N,N'-Dimethylethylenediamine → 7-((R)-5-hydroxymethyl-2-oxooxazolidin-3-yl)-3-(2-methanesulfonylphenyl)-2H-isoquinolin-1-one

HRID 1162920Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1162920
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[S:19]([CH3:22])(=[O:21])=[O:20])[NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[OH:23][CH2:24][C@@H:25]1[O:29][C:28](=[O:30])[NH:27][CH2:26]1.C(=O)([O-])[O-].[K+].[K+].CNCCNC.[Cl-].[NH4+]>O1CCOCC1.[Cu](I)I>[OH:23][CH2:24][C@@H:25]1[O:29][C:28](=[O:30])[N:27]([C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[C:7]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[S:19]([CH3:22])(=[O:21])=[O:20])[NH:8][C:9]3=[O:12])=[CH:4][CH:3]=2)[CH2:26]1

Komponenten

8

Edukt 5

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 10236003(5R)-5-(hydroxymethyl)-1,3-oxazolidin-2-oneHCID 575579337-bromo-3-(2-methylsulfonylphenyl)-2H-isoquinolin-1-one

Produkt 1

HCID 118570957-((R)-5-hydroxymethyl-2-oxooxazolidin-3-yl)-3-(2-methanesulfonylphenyl)-2H-isoquinolin-1-oneAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

The 7-bromo-3-(2-methylsulfonylphenyl)-2H-isoquinolin-1-one (7 mg, 0.019 mmol) prepared in step A, copper iodide (I) (3.5 mg, 0.019 mmol), (R)-5-hydroxymethyloxazolidin-2-one (2.2 mg, 0.019 mmol), and potassium carbonate (5.3 mg, 0.039 mmol) were suspended in 1,4-dioxane (0.5 ml). Thereafter, N,N′-dimethylethylenediamine (0.01 ml, 0.093 mmol) was added to the suspension. The obtained mixture was stirred under heating to reflux overnight. The reaction solution was cooled to a room temperature. A saturated ammonium chloride aqueous solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=100:1->30:1), so as to obtain 7-((R)-5-hydroxymethyl-2-oxooxazolidin-3-yl)-3-(2-methanesulfonylphenyl)-2H-isoquinolin-1-one (2 mg, 26%) in the form of a colorless oil substance.

Aufarbeitung

  1. temperatureunder heating
  2. temperatureto reflux overnight
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=100:1->30:1)

Quellen und Nachweise

ORD-Eintrag
ord-ed064adada71424c85010f9a71e2f137
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820693B2

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