Reaktion #332633

Reaktionsgleichung

Ethyl 2-(5-((tert-butyldiphenylsilyloxy)methyl)-4-((2R,6S)-2,6-dimethylmorpholino)-2,3-difluorophenyl)-2-(hydroxyimino)acetate

Intermediate 165

Ethyl 2-(5-((tert-butyldiphenylsilyloxy)methyl)-4-((2R,6S)-2,6-dimethylmorpholino)-2,3-difluorophenyl)-2-(hydroxyimino)acetate

Sodium hydride

→

title compound

Ausbeute 66.6%

ethyl 5-((tert-butyldiphenylsilyloxy)methyl)-6-((2R,6S)-2,6-dimethylmorpholino)-7-fluorobenzo[d]isoxazole-3-carboxylate

Ausbeute 66.6%

Lösungsmittel

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled in an ice bath
2. 2
   workup.ADDITIONadded to the reaction flask
3. 3
   SonstigeThe ice bath was removed
4. 4
   SonstigeThe reaction was quenched with sat NH4Cl (5 ml)
5. 5
   workup.ADDITIONdiluted with water
6. 6
   Extraktionextracted three times with ethyl acetate
7. 7
   Waschenwashed with water and brine 5×
8. 8
   Trocknendried over MgSO4
9. 9
   Einengenconcentrated
10. 10
    SonstigeThe residue was purified by silica gel column chromatography

Vorschrift

Sodium hydride (0.159 g, 3.97 mmol) was suspended in 20 ml of DMF and cooled in an ice bath. Ethyl 2-(5-((tert-butyldiphenylsilyloxy)methyl)-4-((2R,6S)-2,6-dimethylmorpholino)-2,3-difluorophenyl)-2-(hydroxyimino)acetate (Intermediate 165, 1.94 g, 3.18 mmol) was dissolved in 20 ml of DMF and added to the reaction flask. The ice bath was removed and the reaction stirred at room temperature for 2 hours. The reaction was quenched with sat NH4Cl (5 ml), diluted with water and extracted three times with ethyl acetate. The organic layers were combined, washed with water and brine 5×, dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography using a gradient of hexanes to ethyl acetate to give the title compound (1.250 g, 66.6%).

Quelle