Hydrochloric Acid → HCID 131713127, compound

HRID 647121Notes

Reaction equation

HRID 647121 reaction equation
[CH2:1]([O:3][N:4]=[C:5]([C:31]1[N:36]=[C:35]([NH2:37])[CH:34]=[CH:33][N:32]=1)[C:6]([NH:8][CH:9]1[C:29](=[O:30])[N:11]2[C:12]([C:26]([O-:28])=[O:27])=[C:13]([CH2:16][N+:17]3[CH:22]=[CH:21][CH:20]=[C:19]([NH:23]C=O)[CH:18]=3)[CH2:14][S:15][C@H:10]12)=[O:7])[CH3:2].Cl.C(=O)(O)[O-].[Na+]>CO>[CH2:1]([O:3][N:4]=[C:5]([C:31]1[N:36]=[C:35]([NH2:37])[CH:34]=[CH:33][N:32]=1)[C:6]([NH:8][CH:9]1[C:29](=[O:30])[N:11]2[C:12]([C:26]([O-:28])=[O:27])=[C:13]([CH2:16][N+:17]3[CH:22]=[CH:21][CH:20]=[C:19]([NH2:23])[CH:18]=3)[CH2:14][S:15][C@H:10]12)=[O:7])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 131713129HCID 131713129, compound

Product 1

HCID 131713127HCID 131713127, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 7-[2-ethoxyimino-2-(4-aminopyrimidin-2-yl)acetamido]-3-(3-formamido-1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (430 mg) and concentrated hydrochloric acid (0.16 ml) in methanol (4.3 ml) was stirred for 2 hours at room temperature. The mixture was adjusted to pH 4 with aqueous sodium bicarbonate and evaporated under reduced pressure. The residue was dissolved in water (50 ml) and subjected to column chromatography on a non ionic adsorption resin "HP-20" (70 ml). After the column was washed with water, the elution was carried out with 25% aqueous methanol. The eluate was evaporated to remove methanol under reduced pressure and lyophilized to give 7-[2-ethoxyimino-2-(4-aminopyrimidin-2-yl)acetamido]-3-(3-amino-1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (0.22 g), mp 140° to 145° C. (dec.).

Workup

  1. customevaporated under reduced pressure
  2. dissolutionThe residue was dissolved in water (50 ml)
  3. washAfter the column was washed with water
  4. washthe elution
  5. customThe eluate was evaporated
  6. customto remove methanol under reduced pressure

Sources & evidence

ORD record
ord-3aa732d8f2bf42219353ede5d6a9944e
Source dataset
uspto-grants-1983_10
Patent number
US04407798

Reaction notes

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