96 g of cyclooctene and 0.5 g of 10% palladium carbon. The mixture was stirred at the internal temperature of 145° C. for 2.5 hours. After the reaction mixture was cooled to room temperature, 20 ml of ethyl acetate was added. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was crystallized by adding thereto diisopropyl ether and n-hexane and the resulting crystals were collected by filtration, whereby 3.2 g of the title compound was obtained.

Aufarbeitung

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was crystallized
  5. additionby adding
  6. filtrationdiisopropyl ether and n-hexane and the resulting crystals were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-cd97a41839564bccb51d26a6e8f7ae1f
Quelldatensatz
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06747022B2

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