Hydrochloric Acid → HCID 131714389, compound

HRID 464949Notes

Reaction equation

HRID 464949 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:30]1[N:31]=[C:32]([NH:35]C=O)[S:33][CH:34]=1)[C:5]([NH:7][CH:8]1[C:28](=[O:29])[N:10]2[C:11]([C:25]([O-:27])=[O:26])=[C:12]([CH2:15][N+:16]3[CH:21]=[CH:20][CH:19]=[C:18]([NH:22]C=O)[CH:17]=3)[CH2:13][S:14][C@H:9]12)=[O:6].Cl>CO>[CH3:1][O:2][N:3]=[C:4]([C:30]1[N:31]=[C:32]([NH2:35])[S:33][CH:34]=1)[C:5]([NH:7][CH:8]1[C:28](=[O:29])[N:10]2[C:11]([C:25]([O-:27])=[O:26])=[C:12]([CH2:15][N+:16]3[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=3)[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131714391HCID 131714391, compound

Product 1

HCID 131714389HCID 131714389, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 7-[2-methoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(3-formamido-1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (4.4 g) and conc. hydrochloric acid (1.6 ml) in methanol was stirred for 4 hours at room temperature and evaporated to dryness. The residue was dissolved in water (100 ml) and subjected to column chromatography on a non ionic adsorption resin "Diaion HP 20" (160 ml). After the column was washed with water, the elution was carried out with 20% aqueous methanol. The fractions containing an object compound were collected, evaporated to remove methanol under reduced pressure and lyophilized to give 7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(3-amino-1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (2.3 g), mp 185° to 189° C. (dec.).

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in water (100 ml)
  3. washAfter the column was washed with water
  4. washthe elution
  5. additionThe fractions containing an object compound
  6. customwere collected
  7. customevaporated
  8. customto remove methanol under reduced pressure

Sources & evidence

ORD record
ord-d278e19afa3e40649016da40527cebdf
Source dataset
uspto-grants-1985_10
Patent number
US04550102

Reaction notes

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