Hydrochloric Acid →

HRID 1380981Notes

Reaction equation

HRID 1380981 reaction equation
I.[CH2:2]([O:4][N:5]=[C:6]([C:32]1[N:36]=[C:35]([NH2:37])[S:34][N:33]=1)[C:7]([NH:9][CH:10]1[C:30](=[O:31])[N:12]2[C:13]([C:27]([O-:29])=[O:28])=[C:14]([CH:17]=[CH:18][S:19][CH2+:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]3[CH3:26])[CH2:15][S:16][C@H:11]12)=[O:8])[CH3:3].Cl>C(=O)(O)[O-].[Na+]>[CH2:2]([O:4][N:5]=[C:6]([C:32]1[N:36]=[C:35]([NH2:37])[S:34][N:33]=1)[C:7]([NH:9][CH:10]1[C:30](=[O:31])[N:12]2[C:13]([C:27]([O-:29])=[O:28])=[C:14]([CH:17]=[CH:18][S:19][CH2+:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]3[CH3:26])[CH2:15][S:16][C@H:11]12)=[O:8])[CH3:3]

Participants

2

Reactant 1

HCID 313Hydrochloric Acid

Product 0

No Product data yet.

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

7-[2-Ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-[2-(1-methyl-2-pyridinio)thiovinyl]-3-cephem-4-carboxylate hydriodide (syn isomer) (trans isomer) (2.0 g) was dissolved in a saturated aqueous solution of sodium bicarbonate. After being adjusted to pH 5.5 with 10% aqueous hydrochloric acid, the solution was filtered to remove undissolved compound. The filtrate was purified by column chromatography on macroporous non-ionic adsorption resin "Diaion HP-20" and eluted with 30% aqueous solution of isopropyl alcohol. The fractions, containing the desired compound, were combined, concentrated in vacuo and lyophilized to give 7-[2-ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-[2-(1-methyl-2-pyridinio)thiovinyl]-3-cephem-4-carboxylate (syn isomer) (trans isomer) (0.8 g).

Workup

  1. filtrationthe solution was filtered
  2. customto remove undissolved compound
  3. customThe filtrate was purified by column chromatography on macroporous non-ionic adsorption resin "Diaion HP-20"
  4. washeluted with 30% aqueous solution of isopropyl alcohol
  5. additionThe fractions, containing the desired compound
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f2772e00ce894b5f96c8005fe0f9bb92
Source dataset
uspto-grants-1986_04
Patent number
US04584290

Reaction notes

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