Sodium Bicarbonate → Clavulanic Acid

HRID 1004746Notes

Reaction equation

HRID 1004746 reaction equation
[CH2:1]1[C:4](=[O:5])[N:3]2[C@@H:6]([C:12]([O:14]CC3C=CC=CC=3)=[O:13])/[C:7](/[O:11][C@H:2]12)=[CH:8]/[CH2:9][OH:10].C(=O)([O-])O.[Na+]>C(O)C.[Pd]>[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

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 99040553-(2-Hydroxy-ethylidene)-7-oxo-4-oxa-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester(benzyl calvunlanate)

Product 1

HCID 5280980Clavulanic AcidYield 69.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Substantially pure benzyl clavulanate (281 mg) in ethanol (25 ml.) containing sodium hydrogen carbonate (82 mg.) was hydrogenated over 10% Pd/C (90 mg.) for 25 minutes at room temperature and atmospheric pressure. The catalyst was filtered off, washed with water and ethanol, and the combined filtrates evaporated under reduced pressure at room temperature. The residual semi-solid was triturated with acetone, filtered and washed with ether to yield sodium clavulanate (135 mg.)

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with water and ethanol
  3. customthe combined filtrates evaporated under reduced pressure at room temperature
  4. customThe residual semi-solid was triturated with acetone
  5. filtrationfiltered
  6. washwashed with ether

Sources & evidence

ORD record
ord-95e904219d0c45c691e7b81f879337a0
Source dataset
uspto-grants-2000_04
Patent number
US06051703

Reaction notes

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