Potassium Bicarbonate → HCID 70480354, compound

HRID 1733201Notes

Reaction equation

HRID 1733201 reaction equation
[S:1]1(=[O:13])(=[O:12])[C@@H:5]2[CH2:6][C:7](=[O:8])[N:4]2[CH:3]([C:9]([O-:11])=[O:10])[CH2:2]1.C(=O)(O)[O-].[K+].[H][H]>CO.[Pd]>[S:1]1(=[O:13])(=[O:12])[C@@H:5]2[CH2:6][C:7](=[O:8])[N:4]2[CH:3]([C:9]([OH:11])=[O:10])[CH2:2]1

Participants

6

Reactant 3

HCID 516893Potassium BicarbonateHCID 86737397HCID 86737397, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70480354HCID 70480354, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 350 mg of benzyl (3S, 5R and 3R, 5S)penam-3-carboxylate 1,1-dioxide in 12 ml of methanol was added 75 mg of potassium bicarbonate followed by 350 mg of 10% palladium on carbon. The mixture was shaken under an atmosphere of hydrogen at atmospheric pressure until hydrogen absorption ceased. The catalyst was removed by filtration and then the solvent was removed by evaporation in vacuo. The residue was partitioned between water and ethyl acetate at pH 8. The aqueous layer was removed, and the pH was lowered to 1.5. The acidic aqueous phase was extracted liberally with ethyl acetate. The ethyl acetate extracts were combined, dried (Na2SO4) and concentrated in vacuo. The residue was recrystallized from ethyl acetate-methanol, to give 41 mg of the title compound, mp 164°-167° C. The NMR spectrum (100 MHz; DMSO-d6) showed absorptions at 4.97 (m, 1H), 4.86 (q, 1H), 3.90 (m, 2H) and 3.65 (m, 2H) ppm. The IR spectrum (film) showed absorptions at 1770 and 1725 cm-1. The product had no optical activity.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was removed by evaporation in vacuo
  3. customThe residue was partitioned between water and ethyl acetate at pH 8
  4. customThe aqueous layer was removed
  5. extractionThe acidic aqueous phase was extracted liberally with ethyl acetate
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was recrystallized from ethyl acetate-methanol

Sources & evidence

ORD record
ord-efcf12dea007477ebb92e25a9e4895e0
Source dataset
uspto-grants-1980_12
Patent number
US04241050

Reaction notes

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