Triethylamine → 3-[(Z)-N-[(2-amino-1,3-thiazol-4-yl)methoxy]-C-phenylcarbonimidoyl]-2-methyl-1,2,4-oxadiazol-5-one

HRID 520247

Reaktionsgleichung

[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8]/[N:9]=[C:10](/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)\[C:11](=[NH:15])[N:12]([OH:14])[CH3:13])[N:6]=1.C(N(CC)CC)C.Cl[C:30](OC1C=CC(F)=CC=1)=[O:31]>CN(C=O)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8]/[N:9]=[C:10](/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)\[C:11]2[N:12]([CH3:13])[O:14][C:30](=[O:31])[N:15]=2)[N:6]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of (2Z)-2-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}-N-hydroxy-N-methyl-2-phenylethanimidamide (5.00 g, 16.37 mmol, 1 eq.) and triethylamine (2.28 ml, 16.37 mmol, 1 eq) in DMF (100 ml) at 0° C., was added dropwise 4-fluorophenyl chloroformate (28.58 g, 16.37 mmol, 1 eq.). After stirring at 0° C. for 1 hour, the reaction was quenched by addition of water (50 ml) and extracted with EtOAc (2×150 ml). The organics were combined, dried over MgSO4 and concentrated. The residue was purified by chromatography on silica gel to give 3-[(Z)-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}(phenyl)methyl]-2-methyl-1,2,4-oxadiazol-5(2H)-one (5.65 g, 96% yield).

Aufarbeitung

customthe reaction was quenched by addition of water (50 ml)
extractionextracted with EtOAc (2×150 ml)
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag: ord-066e9ff338f24b359bec8ecd27eb832c
Quelldatensatz: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09326515B2

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