Water → Sulbactam

HRID 354916Notes

Reaction equation

HRID 354916 reaction equation
[CH3:1][C:2]1([CH3:15])[S:6](=[O:8])(=[O:7])[CH:5]2[CH2:9][C:10](=[O:11])[N:4]2[CH:3]1[C:12]([O-:14])=[O:13].[Na+].O.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:15])[S:6](=[O:7])(=[O:8])[C@@H:5]2[CH2:9][C:10](=[O:11])[N:4]2[C@H:3]1[C:12]([OH:14])=[O:13]

Participants

7

Reactant 4

HCID 962WaterHCID 24436Sodium SulfateHCID 516892Sodium BicarbonateHCID 23691718Sodium penicillanate 1,1-dioxide

Product 1

HCID 130313Sulbactam

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6212ChloroformSolvent

Procedure

To a stirred solution of 2.55 g. of sodium penicillanate 1,1-dioxide in 20 ml. of water was added 3.80 g. of tetrabutylammonium bisulfate. Stirring was continued for 5 minutes and then 20 ml. of chloroform was added. The pH was adjusted to 6.8 with saturated aqueous sodium bicarbonate and then the aqueous layer was saturated with sodium sulfate. The layers were separated and the aqueous layer was extracted with chloroform. The combined chloroform solutions were dried using sodium sulfate and then evaporated in vacuo to give the tetrabutylammonium salt of penicillanic acid 1,1-dioxide.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with chloroform
  3. dry with materialThe combined chloroform solutions were dried
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-ac2e53e3cddb465cb06bb2f8c3814586
Source dataset
uspto-grants-1983_03
Patent number
US04377590

Reaction notes

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