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

HRID 600594
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 600594
[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
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

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 70 %

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 dissolved in anhydrous DMF (15 ml) and stirred at room temperature for 3 hours. (1Z)-N′-hydroxy-2-phenylethanimidamide (5.0 g, 33.3 mmole) was added to above solution and the mixture was stirred at 90° C. for 20 hours. The reaction mixture was concentrated and the residue was diluted with water and EtOAc. The organic layer was washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (elution with 1:3 ethyl acetate:hexane) to give the desired product as light yellowish oil (5.2 g, 70% yield). LCMS calculated for C13H15N2O3 (M+H): 247.1. found: 247.1.

Aufarbeitung

  1. stirringthe mixture was stirred at 90° C. for 20 hours
  2. concentrationThe reaction mixture was concentrated
  3. additionthe residue was diluted with water and EtOAc
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (elution with 1:3 ethyl acetate:hexane)

Quellen und Nachweise

ORD-Eintrag
ord-c0a52cddec654979afd75933b45ab782
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07902205B2

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