Trifluoroacetic acid → Trifluoroacetic acid

HRID 1614091Notes

Reaction equation

HRID 1614091 reaction equation
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]

Participants

9

Reactant 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, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 178480381HCID 178480381, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-69d4449b093a42fbb4c0b4cb94855d75
Source dataset
uspto-grants-1993_03
Patent number
US05194432

Reaction notes

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