Sulfuric Acid → Clavulanic Acid

HRID 962892Notes

Reaction equation

HRID 962892 reaction equation
[CH2:1]1[C:4](=[O:5])[N:3]2[C@@H:6]([C:12]([O-:14])=[O:13])/[C:7](/[O:11][C@H:2]12)=[CH:8]/[CH2:9][OH:10].[K+].S(=O)(=O)(O)O>C(OCC)(=O)C>[CH2:1]1[C:4](=[O:5])[N:3]2[C@@H:6]([C:12]([OH:14])=[O:13])/[C:7](/[O:11][C@H:2]12)=[CH:8]/[CH2:9][OH:10]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 23665591Potassium Clavulanate

Product 1

HCID 5280980Clavulanic Acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of potassium clavulanate in ice cold water was stirred with ethyl acetate under cooling with ice-water. With a solution of about 10% (w/w) sulphuric acid the pH was brought at about 2, the water layer separated and twice extracted with ethyl acetate. The collected extracts were dried with magnesium sulphate, filtered and washed with ethyl acetate, yielding a solution of clavulanic acid of about 2% (w/w). The clavulanic acid was diluted with an equal volume of acetone and diamine was added.

Workup

  1. customthe water layer separated
  2. extractiontwice extracted with ethyl acetate
  3. dry with materialThe collected extracts were dried with magnesium sulphate
  4. filtrationfiltered
  5. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-3d8dd5ab54ce4f6f9cdb7df3e7a7fd7f
Source dataset
uspto-grants-1998_06
Patent number
US05760218

Reaction notes

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