Hydrochloric Acid → HCID 131716529, compound

HRID 1710283Notes

Reaction equation

HRID 1710283 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:35][O:36][CH:37]([F:39])[F:38])[C:8]([NH:10][C@@H:11]2[C:33](=[O:34])[N:13]3[C:14]([C:30]([O-:32])=[O:31])=[C:15]([CH2:18][N+:19]4[N:20]([CH2:27][CH2:28][OH:29])[C:21]([NH:24]C=O)=[CH:22][CH:23]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.Cl.C(OCC)(=O)C>CO>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:35][O:36][CH:37]([F:38])[F:39])[C:8]([NH:10][C@@H:11]2[C:33](=[O:34])[N:13]3[C:14]([C:30]([O-:32])=[O:31])=[C:15]([CH2:18][N+:19]4[N:20]([CH2:27][CH2:28][OH:29])[C:21]([NH2:24])=[CH:22][CH:23]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 131716531HCID 131716531, compound

Product 1

HCID 131716529HCID 131716529, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 7β-[2-(2-aminothiazol-4-yl)-2(difluoromethoxyimino)acetamido]-3-[3-formamido-2-(2-hydroxyethyl)-1-pyrazolio]methyl-3-cephem-4-carboxylate (syn isomer) (0.7 g) in methanol (3.5 ml) was added concentrated hydrochloric acid (0.42 ml) at ambient temperature. After being stirred at the same temperature for 2 hours, the mixture was poured into ethyl acetate. The resulting precipitate was collected by filtration. The precipitate was dissolved in water, and adjusted to pH 2 with 5% aqueous sodium bicarbonate solution. This solution was subjected to a column chromatography on macroporous non-ionic adsorption resin "Diaion HP20". The object compound was eluted with 10% diisopropyl alcohol, and lyophilized to give 7β-[2-(2-aminothiazol-4-yl)-2-(difluoromethoxyimino)acetamido]-3-[3-amino-2-(2-hydroxyethyl)-1-pyrazolio]methyl-3-cephem-4-carboxylate (syn isomer) (0.41 g).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. dissolutionThe precipitate was dissolved in water
  3. washThe object compound was eluted with 10% diisopropyl alcohol

Sources & evidence

ORD record
ord-804d45b7f4f04eca93f86a6a6dd21599
Source dataset
uspto-grants-1990_08
Patent number
US04952578

Reaction notes

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