Hydrochloric Acid → HCID 88745700, compound

HRID 2285642Notes

Reaction equation

HRID 2285642 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][C@@H:10]1[C:28](=[O:29])[N:12]2[C:13]([C:25]([OH:27])=[O:26])=[C:14]([CH2:17]OC(=O)CC(=O)C)[CH2:15][S:16][C@H:11]12)=[O:8].[S:30]([O-:33])([O-:32])=[O:31].[Na+:34].[Na+:35].Cl>O1CCCC1.O>[Na:34][Na:35].[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][C@@H:10]1[C:28](=[O:29])[N:12]2[C:13]([C:25]([OH:27])=[O:26])=[C:14]([CH2:17][S:30]([OH:33])(=[O:32])=[O:31])[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 24437Sodium SulfiteHCID 70541620HCID 70541620, compound

Product 2

HCID 141233DisodiumHCID 88745700HCID 88745700, compoundYield 37.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

In a mixture of tetrahydrofuran (5 ml) and water (10 ml) were dissolved 7β-(2-thienylacetamido)-3-(3-oxobutyryloxy)methyl-3-cephem-4-carboxylic acid (876 mg) and sodium sulfite (504 mg) and the resultant solution was stirred for 120 minutes at 60° C. To the reaction mixture was added water (10 ml) and the mixture was adjusted its pH to 7.2 with 2N-HCl, followed by condensation under reduced pressure. The residue was subjected to column-chromatography of silica-gel and eluted with acetonitrile-water (7:1-5:1). The fractions containing the objective compound were combined and the mixture was subjected to distillation of acetonitrile. The residue was chromatographed on column packed with Amberlite XAD-2 and eluted with water and then water-methanol. The fractions containing the objective compound were combined and the mixture was condensed under reduced pressure, followed by freeze-drying to give disodium salt of 7β-(2-thienylacetamido)-3-sulfomethyl-3-cephem-4-carboxylic acid (310 mg).

Workup

  1. customfollowed by condensation under reduced pressure
  2. washeluted with acetonitrile-water (7:1-5:1)
  3. additionThe fractions containing the objective compound
  4. distillationthe mixture was subjected to distillation of acetonitrile
  5. customThe residue was chromatographed on column
  6. washeluted with water
  7. additionThe fractions containing the objective compound
  8. customcondensed under reduced pressure
  9. customby freeze-drying

Sources & evidence

ORD record
ord-f3cfaf59b0d444c5b50c06d5494fc2e2
Source dataset
uspto-grants-1982_04
Patent number
US04323676

Reaction notes

Loading…