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

HRID 344023Notes

Reaction equation

HRID 344023 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-3b929a3e9de94848ba8b11a8b35983a3
Source dataset
uspto-grants-1999_01
Patent number
US05864045

Reaction notes

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