Réaction #607429

Équation de réaction

(2Z)-2-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}-N-hydroxy-N-methyl-2-phenylethanimidamide

triethylamine

4-fluorophenyl chloroformate

→

3-[(Z)-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}(phenyl)methyl]-2-methyl-1,2,4-oxadiazol-5(2H)-one

Rendement 104.2%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Autrethe reaction was quenched by addition of water (50 ml)
2. 2
   Extractionextracted with EtOAc (2×150 ml)
3. 3
   Séchagedried over MgSO4
4. 4
   Concentrationconcentrated
5. 5
   AutreThe residue was purified by chromatography on silica gel

Mode opératoire

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).

Source