Benzyl (3S, 5R)-Penam-3-Carboxylate 1,1-Dioxide → (3S, 5R)-penam-3-carboxylic acid 1,1-dioxide

HRID 1733203Notes

Reaction equation

HRID 1733203 reaction equation
[S:1]1(=[O:20])(=[O:19])[C@@H:5]2[CH2:6][C:7](=[O:8])[N:4]2[C@@H:3]([C:9]([O:11]CC2C=CC=CC=2)=[O:10])[CH2:2]1.[H][H]>CO.C(OCC)(=O)C.[Pd]>[S:1]1(=[O:20])(=[O:19])[C@@H:5]2[CH2:6][C:7](=[O:8])[N:4]2[C@@H:3]([C:9]([OH:11])=[O:10])[CH2:2]1

Participants

6

Reactant 2

HCID 131711968Benzyl (3S, 5R)-Penam-3-Carboxylate 1,1-DioxideHCID 178418361HCID 178418361, compound

Product 1

HCID 13518352(3S, 5R)-penam-3-carboxylic acid 1,1-dioxide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 131 mg of benzyl (3S, 5R)-penam-3-carboxylate 1,1-dioxide in a mixture of 15 ml of methanol and 10 ml of ethyl acetate was added 100 mg of 10% palladium on carbon. The mixture was stirred under an atmosphere of hydrogen at atmospheric pressure until hydrogen uptake ceased. At this point, the reaction mixture was filtered and the solvent was removed by evaporation in vacuo. This afforded 106 mg of the title compound [alpha]D25 =203 (CH3OH; C=1). The NMR spectrum (60 MHz; D2O) showed absorptions at 4.85 (m, 1H), 4.82 (m, 1H), 3.85 (m, 2H) and 3.43 (m, 2H) ppm. The IR spectrum (film) showed absorptions at 1760 and 1730 cm-1.

Workup

  1. filtrationAt this point, the reaction mixture was filtered
  2. customthe solvent was removed by evaporation in vacuo

Sources & evidence

ORD record
ord-b10f58fac83d496dbd4b68c0ee38dfa8
Source dataset
uspto-grants-1980_12
Patent number
US04241050

Reaction notes

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