Hydrochloric Acid → HCID 131711619, compound

HRID 2352689Notes

Reaction equation

HRID 2352689 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:25]1[N:26]=[C:27]([NH:30]C(=O)C(F)(F)F)[S:28][CH:29]=1)[C:5]([NH:7][CH:8]1[C:23](=[O:24])[N:10]2[C:11]([C:20]([OH:22])=[O:21])=[C:12]([CH2:15][O:16][C:17](=[O:19])[NH2:18])[CH2:13][S:14][C@H:9]12)=[O:6].O.O.O.C([O-])(=O)C.[Na+].[Cl-].[Na+].Cl>O>[CH3:1][O:2][N:3]=[C:4]([C:25]1[N:26]=[C:27]([NH2:30])[S:28][CH:29]=1)[C:5]([NH:7][CH:8]1[C:23](=[O:24])[N:10]2[C:11]([C:20]([OH:22])=[O:21])=[C:12]([CH2:15][O:16][C:17](=[O:19])[NH2:18])[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 23665404Sodium Acetate TrihydrateHCID 131711620HCID 131711620, compound

Product 1

HCID 131711619HCID 131711619, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7-[2-Methoxyimino-2-{2-(2,2,2-trifluoroacetamido)-1,3-thiazol-4-yl}acetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid (syn isomer) (3.5 g.) was suspended in a solution of sodium acetate trihydrate (12.2 g.) in water (30 ml.). The mixture was stirred for 15 hours at ambient temperature. The reaction mixture was saturated with sodium chloride and adjusted to pH 5.0 with conc. hydrochloric acid with stirring and ice-cooling. Precipitating insoluble material was filtered off. The filtrate was adjusted to pH 3.0 with conc. hydrochloric acid and further adjusted to pH 1.5 with 10% hydrochloric acid. Precipitates were collected by filtration and dried to give 7-[2-methoxyimino-2-(2-amino-1,3-thiazol-4-yl)acetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid (syn isomer) (2.1 g.), mp 210° to 220° C. (dec.).

Workup

  1. stirringwith stirring
  2. temperatureice-cooling
  3. filtrationPrecipitating insoluble material was filtered off
  4. customPrecipitates
  5. filtrationwere collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-ff1414d8ee634df3bd6ca78637969b82
Source dataset
uspto-grants-1989_10
Patent number
US04877873

Reaction notes

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