3-(2-Hydroxy-ethylidene)-7-oxo-4-oxa-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester(benzyl calvunlanate) → Clavulanic Acid

HRID 2420213Notes

Reaction equation

HRID 2420213 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)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

4

Reactant 1

HCID 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 Acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Benzyl clavulanate (100 mgs) in ethanol (5 ml) was hydrogenated over 10% Pd/C (30 mgs) for 45 minutes at ambient temperature and atmospheric pressure. The catalyst was filtered, washed with ethanol and the combined filtrates were evaporated in vacuo to give clavulanic acid as an unstable, viscous oil (58 mgs). N.m.r. (C5D5N): 3.05(d,l,J=18Hz), 3.60(dd,l,J1 =18Hz, J2 =2.5Hz), 4.75(d,2,J=7.5Hz), 5.58(t,l,J=7.5Hz), 5.66 (S,l), 6.0δ(d,l,J=2.5 Hz)

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with ethanol
  3. customthe combined filtrates were evaporated in vacuo

Sources & evidence

ORD record
ord-0bf94b7d44a84bd9b062c50c2875d585
Source dataset
uspto-grants-1978_08
Patent number
US04110165

Reaction notes

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