Sulfuric Acid → Clavulanic Acid

HRID 862875Notes

Reaction equation

HRID 862875 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 two times 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).

Workup

  1. customthe water layer separated
  2. extractiontwo times 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-a570d6451b4c48ef9134fc78940cf195
Source dataset
uspto-grants-1998_02
Patent number
US05719277

Reaction notes

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