Hydrochloric Acid → HCID 131714233, compound

HRID 1247927Notes

Reaction equation

HRID 1247927 reaction equation
[CH2:1]([O:3][N:4]=[C:5]([C:32]1[N:36]=[C:35]([NH2:37])[S:34][N:33]=1)[C:6]([NH:8][CH:9]1[C:30](=[O:31])[N:11]2[C:12]([C:27]([O-:29])=[O:28])=[C:13]([CH2:16][N+:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N:23](C)[CH:24]=O)[CH:18]=3)[CH2:14][S:15][C@H:10]12)=[O:7])[CH3:2].Cl>CO>[CH2:1]([O:3][N:4]=[C:5]([C:32]1[N:36]=[C:35]([NH2:37])[S:34][N:33]=1)[C:6]([NH:8][CH:9]1[C:30](=[O:31])[N:11]2[C:12]([C:27]([O-:29])=[O:28])=[C:13]([CH2:16][N+:17]3[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][CH3:24])[CH:18]=3)[CH2:14][S:15][C@H:10]12)=[O:7])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131714235HCID 131714235, compound

Product 1

HCID 131714233HCID 131714233, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 7-[2-ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-[3-(N-methylformamido)-1-pyridiniomethyl]-3-cephem-4-carboxylate (syn isomer) (2.75 g) in methanol (27.5 ml) was added concentrated hydrochloric acid (1.39 ml) and the mixture was stirred for 75 minutes. The solvent was evaporated and the residue was triturated in acetone. The obtained powder was suspended in water (70 ml), adjusted to pH 4 to 5 with aqueous solution of sodium bicarbonate and subjected to column chromatography on a non ionic adsorption resin "Diaion HP 20" (Trademark: Prepared by Mitsubishi Chemical Industries) (100 ml). After the column was washed with water, the elution was carried out with 15% aqueous isopropyl alcohol. The eluates containing an object compound were collected, evaporated to remove isopropyl alcohol under reduced pressure and lyophilized to give 7-[2-ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-(3-methylamino-1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (1.41 g), mp 149° to 157° C. (dec.).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was triturated in acetone
  3. customsubjected to column chromatography on a non ionic adsorption resin "Diaion HP 20" (Trademark: Prepared by Mitsubishi Chemical Industries) (100 ml)
  4. washAfter the column was washed with water
  5. washthe elution
  6. additionThe eluates containing an object compound
  7. customwere collected
  8. customevaporated
  9. customto remove isopropyl alcohol under reduced pressure

Sources & evidence

ORD record
ord-350ed607d19c4f44b82f336c605f667b
Source dataset
uspto-grants-1985_06
Patent number
US04521413

Reaction notes

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