Hydrochloric Acid → HCID 131716624, compound

HRID 1088059Notes

Reaction equation

HRID 1088059 reaction equation
Cl.[NH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8](=[N:34][O:35][CH3:36])[C:9]([NH:11][C@@H:12]2[C:32](=[O:33])[N:14]3[C:15]([C:29]([O-:31])=[O:30])=[C:16]([CH2:19][N+:20]4[N:21]([CH3:28])[C:22]([NH:25]C=O)=[CH:23][CH:24]=4)[CH2:17][S:18][C@H:13]23)=[O:10])[N:7]=1.C(OCC)C>CO>[NH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8](=[N:34][O:35][CH3:36])[C:9]([NH:11][C@@H:12]2[C:32](=[O:33])[N:14]3[C:15]([C:29]([O-:31])=[O:30])=[C:16]([CH2:19][N+:20]4[N:21]([CH3:28])[C:22]([NH2:25])=[CH:23][CH:24]=4)[CH2:17][S:18][C@H:13]23)=[O:10])[N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 131716626HCID 131716626, compound

Product 1

HCID 131716624HCID 131716624, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Concentrated hydrochloric acid (0.136 ml) was added to a suspension of 7β-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-(3-formamido-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate (syn isomer) (0.2 g) in methanol (1 ml) at ambient temperature. After being stirred at the same temperature for 3 hours, the mixture was added dropwise to diethyl ether (100 ml), and the precipitate was collected by filtration. The precipitate was dissolved in water and subjected to column chromatography on macroporous non-ionic adsorption resin "Diaion HP-20". The desired product was eluted with water, and lyophilized to give 7β-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-(3-amino-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate.trihydrochloride (syn isomer) (71.20 mg).

Workup

  1. filtrationthe precipitate was collected by filtration
  2. dissolutionThe precipitate was dissolved in water
  3. washThe desired product was eluted with water

Sources & evidence

ORD record
ord-a86c3e1333b246c0a1b6528371c7124b
Source dataset
uspto-grants-1990_10
Patent number
US04960766

Reaction notes

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