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

HRID 1664558Notes

Reaction equation

HRID 1664558 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 dissolved 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 C13H15N2O3 (M+H): 247.1. found 247.0.

Workup

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

Sources & evidence

ORD record
ord-1a2f8f95a1ad405da38430eac58b8956
Source dataset
uspto-grants-2011_10
Patent number
US08039478B2

Reaction notes

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