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

HRID 356861Notes

Reaction equation

HRID 356861 reaction equation
[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]

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-001047ccd7914986a2b6c586054ecd09
Source dataset
uspto-grants-1998_11
Patent number
US05840726

Reaction notes

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