Methanol → (Z)-2-(furan-2-carbonylamino)-3-(5-phenyl-2-furyl)prop-2-enoic Acid

HRID 1823955

Reaktionsgleichung

[OH-:1].[Na+].O.[O:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]1[O:10][C:11](=[O:26])/[C:12](=[CH:14]/[C:15]2[O:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:18][CH:19]=2)/[N:13]=1.CO>CC(C)=O>[O:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]([NH:13]/[C:12](=[CH:14]\[C:15]1[O:16][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:18][CH:19]=1)/[C:11]([OH:10])=[O:26])=[O:1]

Komponenten

Reaktionsbedingungen

Temperatur: 75 °C

Versuchsvorschrift

1N NaOH (100 μL) and H2O (500 μL) is added to a solution of (4Z)-2-(2-furyl)-4-[(5-phenyl-2-furyl)methylene]-1,3-oxazol-5(4H)-one (10 mg, 0.0327 mmol), prepared as described above, in acetone (1 mL). The reaction mixture is heated to 75° C. for one hour and then cooled to 25° C. The crude mixture is loaded onto a QAX column, which was pre-treated with MeOH. After 2 minutes the column is washed with MeOH and the product is eluted with 3% HCl/MeOH. Subsequently, the column is washed with MeOH (2 mL) and the combined washings are concentrated under reduced pressure to provide 9.5 mg of (2Z)-2-(2-furoylamino)-3-(5-phenyl-2-furyl)prop-2-enoic acid.

Aufarbeitung

customprepared
temperaturecooled to 25° C
washAfter 2 minutes the column is washed with MeOH
washthe product is eluted with 3% HCl/MeOH
washSubsequently, the column is washed with MeOH (2 mL)
concentrationthe combined washings are concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-10ca92942e8147eb8665ae8b5bdcf3f2
Quelldatensatz: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07041690B2

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