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Ammonium cerium (IV) nitrate → (3aR*,10aS*)-4-(phthalimidoacetyl)-9-(3,5,6-trimethyl-1,4-benzoquinon-2-ylmethyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

HRID 356161
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 356161
C[O:2][C:3]1[C:38]([CH3:39])=[C:37]([CH3:40])[C:36]([O:41]C)=[C:35]([CH3:43])[C:4]=1[CH2:5][N:6]1[C:12](=[O:13])[C@H:11]2[CH2:14][CH2:15][CH2:16][C@H:10]2[N:9]([C:17](=[O:30])[CH2:18][N:19]2[C:23](=[O:24])[C:22]3=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]3[C:20]2=[O:29])[C:8]2[CH:31]=[CH:32][CH:33]=[CH:34][C:7]1=2.[N+]([O-])([O-])=O.[Ce+4].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O>C(#N)C.O>[C:20]1(=[O:29])[N:19]([CH2:18][C:17]([N:9]2[C@@H:10]3[CH2:16][CH2:15][CH2:14][C@@H:11]3[C:12](=[O:13])[N:6]([CH2:5][C:4]3[C:3](=[O:2])[C:38]([CH3:39])=[C:37]([CH3:40])[C:36](=[O:41])[C:35]=3[CH3:43])[C:7]3[CH:34]=[CH:33][CH:32]=[CH:31][C:8]2=3)=[O:30])[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]12
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 9869224Ammonium cerium (IV) nitrateHCID 86753321(3aR*,10aS*)-9-(2,5-dimethoxy-3,4,6-trimethylbenzyl)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

Produkt 1

HCID 70111246(3aR*,10aS*)-4-(phthalimidoacetyl)-9-(3,5,6-trimethyl-1,4-benzoquinon-2-ylmethyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-oneAusbeute 63,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
3×
HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

In a mixture of acetonitrile (3 mL) and water (2 mL) was suspended (3aR*,10aS*)-9-(2,5-dimethoxy-3,4,6-trimethylbenzyl)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (0.5 g, 0.86 mmol). To the suspension was added, while stirring, a solution of ammonium cerium (IV) nitrate (1.4 g, 2.55 mmol) in a mixture of acetonitrile (2 mL) and water (2 mL). The reaction mixture was stirred for one hour, which was diluted with water, followed by extraction with chloroform. The extract was washed with water and dried, then the solvent was distilled off. The residue was crystallized from ethyl acetate to give 300 mg (yield 63%) of the titled compound, m.p. 258°-260° C.

Aufarbeitung

  1. additionTo the suspension was added
  2. stirringThe reaction mixture was stirred for one hour
  3. extractionfollowed by extraction with chloroform
  4. washThe extract was washed with water
  5. customdried
  6. distillationthe solvent was distilled off
  7. customThe residue was crystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-847abb0f88834618ac59ca324403a869
Quelldatensatz
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05834463

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