Hydrochloric Acid → HCID 131713365, compound

HRID 2296009Notes

Reaction equation

HRID 2296009 reaction equation
Cl.[CH3:2][S:3][CH2:4][O:5][N:6]=[C:7]([C:30]1[N:31]=[C:32]([NH:36]C=O)[S:33][C:34]=1[Cl:35])[C:8]([NH:10][CH:11]1[C:28](=[O:29])[N:13]2[C:14]([C:25]([O-:27])=[O:26])=[C:15]([CH2:18][N+:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:16][S:17][C@H:12]12)=[O:9]>CO>[CH3:2][S:3][CH2:4][O:5][N:6]=[C:7]([C:30]1[N:31]=[C:32]([NH2:36])[S:33][C:34]=1[Cl:35])[C:8]([NH:10][CH:11]1[C:28](=[O:29])[N:13]2[C:14]([C:25]([O-:27])=[O:26])=[C:15]([CH2:18][N+:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:16][S:17][C@H:12]12)=[O:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131713367HCID 131713367, compound

Product 1

HCID 131713365HCID 131713365, compoundYield 63.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Conc. hydrochloric acid (1.5 g) was added to the mixture of 7-[2-methylthiomethoxyimino-2-(2-formamido-5-chlorothiazol-4-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (2.8 g) and methanol (30 ml), and stirred at ambient temperature for 5 hours. After removal of solvent, and the residue was dissolved in water and the solution was adjusted to pH 4.0 with 10% aqueous sodium hydroxide under ice-cooling. The solution was subjected to column chromatography on macroporus non-ionic adsorption resin "Diaion HP-20" and eluted with 20% aqueous solution of isopropyl alcohol. The fractions containing the object compound were collected and concentrated and lyophilized to give 7-[2-methylthiomethoxyimino-2-(2-amino-5-chlorothiazol-4-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (1.7 g).

Workup

  1. customAfter removal of solvent
  2. dissolutionthe residue was dissolved in water
  3. temperaturecooling
  4. washeluted with 20% aqueous solution of isopropyl alcohol
  5. additionThe fractions containing the object compound
  6. customwere collected
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-95dc5c96bd4e494c961d5abc7ea9004a
Source dataset
uspto-grants-1984_01
Patent number
US04427677

Reaction notes

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