Hydrochloric Acid → HCID 178502817, compound

HRID 1614080Notes

Reaction equation

HRID 1614080 reaction equation
FC(F)(F)C(O)=O.C([NH:10][C:11]1[S:12][CH:13]=[C:14]([C:16](=[N:39][O:40][CH3:41])[C:17]([NH:19][C@@H:20]2[C:37](=[O:38])[N:22]3[C:23]([C:34]([O-:36])=[O:35])=[C:24]([CH2:27][N+:28]4[N:29]([CH3:33])[CH:30]=[CH:31][CH:32]=4)[CH2:25][S:26][C@H:21]23)=[O:18])[N:15]=1)=O.Cl.C(OCC)C>CO>[NH2:10][C:11]1[S:12][CH:13]=[C:14]([C:16](=[N:39][O:40][CH3:41])[C:17]([NH:19][C@@H:20]2[C:37](=[O:38])[N:22]3[C:23]([C:34]([O-:36])=[O:35])=[C:24]([CH2:27][N+:28]4[N:29]([CH3:33])[CH:30]=[CH:31][CH:32]=4)[CH2:25][S:26][C@H:21]23)=[O:18])[N:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 178502816HCID 178502816, compound

Product 1

HCID 178502817HCID 178502817, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of trifluoroacetic acid salt of 7β-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-(2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate (syn isomer, 2.2 g) in methanol (11 ml) was added conc. hydrochloric acid (0.78 ml) at room temperature, and the mixture was stirred at the same temperature for 2 hours. The reaction mixture was added to diethyl ether (300 ml), and the precipitates were collected by filtration. The precipitates were dissolved in water (20 ml) and the solution was adjusted to pH 5 with saturated aqueous solution of sodium bicarbonate. The solution was subjected to column chromatography on macroporous non-ionic adsorption resin "Diaion HP-20" and eluted with 15% aqueous solution of isopropyl alcohol. The fractions containing the object compound were collected and evaporated in vacuo to remove isopropyl alcohol. The solution was lyophilized to give 7β-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-(2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate (syn isomer, 0.78 g).

Workup

  1. filtrationthe precipitates were collected by filtration
  2. dissolutionThe precipitates were dissolved in water (20 ml)
  3. washeluted with 15% aqueous solution of isopropyl alcohol
  4. additionThe fractions containing the object compound
  5. customwere collected
  6. customevaporated in vacuo
  7. customto remove isopropyl alcohol

Sources & evidence

ORD record
ord-b4ef0cad321e4a90b5e8591ccae4bde5
Source dataset
uspto-grants-1993_03
Patent number
US05194432

Reaction notes

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