Hydrochloric Acid → HCID 131714969, compound

HRID 1731706Notes

Reaction equation

HRID 1731706 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:24]1[N:25]=[C:26]([NH:29]C(=O)C(F)(F)F)[S:27][CH:28]=1)[C:5]([NH:7][CH:8]1[C:22](=[O:23])[N:10]2[C:11]([C:19]([OH:21])=[O:20])=[C:12]([CH2:15][S:16][CH:17]=[CH2:18])[CH2:13][S:14][C@H:9]12)=[O:6].C([O-])(=O)C.[Na+].[ClH:41]>O>[ClH:41].[NH2:29][C:26]1[S:27][CH:28]=[C:24]([C:4](=[N:3][O:2][CH3:1])[C:5]([NH:7][CH:8]2[C:22](=[O:23])[N:10]3[C:11]([C:19]([OH:21])=[O:20])=[C:12]([CH2:15][S:16][CH:17]=[CH2:18])[CH2:13][S:14][C@H:9]23)=[O:6])[N:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 517045Sodium AcetateHCID 131714967HCID 131714967, compound

Product 1

HCID 131714969HCID 131714969, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 7-[2-methoxyimino-2-{2-(2,2,2-trifluoroacetamido)thiazol-4-yl}acetamido]-3-vinylthiomethyl-3-cephem-4-carboxylic acid (syn isomer) (380 mg) and sodium acetate (937 mg) in water (8 ml) was stirred at ambient temperature overnight. The mixture was adjusted to pH 1.6 with 6N-hydrochloric acid. This solution was subjected to column chormatography on macroporous non-ionic adsorption resin "Diaion HP 20" (15 ml). After the column was washed with water, the elution was carried out with 25% aqueous isopropyl alcohol. The eluates containing the object compound were collected, evaporated to remove isopropyl alcohol under reduced pressure and lyophilized to give 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-vinylthiomethyl-3-cephem-4-carboxylic acid hydrochloride (syn isomer) (170 mg).

Workup

  1. washAfter the column was washed with water
  2. washthe elution
  3. additionThe eluates containing the object compound
  4. customwere collected
  5. customevaporated
  6. customto remove isopropyl alcohol under reduced pressure

Sources & evidence

ORD record
ord-89b58712fb694cd092a74086785a79f6
Source dataset
uspto-grants-1986_11
Patent number
US04622318

Reaction notes

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