Reaktion #332596

Reaktionsgleichung

KOH

acetic acid

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

Intermediate 114

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

KOH

KOH

→

title compound

2-(5-((tert-butyldiphenylsilyloxy)methyl)-4-((2R,6S)-2,6-dimethylmorpholino)-2,3-difluorophenyl)-2-oxoacetic acid

Lösungsmittel

water

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction was stirred at room temperature for 60 minutes
2. 2
   Extraktionextracted three times with ethyl acetate
3. 3
   WaschenThe organic layers were washed twice with brine
4. 4
   Trocknendried over MgSO4
5. 5
   Einengenconcentrated
6. 6
   workup.DISSOLUTIONThe resulting sticky oil was dissolved in ethyl acetate
7. 7
   Waschenwashed with sat. NaHCO3
8. 8
   Trocknendried over MgSO4
9. 9
   Einengenconcentrated
10. 10
    SonstigeThe resulting oil was dried under vacuum for 2 hours

Vorschrift

Ethyl 2-(5-((tert-butyldiphenylsilyloxy)methyl)-4-((2R,6S)-2,6-dimethylmorpholino)-2,3-difluorophenyl)-2-oxoacetate (Intermediate 114, 0.785 g, 3.00 mmol) was dissolved in ethanol (60 ml) and stirred at room temperature with 1 ml of 10% KOH. After 3 hours the reaction appears to have gone approximately 40-50% by LCMS. An additional 1 ml of 10% KOH was added and the reaction was stirred at room temperature for 30 minutes. The reaction has 70-80% by LCMS. An additional 1 ml of 10% KOH was added and the reaction was stirred at room temperature for 60 minutes. The reaction was made acidic with acetic acid, diluted with water and extracted three times with ethyl acetate. The organic layers were washed twice with brine, dried over MgSO4 and concentrated. The resulting sticky oil was dissolved in ethyl acetate, washed with sat. NaHCO3, dried over MgSO4 and concentrated. The resulting oil was dried under vacuum for 2 hours to give the title compound as a yellow solid.

Quelle