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Ozone → 2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl-5-oxo-pentylamine

HRID 2395969
Notes
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Reaction equation

HRID 2395969 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]([CH2:25][CH2:26][CH:27]=C)[C:13]([NH:15][CH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:14].[O:29]=[O+][O-]>C(Cl)Cl.CO>[O:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[N:3]1[CH:12]([CH2:25][CH2:26][CH:27]=[O:29])[C:13]([NH:15][CH2:16][CH2:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:14]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 24823OzoneHCID 540472832-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl-5-hexenylamine

Product 1

HCID 867471452-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl-5-oxo-pentylamineYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344Dichloromethane
Solvent

Conditions

Temperature
-78 °C

Procedure

Dissolve 2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl-5-hexenylamine (1.2 g, 3.19 mmol) in methylene chloride (40 mL) and methanol (4 mL) and cool to -78° C. under a nitrogen atmosphere. Treat with ozone until a blue color persists, degas with nitrogen for 20 minutes and add pyridine (0.2 mL). Quench with dimethylsulfide (4 mL) and stir overnight at room temperature. Dilute with methylene chloride (75 mL) and wash with 5% sulfuric acid (40 mL) and brine (40 mL). Dry (Na2SO4), evaporate the solvent in vacuo and purify by chromatography (hexane/ethyl acetate) to give 2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl-5-oxo-pentylamine as a white solid (972 mg, 80%).

Workup

  1. customdegas with nitrogen for 20 minutes
  2. additionadd pyridine (0.2 mL)
  3. customQuench with dimethylsulfide (4 mL)
  4. additionDilute with methylene chloride (75 mL)
  5. washwash with 5% sulfuric acid (40 mL) and brine (40 mL)
  6. dry with materialDry (Na2SO4)
  7. customevaporate the solvent in vacuo
  8. custompurify by chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9ad1f3eb7fb6498a93ed7d812f7f13f1
Source dataset
uspto-grants-1996_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05491142

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes