Cephalothin → HCID 88424855, compound

HRID 1111096Notes

Reaction equation

HRID 1111096 reaction equation
[C:1](O)(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+:14].CC(O[CH2:19][C:20]1[CH2:37][S:36][C@@H:23]2[C@H:24]([NH:27][C:28]([CH2:30][C:31]3[S:35][CH:34]=[CH:33][CH:32]=3)=[O:29])[C:25](=[O:26])[N:22]2[C:21]=1[C:38]([OH:40])=[O:39])=O.[H-].[Na+]>O>[Na+:14].[S:35]1[CH:34]=[CH:33][CH:32]=[C:31]1[CH2:30][C:28]([NH:27][CH:24]1[C:25](=[O:26])[N:22]2[C:21]([C:38]([O-:40])=[O:39])=[C:20]([CH2:19][C:1](=[S:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:37][S:36][C@H:23]12)=[O:29]

Participants

6

Reactant 4

HCID 6024CephalothinHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 178526132HCID 178526132, compound

Product 1

HCID 88424855HCID 88424855, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

Thiobenzoic acid (1.41 g, 10.2 mmol) and sodium bicarbonate (0.857 g, 10.2 mmol) were stirred in 30 ml of H2O and heated to 50° C. The mixture was filtered through silica gel, and the filtrate was added to cephalothin (1.43 g, 3.4 mmol) in 20 ml of H2O. The reaction mixture was stirred for 20 hours at 50° C. 7-Thiophenylacetamido-3-thiobenzoylmethyl-3-cephem-4-carboxylic acid (0.791 g) was collected by filtration. 50 mg of this material was dissolved in DMF (2 ml). Sodium hydride (4.4 mg. 0.11 mmol) was added, and the mixture was stirred for two hours, filtered, and dried under vacuum. The residue was dissolved in water, refiltered and lyophilized to yield pure 7-thiophenylacetamido-3-thiobenzoylmethyl-3-cephem-4-carboxylate sodium salt.

Workup

  1. filtrationThe mixture was filtered through silica gel
  2. filtration7-Thiophenylacetamido-3-thiobenzoylmethyl-3-cephem-4-carboxylic acid (0.791 g) was collected by filtration
  3. dissolution50 mg of this material was dissolved in DMF (2 ml)
  4. stirringthe mixture was stirred for two hours
  5. filtrationfiltered
  6. customdried under vacuum
  7. dissolutionThe residue was dissolved in water

Sources & evidence

ORD record
ord-ec5a53efb7c1476b9604e71c4df27a7e
Source dataset
uspto-grants-1990_12
Patent number
US04978613

Reaction notes

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