Oxygen → N-t-butoxycarbonyl-N-(2-oxo-ethyl)-2-phenyl-ethylamine

HRID 356861Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 356861
[C:1]([O:5][C:6]([N:8]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:9][CH:10]=C)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:20]=O.CSC>ClCCl.CO.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:9][CH:10]=[O:20])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 3

HCID 977OxygenHCID 1068Dimethyl SulfideHCID 53637355N-allyl-N-phenethylcarbamic acid tert-butyl ester

Produkt 1

HCID 23225807N-t-butoxycarbonyl-N-(2-oxo-ethyl)-2-phenyl-ethylamine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Dissolve N-t-butoxycarbonyl-N-allyl-2-phenyl-ethylamine (7.88 g, 21.44 mmol) in dichloromethane (200 mL) and methanol (5 mL). Cool to -78° C. Pass ozonized oxygen through the solution until a persistent light blue color is obtained. Pass nitrogen through the solution until the blue color dissipates. Add dimethyl sulfide (20 mL). Allow the reaction mixture to warm to ambient temperature and stir for 5 hours. Concentrate in vacuo to obtain a residue. Dilute the residue with ethyl acetate and extract with water. Separate the layers, dry the organic layer over MgSO4, filter, and evaporate in vacuo to give the title compound.

Aufarbeitung

  1. customis obtained
  2. temperatureto warm to ambient temperature
  3. concentrationConcentrate in vacuo
  4. customto obtain a residue
  5. extractionextract with water
  6. customSeparate the layers
  7. dry with materialdry the organic layer over MgSO4
  8. filtrationfilter
  9. customevaporate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-001047ccd7914986a2b6c586054ecd09
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05840726

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