Phosphorus oxychloride → HCID 131714060, Verbindung

HRID 569446

Reaktionsgleichung

Reaktionsgleichung von HRID 569446
C[N+](C)=CCl.[Cl-].P(Cl)(Cl)(Cl)=O.[Cl:12][CH2:13][C:14](=[O:26])[C:15](=[N:19][O:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[C:16]([OH:18])=O.[NH2:27][CH:28]1[C:40](=[O:41])[N:30]2[C:31]([C:37]([OH:39])=[O:38])=[C:32]([CH:35]=[CH2:36])[CH2:33][S:34][C@H:29]12.C[Si](CC(N)=O)(C)C>O1CCCC1.C(OCC)(=O)C.O.CN(C)C=O>[Cl:12][CH2:13][C:14](=[O:26])[C:15](=[N:19][O:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[C:16]([NH:27][CH:28]1[C:40](=[O:41])[N:30]2[C:31]([C:37]([OH:39])=[O:38])=[C:32]([CH:35]=[CH2:36])[CH2:33][S:34][C@H:29]12)=[O:18]

Komponenten

10

Edukt 5

HCID 24813Phosphorus oxychlorideHCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 128180067-Amino-3vinyl-3-cephem-4-carboxylic acidHCID 248204364-Chloro-2-[(2-methoxy-2-oxoethoxy)imino]-3-oxobutanoic acid

Produkt 1

HCID 131714060HCID 131714060, VerbindungAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Vilsmeier reagent prepared from N,N-dimethylformamide (3.76 ml) and phosphorus oxychloride (4.46 ml) was suspended in dry tetrahydrofuran (50 ml). To the suspension was added 4-chloro-2-methoxycarbonylmethoxyimino-3-oxobutyric acid (syn isomer) (10.5 g), and the mixture was stirred under ice-cooling to prepare the activated acid solution. This solution was added at a time to a solution of 7-amino-3-vinyl-3-cephem-4-carboxylic acid (10 g) and trimethylsilylacetamide (35 g) in ethyl acetate (110 ml) at -30° C. After the reaction mixture was stirred at -15° C. for an hour, the resultant solution was poured into water (100 ml) and then extracted with ethyl acetate (200 ml). The extract was washed with a saturated aqueous sodium chloride and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was triturated with diisopropyl ether to give 7-(4-chloro-2-methoxycarbonylmethoxyimino-3-oxobutyramido)-3-vinyl-3-cephem-4-carboxylic acid (syn isomer) (16.75 g).

Aufarbeitung

  1. temperaturecooling
  2. customto prepare the activated acid solution
  3. stirringAfter the reaction mixture was stirred at -15° C. for an hour
  4. extractionextracted with ethyl acetate (200 ml)
  5. washThe extract was washed with a saturated aqueous sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was triturated with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-4fddd52f64f94f689b9b6d6a9e648490
Quelldatensatz
uspto-grants-1988_03
Patentnummer
US04731443

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