1,1'-Carbonyldiimidazole → Methyl 3-(3-benzyl-1,2,4-oxadiazol-5-yl)propanoate

HRID 1787798Notes

Reaction equation

HRID 1787798 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][CH2:3][C:4]([O-])=[O:5].C1N=CN(C(N2C=NC=C2)=O)C=1.O/[N:23]=[C:24](\[NH2:32])/[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C>[CH2:25]([C:24]1[N:32]=[C:4]([CH2:3][CH2:2][C:1]([O:8][CH3:9])=[O:7])[O:5][N:23]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 6930703Mono-Methyl SuccinateHCID 95664652-Phenylacetamidoxime

Product 1

HCID 59853830Methyl 3-(3-benzyl-1,2,4-oxadiazol-5-yl)propanoateYield 69.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Butanedioic acid, monomethyl ester (4.0 g, 30.3 mmole) and CDI (5.40 g, 33.3 mmole) were dissolved in anhydrous DMF (15 ml). After stirring the solution at room temperature for 3 hours, (1Z)-N′-hydroxy-2-phenylethanimidamide (5.0 g, 33.3 mmole) was added and the solution heated at 90° C. for 20 hours. After evaporation of solvent, the residue was dissovled in EtOAc. The organic phase was washed with water and brine, dried over Na2SO4. After filtration and evaporation of solvent, the residue was purified by flash chromatography on silica gel eluted with EtOAc/Hexane (25/75). The purification gave 5.2 g (69.7%) of product as light yellowish oil. LCMS calculated for C13H11N2O3(M+H): 247.1; found 247.0.

Workup

  1. temperaturethe solution heated at 90° C. for 20 hours
  2. customAfter evaporation of solvent
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration and evaporation of solvent
  6. customthe residue was purified by flash chromatography on silica gel
  7. washeluted with EtOAc/Hexane (25/75)
  8. customThe purification

Sources & evidence

ORD record
ord-589a443feaaf49d99d07b72436c20dee
Source dataset
uspto-grants-2009_03
Patent number
US07511050B2

Reaction notes

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