N,N'-Dimethylethylenediamine → (R)-3-{4-[4-(2,4-dimethylphenyl)piperazine-1-carbonyl]-3-methanesulfonylphenyl}-4-hydroxymethyloxazolidin-2-one

HRID 1804159Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1804159
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=3[CH3:23])[CH2:12][CH2:11]2)=[O:9])=[C:4]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:3]=1.[O:28]=[C:29]1[NH:33][C@H:32]([CH2:34][O:35]C(=O)C2C=CC=CC=2)[CH2:31][O:30]1.C(=O)([O-])[O-].[K+].[K+].CNCCNC>[Cu]I.O.C1(C)C=CC=CC=1>[CH3:23][C:17]1[CH:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:16]=1[N:13]1[CH2:14][CH2:15][N:10]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:33]3[C@H:32]([CH2:34][OH:35])[CH2:31][O:30][C:29]3=[O:28])=[CH:3][C:4]=2[S:24]([CH3:27])(=[O:26])=[O:25])=[O:9])[CH2:11][CH2:12]1

Komponenten

8

Edukt 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 16213752(4S)-4-(Benzoyloxymethyl)oxazolidine-2-oneHCID 58484856(4-Bromo-2-methanesulfonylphenyl)[4-(2,4-dimethylphenyl)piperazin-1-yl]methanone

Produkt 1

HCID 46190000(R)-3-{4-[4-(2,4-dimethylphenyl)piperazine-1-carbonyl]-3-methanesulfonylphenyl}-4-hydroxymethyloxazolidin-2-oneAusbeute 35,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a mixture of (4-bromo-2-methanesulfonylphenyl)[4-(2,4-dimethylphenyl)piperazin-1-yl]methanone (903 mg) described in Preparation Example 9, benzoic acid (R)-2-oxooxazolidin-4-ylmethyl ester (442 mg), potassium carbonate (553 mg) and copper (I) iodide (76 mg) were added toluene (4 mL) and N,N′-dimethylethylenediamine (100 μL), and the mixture was refluxed for 8 hr. After cooling, water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. The residue was purified by column chromatography (chloroform:methanol). To a solution of the obtained compound in dioxane (2 mL) and methanol (2 mL) was added 1 M aqueous sodium hydroxide solution (2 mL), and the mixture was stirred at room temperature for 3 hr. The mixture was extracted with chloroform, washed with saturated brine, and the solvent was evaporated. The residue was purified by column chromatography (chloroform:methanol) to give the title compound (344 mg).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 8 hr
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. customthe solvent was evaporated
  6. customThe residue was purified by column chromatography (chloroform:methanol)
  7. additionTo a solution of the obtained compound in dioxane (2 mL) and methanol (2 mL) was added 1 M aqueous sodium hydroxide solution (2 mL)
  8. extractionThe mixture was extracted with chloroform
  9. washwashed with saturated brine
  10. customthe solvent was evaporated
  11. customThe residue was purified by column chromatography (chloroform:methanol)

Quellen und Nachweise

ORD-Eintrag
ord-56f359c26ac24bfe8e68595227335223
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354401B2

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