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

HRID 245414Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 245414
[Si:1]([O:18][CH2:19][C:20]1[C:21]([N:35]2[CH2:40][C@H:39]([CH3:41])[O:38][C@H:37]([CH3:42])[CH2:36]2)=[C:22]([F:34])[C:23]([F:33])=[C:24]([C:26](=[O:32])[C:27]([O:29]CC)=[O:28])[CH:25]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].C(O)(=O)C>C(O)C.O>[Si:1]([O:18][CH2:19][C:20]1[C:21]([N:35]2[CH2:36][C@H:37]([CH3:42])[O:38][C@H:39]([CH3:41])[CH2:40]2)=[C:22]([F:34])[C:23]([F:33])=[C:24]([C:26](=[O:32])[C:27]([OH:29])=[O:28])[CH:25]=1)([C:14]([CH3:16])([CH3:15])[CH3:17])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 14797Potassium Hydroxide3×HCID 86658065Ethyl 2-(5-((tert-butyldiphenylsilyloxy)methyl)-4-((2R,6S)-2,6-dimethylmorpholino)-2,3-difluorophenyl)-2-oxoacetate2×

Produkt 1

HCID 866580682-(5-((tert-butyldiphenylsilyloxy)methyl)-4-((2R,6S)-2,6-dimethylmorpholino)-2,3-difluorophenyl)-2-oxoacetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. stirringthe reaction was stirred at room temperature for 60 minutes
  2. extractionextracted three times with ethyl acetate
  3. washThe organic layers were washed twice with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. dissolutionThe resulting sticky oil was dissolved in ethyl acetate
  7. washwashed with sat. NaHCO3
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated
  10. customThe resulting oil was dried under vacuum for 2 hours

Quellen und Nachweise

ORD-Eintrag
ord-e901284158e84a7b96d4542364ff0b18
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658641B2

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