Hydrochloric Acid → HCID 131716620, compound

HRID 1088058Notes

Reaction equation

HRID 1088058 reaction equation
FC(F)(F)C(O)=O.C([NH:10][C:11]1[S:12][CH:13]=[C:14]([C:16](=[N:43][O:44][CH3:45])[C:17]([NH:19][C@@H:20]2[C:41](=[O:42])[N:22]3[C:23]([C:38]([O-:40])=[O:39])=[C:24]([CH2:27][N+:28]4[N:29]([CH3:37])[C:30]([NH:34]C=O)=[C:31]([CH3:33])[CH:32]=4)[CH2:25][S:26][C@H:21]23)=[O:18])[N:15]=1)=O.Cl.C(OCC)C>CO>[NH2:10][C:11]1[S:12][CH:13]=[C:14]([C:16](=[N:43][O:44][CH3:45])[C:17]([NH:19][C@@H:20]2[C:41](=[O:42])[N:22]3[C:23]([C:38]([O-:40])=[O:39])=[C:24]([CH2:27][N+:28]4[N:29]([CH3:37])[C:30]([NH2:34])=[C:31]([CH3:33])[CH:32]=4)[CH2:25][S:26][C@H:21]23)=[O:18])[N:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 131716622HCID 131716622, compound

Product 1

HCID 131716620HCID 131716620, compoundYield 28.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of trifluoroacetic acid salt of 7β-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-(2,4-dimethyl-3-formamido-1-pyrazolio)methyl-3- cephem-4-carboxylate (syn isomer) (3 g) in methanol (15 ml) was added concentrated hydrochloric acid (1.57 ml) at ambient temperature. After being stirred at the same temperature for 4 hours, the reaction mixture was added dropwise to diethyl ether, and the resulting precipitate was collected by filtration. The precipitate was dissolved in water, and the solution was adjusted to pH 2 with aqueous 5% sodium bicarbonate solution and subjected to column chromatography on macroporous non-ionic adsorption resin "Diaion HP-20". The desired compound was eluted with aqueous 5% isopropyl alcohol solution. The objective fractions were collected and the isopropyl alcohol was evaporated. The resulting aqueous solution was lyophilized to give 7β-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-(3-amino-2,4-dimethyl-1-pyrazolio)methyl-3-cephem-4-carboxylate (syn isomer) (763.5 mg).

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. dissolutionThe precipitate was dissolved in water
  3. washThe desired compound was eluted with aqueous 5% isopropyl alcohol solution
  4. customThe objective fractions were collected
  5. customthe isopropyl alcohol was evaporated

Sources & evidence

ORD record
ord-7f3b36ed56544bb49d11886f0fc4b506
Source dataset
uspto-grants-1990_10
Patent number
US04960766

Reaction notes

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