Methyl morpholine oxide → Pnu-288034

HRID 395259

Reaktionsgleichung

Reaktionsgleichung von HRID 395259
[F:1][C:2]1[CH:3]=[C:4]([N:15]2[CH2:19][C@H:18]([CH2:20][NH:21][C:22](=[O:24])[CH3:23])[O:17][C:16]2=[O:25])[CH:5]=[C:6]([F:14])[C:7]=1[N:8]1[CH2:13][CH2:12][S:11][CH2:10][CH2:9]1.C[N+]1([O-])CC[O:30]CC1.[OH2:34].CC(C)=O>[Os](=O)(=O)(=O)=O>[O:34]=[S:11]1(=[O:30])[CH2:12][CH2:13][N:8]([C:7]2[C:2]([F:1])=[CH:3][C:4]([N:15]3[CH2:19][C@H:18]([CH2:20][NH:21][C:22](=[O:24])[CH3:23])[O:17][C:16]3=[O:25])=[CH:5][C:6]=2[F:14])[CH2:9][CH2:10]1

Komponenten

5

Edukt 3

HCID 82029Methyl morpholine oxide2×HCID 10109766N-({(5S)-3-[3,5-difluoro-4-(4-thiomorpholinyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamideHCID 18366337Propan-2-one--water (1/1)

Produkt 1

HCID 9931003Pnu-288034Ausbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 30318Osmium TetroxideKatalysator3×

Versuchsvorschrift

N-({(5S)-3-[3,5-difluoro-4-(4-thiomorpholinyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide (13.36 g, 35.97 mmol) is dissolved in a solution of 25% water/acetone and then treated sequentially with 4-Methylmorpholine N-oxide (3 eq, 12.64 g, 107.91 mmol) and a catalytic amount of osmium tetroxide (2.8 mL). The reaction is stirred overnight at room temperature under nitrogen. In the morning, another 2 mL of osmium tetroxide is added. Another 2 eq of 4-Methylmorpholine N-oxide and 2.5 mL of osmium tetroxide are added a few hours later. The reaction is stirred overnight again under nitrogen. The following morning, the reaction is complete. The reaction mixture is quenched with a solution of sodium hydrosulfite and then extracted with methylene chloride three times. The organic layer is washed with sodium hydrosulfite and brine, dried with sodium sulfate, filtered, and concentrated. The crude product is then chomatographed on silica gel, eluting with methylene chloride and then 2% and 5% methanol/methylene chloride solutions. Appropriate fractions are combined and concentrated to yield 11.99 g (83%) of the title compound as a white solid, mp: 187-189.5° C.

Aufarbeitung

  1. stirringThe reaction is stirred overnight again under nitrogen
  2. customThe reaction mixture is quenched with a solution of sodium hydrosulfite
  3. extractionextracted with methylene chloride three times
  4. washThe organic layer is washed with sodium hydrosulfite and brine
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washeluting with methylene chloride
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-eb7c889ddbf840c1bf7be46c3dbc5558
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06605609B2

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