Sulfuric Acid → (S)-7-[(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)]-1,2,6,7,8,12b-hexahydro-6-oxopyrido[2,1-a][2]benzazepine

HRID 342898

Reaktionsgleichung

Reaktionsgleichung von HRID 342898
S(=O)(=O)(O)O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[O:19]=[C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](=[O:29])[N:21]1[C@@H:30]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:31]([N:33]1[CH:38]=[CH:37][CH2:36][CH:35]=[CH:34]1)=[O:32].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.CCCCCC>[O:29]=[C:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:20](=[O:19])[N:21]1[C@H:30]1[CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[CH:34]2[CH2:35][CH2:36][CH:37]=[CH:38][N:33]2[C:31]1=[O:32]

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 15380836(S)-N-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-1,4-dihydro-pyridine

Produkt 1

HCID 9863597(S)-7-[(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)]-1,2,6,7,8,12b-hexahydro-6-oxopyrido[2,1-a][2]benzazepine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226206Ethyl acetate hexaneLösungsmittel2×

Versuchsvorschrift

Combine sulfuric acid (3.0 mL, 96%) and trifluoroacetic anhydride (300 mL). Add (S)-N-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-1,4-dihydro-pyridine (1.0 mmol). After 30 minutes, pour the reaction mixture into mixture of saturated aqueous sodium bicarbonate and ice. Extract with ethyl acetate and then with methylene chloride. Combine the organic layers and filter through a plug of silica gel. Rinse the silica gel with dichloromethane. Evaporate the filtrate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with 10% ethyl acetate/hexane and then 25% ethyl acetate/hexane to give the title compound.

Aufarbeitung

  1. additionpour the reaction mixture
  2. extractionExtract with ethyl acetate
  3. filtrationfilter through a plug of silica gel
  4. washRinse the silica gel with dichloromethane
  5. customEvaporate the filtrate in vacuo
  6. customto give a residue

Quellen und Nachweise

ORD-Eintrag
ord-3c1672865aea43538351043f1ac29aa6
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05859252

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