Trifluoroacetic acid → Trifluoroacetic acid

HRID 1088066Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1088066
P(Cl)(Cl)(Cl)=O.C[N+](C)=CCl.[Cl-].[CH:12]([NH:14][C:15]1[S:16][CH:17]=[C:18]([C:20](=[N:24][O:25][CH:26]2[CH2:30][CH2:29][CH:28]=[CH:27]2)[C:21]([OH:23])=O)[N:19]=1)=[O:13].[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34].[NH2:38][C@@H:39]1[C:56](=[O:57])[N:41]2[C:42]([C:53]([O-:55])=[O:54])=[C:43]([CH2:46][N+:47]3[N:48]([CH3:52])[CH:49]=[CH:50][CH:51]=3)[CH2:44][S:45][C@H:40]12.C(OC(C)C)(C)C>C(OCC)(=O)C>[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34].[CH:12]([NH:14][C:15]1[S:16][CH:17]=[C:18]([C:20](=[N:24][O:25][CH:26]2[CH2:30][CH2:29][CH:28]=[CH:27]2)[C:21]([NH:38][C@@H:39]2[C:56](=[O:57])[N:41]3[C:42]([C:53]([O-:55])=[O:54])=[C:43]([CH2:46][N+:47]4[N:48]([CH3:52])[CH:49]=[CH:50][CH:51]=4)[CH2:44][S:45][C@H:40]23)=[O:23])[N:19]=1)=[O:13]

Komponenten

9

Edukt 6

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 24813Phosphorus oxychlorideHCID 77311Chloro-N,N-dimethylformiminium chloride2×HCID 538228722-(2-Cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetic acidHCID 178480378HCID 178480378, Verbindung

Produkt 2

HCID 6422Trifluoroacetic acidHCID 178480381HCID 178480381, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

N,N-Dimethylformamido (0.75 g) and phosphoryl chloride (1.57 ml) were mixed to prepare Vilsmeier reagent in a usual manner, and the resultant Vilsmeier reagent was suspended in dry ethyl acetate (22 ml). To the suspension was added 2-(2-formamidothiazol-4-yl)-2-(2-cyclopenten-1-yloxyimino) acetic acid (A isomer) (syn isomer) (2.3 g) under ice-cooling with stirring, and then the mixture was stirred for an hour to prepare an activated acid solution. To a solution of bis(trifluoroacetic acid )salts of 7β-amino-3-(2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate (4.7 g) and N-mono(trimethylsilyl)acetamido (11.8 g) in ethyl acetate (50 ml) was added the activated acid solution prepared above at 3° C. After stirring at the same temperature for an hour, the mixture was poured into diisopropyl ether (500 ml). The precipitates were collected by filtration and successively washed with diisopropyl ether to give trifluoroacetic acid salt of 7β-[2-(2-formamidothiazol-4-yl)-2-(2-cyclopenten-1-yloxyimino)acetamido]-3-(2-methyl-1-pyrazolio)methyl- 3-cephem-4-carboxylate (A isomer) (syn isomer) (6.02 g).

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred for an hour
  3. customto prepare an activated acid solution
  4. customprepared above at 3° C
  5. stirringAfter stirring at the same temperature for an hour
  6. filtrationThe precipitates were collected by filtration
  7. washsuccessively washed with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-0361a0995f5e47e8a19a2cf90650f929
Quelldatensatz
uspto-grants-1990_10
Patentnummer
US04960766

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