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

HRID 1451234
Notes
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Reaction equation

HRID 1451234 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-f706fd8fb0fd4a548d5d4ce54c768bed
Source dataset
uspto-grants-1997_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05604221

Reaction notes

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