Water → HCID 58840977, Verbindung

HRID 1268987

Reaktionsgleichung

Reaktionsgleichung von HRID 1268987
[N-:1]=[N+:2]=[N-:3].[Na+].CS(O[CH2:10][C@@H:11]1[O:15][C:14](=[O:16])[N:13]([C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24]3)=[C:19]([F:29])[CH:18]=2)[CH2:12]1)(=O)=O.C(OCC)(=O)C.O>CN(C=O)C.C1OCCOCCOCCOCCOCCOC1>[N:1]([CH2:10][C@@H:11]1[O:15][C:14](=[O:16])[N:13]([C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24]3)=[C:19]([F:29])[CH:18]=2)[CH2:12]1)=[N+:2]=[N-:3]

Komponenten

7

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 21356562(5R)-3-[3-fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-ylmethyl methanesulfonate

Produkt 1

HCID 58840977HCID 58840977, VerbindungAusbeute 71,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2855718-Crown-6KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Sodium azide (0.596 g, 9.08 mmol) and 18-crown-6 (0.025 g, 0.095 mmol) were added to a solution of (5R)-3-[3-fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-ylmethyl methanesulfonate (WO 01/81350) (3.161 g, 8.56 mmol) in DMF (8.5 ml). The reaction mixture was heated to 90° C. under an atmosphere of nitrogen for 19 h. It was poured into a mixture of ethyl acetate and water and was extracted three times with ethyl acetate. The combined organic layers were washed once with brine, dried over sodium sulfate, filtered and the solvent was removed under vacuum to give 1.94 g of product as a white solid.

Aufarbeitung

  1. extractionwas extracted three times with ethyl acetate
  2. washThe combined organic layers were washed once with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-7b032021c5a948699dc670edcba416a4
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199143B2

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