Sodium Bicarbonate → (5R)-3-(3-Fluoro-4-(2-methylimidazol-1-yl)phenyl)-5-hydroxymethyloxazolidin-2-one

HRID 723772

Reaktionsgleichung

Reaktionsgleichung von HRID 723772
C(O[C:9]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([N:19]2[CH:23]=[CH:22][N:21]=[C:20]2[CH3:24])=[C:16]([F:18])[CH:17]=1)=O)C1C=CC=CC=1.C([Li])CCC.[CH2:30]([O:34][C:35](=[O:39])CCC)[C@@H:31]1[O:33]C1.C(=O)(O)[O-].[Na+]>O1CCCC1.CN1CCCN(C)C1=O.C(OCC)(=O)C>[F:18][C:16]1[CH:17]=[C:12]([N:11]2[CH2:9][C@H:30]([CH2:31][OH:33])[O:34][C:35]2=[O:39])[CH:13]=[CH:14][C:15]=1[N:19]1[CH:23]=[CH:22][N:21]=[C:20]1[CH3:24]

Komponenten

8

Edukt 4

HCID 516892Sodium BicarbonateHCID 2724536(2R)-Oxiran-2-ylmethyl butanoateHCID 218766515-Benzyloxycarbonylamino-2-(2-methyl-imidazol-1-yl)fluorobenzeneHCID 178418339Butyllithium

Produkt 1

HCID 21356557(5R)-3-(3-Fluoro-4-(2-methylimidazol-1-yl)phenyl)-5-hydroxymethyloxazolidin-2-oneAusbeute 44,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittelHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Lösungsmittel

Versuchsvorschrift

5-Benzyloxycarbonylamino-2-(2-methylimidazol-1-yl)fluorobenzene (54 g, 0.166 M) was dissolved in a mixture of dry tetrahydrofuran (600 ml) and 1,3-dimethyl-tetrahydropyrimidin-2-one (100 ml) under nitrogen, cooled to −70°, and treated with a solution of n-butyllithium (1.6M in isohexane, 114 ml), over 30 minutes. After stirring for 30 minutes at −70°, a solution of (R)-glycidylbutyrate (26.35 g, 0.183 M) in dry tetrahydrofuran (50 ml) was added over 15 minutes. Stirring was continued for 16 hours allowing the temperature to rise to ambient. The mixture was treated with aqueous sodium bicarbonate (5%, 500 ml) and ethyl acetate (800 ml), the organic layer separated, and the aqueous extracted with further ethyl acetate (3×750 ml). The combined extracts were dried (magnesium sulfate) and evaporated, and the resulting oil triturated with diethyl ether. The resulting solid was recrystallisd from isopropanol to give the title compound (21.5 g).

Aufarbeitung

  1. temperaturecooled to −70°
  2. stirringStirring
  3. waitwas continued for 16 hours
  4. customthe organic layer separated
  5. extractionthe aqueous extracted with further ethyl acetate (3×750 ml)
  6. dry with materialThe combined extracts were dried (magnesium sulfate)
  7. customevaporated
  8. customthe resulting oil triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-c1d982bee00542ee9f3a54dcce596308
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141583B2

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