Hydrochloric Acid → HCID 131713115, compound

HRID 647118Notes

Reaction equation

HRID 647118 reaction equation
[CH3:1][S:2][CH2:3][O:4][N:5]=[C:6]([C:29]1[N:34]=[C:33]([NH:35]C=O)[CH:32]=[CH:31][N:30]=1)[C:7]([NH:9][CH:10]1[C:27](=[O:28])[N:12]2[C:13]([C:24]([O-:26])=[O:25])=[C:14]([CH2:17][N+:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:15][S:16][C@H:11]12)=[O:8].Cl.C(=O)(O)[O-].[Na+]>CO>[CH3:1][S:2][CH2:3][O:4][N:5]=[C:6]([C:29]1[N:34]=[C:33]([NH2:35])[CH:32]=[CH:31][N:30]=1)[C:7]([NH:9][CH:10]1[C:27](=[O:28])[N:12]2[C:13]([C:24]([O-:26])=[O:25])=[C:14]([CH2:17][N+:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 131713117HCID 131713117, compound

Product 1

HCID 131713115HCID 131713115, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 7-[2-methylthiomethoxyimino-2-(4-formamidopyrimidin-2-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (1.9 g) and concentrated hydrochloric acid (0.7 ml) in methanol (19 ml) was stirred for 1.5 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 (200 ml) and subjected to column chromatography on a non ionic adsorption resin "HP-20" (300 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-methylthiomethoxyimino-2-(4-aminopyrimidin-2-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (1.13 g).

Workup

  1. customevaporated under reduced pressure
  2. dissolutionThe residue was dissolved in water (200 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-e20a8619291e4411a74656ae8b415b36
Source dataset
uspto-grants-1983_10
Patent number
US04407798

Reaction notes

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