Hydrochloric Acid → HCID 131711619, compound

HRID 1388424Notes

Reaction equation

HRID 1388424 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-ae18fb0f650349f89ecb0302c182106b
Source dataset
uspto-grants-1984_02
Patent number
US04431643

Reaction notes

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