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Tetrahydrofuran → (4S,5S)-4-methyl5-Phenyl-3-(2-methoxyphenylacetyl)-2-oxazolidinone

HRID 1599132
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1599132
[H-].[Na+].[C:3](Cl)(=[O:8])C(C)(C)C.[CH2:10]([Li])[CH2:11][CH2:12][CH3:13].[CH3:15][C@H:16]1[C@H:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:19][C:18](=[O:27])[NH:17]1.[Cl-].[NH4+].[O:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1>CCCCCC.C(OCC)(=O)C>[CH3:15][C@H:16]1[C@H:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:19][C:18](=[O:27])[N:17]1[C:34](=[O:30])[CH2:33][C:32]1[CH:13]=[CH:12][CH:11]=[CH:10][C:31]=1[O:8][CH3:3]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 6

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 62493Pivaloyl chlorideHCID 11095183(4S,5S)-4-Methyl-5-phenyl-2-oxazolidinoneHCID 178418339Butyllithium

Produkt 1

HCID 57297643
(4S,5S)-4-methyl5-Phenyl-3-(2-methoxyphenylacetyl)-2-oxazolidinone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

9.38 g of 2-methoryphenylacetic acid are added at room temperature to a suspension of 1.89 [lacuna] of sodium hydride (80% dispersion in petroleum jelly) in 200 cm3 of dry tetrahydrofuran. This suspension is cooled to -30° C., 7.77 cm3 of pivaloyl chloride are added, and then finally a solution, cooled to -78° C., is added which is obtained by adding a solution of 35.27 cm3 of 1.6M butyllithium in hexane to a solution, cooled to -78° C., of 10 g of (4S,5S)-4-methyl-5-phenyl-oxazolidin-2-one in 200 cm3 of dry tetrahydrofuran. The reaction mixture is stirred at -30° C. for 45 minutes and then, after returning to room temperature, 200 cm3 of saturated aqueous ammonium chloride solution are added followed by 500 cm3 of ethyl acetate; after separation of the phases by decanting, the organic phase is washed twice with 100 cm3 of water and then twice with 100 cm3 of saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column (particle size 0.04-0.06 mm, diameter 4.8 cm, height 36 cm), eluting under a pressure of 0.6 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (85:15 then 80:20 by volume) and collecting fractions of 50 cm3. Fractions 14 to 31 are combined and concentrated to dryness under reduced pressure (2.7 kPa). 13.6 g of (4S,5S)-4-methyl-5-phenyl-3-(2-methoxyphenylacetyl)oxazolidin-2-one are obtained in the form of a yellow oil.

Aufarbeitung

  1. temperaturefinally a solution, cooled to -78° C.
  2. additionis added which
  3. customis obtained
  4. customafter returning to room temperature
  5. customafter separation of the phases
  6. customby decanting
  7. washthe organic phase is washed twice with 100 cm3 of water
  8. dry with materialtwice with 100 cm3 of saturated aqueous sodium chloride solution, dried over magnesium sulphate
  9. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  10. customThe residue is chromatographed on a silica gel column (particle size 0.04-0.06 mm, diameter 4.8 cm, height 36 cm)
  11. washeluting under a pressure of 0.6 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (85:15
  12. custom80:20 by volume) and collecting fractions of 50 cm3
  13. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Quellen und Nachweise

ORD-Eintrag
ord-32a885dadf8f414ea9be8c30d315cb21
Quelldatensatz
uspto-grants-1998_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05739351

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