Sodium hydride → N-(5R)-[3-(3-Fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl]N-isoxazol-3-yl-carbamic acid tert-butyl ester

HRID 747215

Reaktionsgleichung

Reaktionsgleichung von HRID 747215
[H-].[Na+].[C:3]([O:7][C:8](=[O:15])[NH:9][C:10]1[CH:14]=[CH:13][O:12][N:11]=1)([CH3:6])([CH3:5])[CH3:4].[F:16][C:17]1[CH:18]=[C:19]([N:24]2[CH2:28][C@H:27]([CH2:29]OS(C)(=O)=O)[O:26][C:25]2=[O:35])[CH:20]=[CH:21][C:22]=1[I:23]>CN(C)C=O.C(=O)(O)[O-].[Na+]>[C:3]([O:7][C:8](=[O:15])[N:9]([CH2:29][C@@H:27]1[O:26][C:25](=[O:35])[N:24]([C:19]2[CH:20]=[CH:21][C:22]([I:23])=[C:17]([F:16])[CH:18]=2)[CH2:28]1)[C:10]1[CH:14]=[CH:13][O:12][N:11]=1)([CH3:6])([CH3:4])[CH3:5]

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 21992950tert-Butyl 1,2-oxazol-3-ylcarbamateHCID 23624705Methanesulfonic acid (5R)-3-(3-fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl ester

Produkt 1

HCID 59749411N-(5R)-[3-(3-Fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl]N-isoxazol-3-yl-carbamic acid tert-butyl esterAusbeute 57,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel3×HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To sodium hydride (60% in oil, 9.04 mM) suspended in dry N,N-dimethylformamide (10 ml) under nitrogen, N-isoxazol-3-yl-carbamic acid tert-butyl ester (1.66 g, 9.04 mM) in N,N-dimethylformamide (10 ml) was added dropwise at ambient temperature. Methanesulfonic acid (5R)-3-(3-fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl ester (2.5 g, 6.02 mM) in N,N-dimethylformamide (10 ml) was added slowly, and the mixture heated to 75° for 2 hours. After cooling, the mixture was diluted with aqueous sodium bicarbonate (5%, 300 ml), and extracted with ethyl acetate (3×100 ml). The organic phase was washed with water (100 ml) and brine (100 ml), dried (magnesium sulfate), evaporated and crude product purified by chromatography on a 50 g silica Mega Bond Elut® column, eluting with dichloromethane. Relevant fractions were combined to give the title compound (1.73 g).

Aufarbeitung

  1. temperaturethe mixture heated to 75° for 2 hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate (3×100 ml)
  4. washThe organic phase was washed with water (100 ml) and brine (100 ml)
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated
  7. customcrude product purified by chromatography on a 50 g silica Mega Bond Elut® column
  8. washeluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-03a142c522a44f3d8773e3dbe0f4459b
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07396847B2

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