Oxygen → HCID 23225813, compound

HRID 344025Notes

Reaction equation

HRID 344025 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:12][CH:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[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].ClCCl.[O:29]=O.CSC>C(OCC)(=O)C.CO>[C:1]([O:5][C:6]([N:8]([CH2:12][CH:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:9][CH:10]=[O:29])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 977OxygenHCID 1068Dimethyl SulfideHCID 6344DichloromethaneHCID 54079479HCID 54079479, compound

Product 1

HCID 23225813HCID 23225813, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

Combine N-t-butoxycarbonyl-N-allyl-2,2-bis-phenyl-ethylamine (0.23 g, 0.68 mmol) and dichloromethane (10 mL) and methanol (0.5 mL). Cool the -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 (2.0 mL). Allow the reaction mixture to warm to ambient temperature and stir for 5.5 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-6daec64481d6447ba6c002f191517433
Source dataset
uspto-grants-1999_01
Patent number
US05864045

Reaction notes

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