Trifluoroacetic acid → HCID 131713369, compound

HRID 2296010Notes

Reaction equation

HRID 2296010 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13]([CH2:15][O:16][N:17]=[C:18]([C:41]1[N:42]=[C:43]([NH2:47])[S:44][C:45]=1[Cl:46])[C:19]([NH:21][CH:22]1[C:39](=[O:40])[N:24]2[C:25]([C:36]([O-:38])=[O:37])=[C:26]([CH2:29][N+:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:27][S:28][C@H:23]12)=[O:20])=[O:14])(C)(C)C.C(OC(C)C)(C)C>C(Cl)Cl.C1(OC)C=CC=CC=1>[C:13]([CH2:15][O:16][N:17]=[C:18]([C:41]1[N:42]=[C:43]([NH2:47])[S:44][C:45]=1[Cl:46])[C:19]([NH:21][CH:22]1[C:39](=[O:40])[N:24]2[C:25]([C:36]([O-:38])=[O:37])=[C:26]([CH2:29][N+:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:27][S:28][C@H:23]12)=[O:20])([OH:14])=[O:12]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 131713371HCID 131713371, compound

Product 1

HCID 131713369HCID 131713369, compoundYield 38.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

Trifluoroacetic acid (11.2 ml) was added to a solution of 7-[2-t-butoxycarbonylmethoxyimino-2-(2-amino-5-chlorothiazol-4-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (2.8 g) in methylene chloride (6 ml) and anisole (2.8 ml) under ice-cooling, and the mixture was stirred for an hour at ambient temperature. The reaction mixture was added to diisopropyl ether (120 ml) and precipitates were filtered. The precipitates were added to water and adjusted to pH 4.0 with 10% aqueous sodium hydroxide. The resulting solution was subjected to column chromatography on macroporus non-ionic adsorption "Diaion HP-20" and eluted with 15% aqueous solution of isopropyl alcohol. The fractions containing the object compound were collected and concentrated and lyophilized to give 7-[2-carboxymethoxyimino-2-(2-amino-5-chlorothiazol-4-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (0.97 g).

Workup

  1. temperaturecooling
  2. customprecipitates
  3. filtrationwere filtered
  4. additionThe precipitates were added to water
  5. washeluted with 15% aqueous solution of isopropyl alcohol
  6. additionThe fractions containing the object compound
  7. customwere collected
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-033fa143d66948748a5fe6950a1045e6
Source dataset
uspto-grants-1984_01
Patent number
US04427677

Reaction notes

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