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

HRID 2368597Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2368597
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 59853830Methyl 3-(3-benzyl-1,2,4-oxadiazol-5-yl)propanoateAusbeute 69,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Butanedioic acid, monomethyl ester (4.0 g, 30.3 mmole) and CDI (5.40 g, 33.3 mmole) were dissoled 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 dissoled 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 chromatogarphy 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.

Aufarbeitung

  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 chromatogarphy on silica gel
  7. washeluted with EtOAc/Hexane (25/75)
  8. customThe purification

Quellen und Nachweise

ORD-Eintrag
ord-dbea4dabd75e4501bd4c58f2a57a6d8c
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703783B2

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