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Oxygen → (S)-N-benzyl-N-methyl-2-[N-(t-butoxycarbonyl)-2-oxo-ethylamino]-3-phenyl-propionamide

HRID 1379960
Notes
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Reaction equation

HRID 1379960 reaction equation
[CH2:1]([N:8]([CH3:30])[C:9](=[O:29])[C@@H:10]([N:18]([CH2:26][CH:27]=C)[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[O:37]=O.CSC>ClCCl.CO.C(OCC)(=O)C>[CH2:1]([N:8]([CH3:30])[C:9](=[O:29])[C@@H:10]([N:18]([CH2:26][CH:27]=[O:37])[C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 977OxygenHCID 1049PyridineHCID 1068Dimethyl SulfideHCID 54096526(S)-N-Benzyl-N-methyl-2-[N-(t-butoxycarbonyl)-allylamino]-3-phenyl-propionamide

Product 1

HCID 53842533(S)-N-benzyl-N-methyl-2-[N-(t-butoxycarbonyl)-2-oxo-ethylamino]-3-phenyl-propionamide

Reagents, catalysts & solvents 2

HCID 8857
Ethyl Acetate
Solvent
HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
-78 °C

Procedure

Combine (S)-N-benzyl-N-methyl-2-[N'-(t-butoxycarbonyl)-allylamino]-3-phenyl-propionamide (10.04 g, 24.5 mmol), and pyridine (0.13 ml) in dichloromethane/methanol (300 mL/30 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 (55 mL). Allow the reaction mixture to warm to ambient temperature and stir for 16 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. Chromatograph on silica gel eluting with 10% ethyl acetate/hexane to give the title compound: TLC Rf =0.53 (silica gel, 10% ethyl acetate/hexane).

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-270ec43201344f038523f49e1d8b2e67
Source dataset
uspto-grants-1997_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05672602

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes