Sodium Bicarbonate → HCID 131715541, compound

HRID 1253158Notes

Reaction equation

HRID 1253158 reaction equation
[CH3:1][S:2]([C:4]1[S:5][C@@H:6]2[C@@H:23]([CH2:24][CH3:25])[C:22](=[O:26])[N:7]2[C:8]=1[C:9]([O:11]CC1C=CC([N+]([O-])=O)=CC=1)=[O:10])=[O:3].C([O-])(O)=O.[Na+:31]>C1COCC1.CCO.O.[Pd]>[CH3:1][S:2]([C:4]1[S:5][C@@H:6]2[C@@H:23]([CH2:24][CH3:25])[C:22](=[O:26])[N:7]2[C:8]=1[C:9]([O-:11])=[O:10])=[O:3].[Na+:31]

Participants

7

Reactant 2

HCID 516892Sodium BicarbonateHCID 57088416HCID 57088416, compound

Product 1

HCID 131715541HCID 131715541, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of p-nitrobenzyl (5R,6S)-2-methylsulfinyl-6-ethyl-pen-2-em-3-carboxylate (50 mg) in THF (9 ml) is diluted with EtOH (4.5 ml) and H2O (7.0 ml) containing NaHCO3 (10.6 mg). The resulting solution is added to a prereduced mixture of 10% Pd/C (100 mg) in EtOH (4.5 ml) and the resulting mixture is rapidly stirred under a H2 atmosphere for 2 hours. The mixture is filtered to remove the catalyst which is washed with H2O (2×25 ml). The combined filtrate is extracted with Et2O (2×50 ml) concentrated under vacuum to ca. 10 ml volume, and lyophilized to yield the title compound.

Workup

  1. filtrationThe mixture is filtered
  2. customto remove the catalyst which
  3. washis washed with H2O (2×25 ml)
  4. extractionThe combined filtrate is extracted with Et2O (2×50 ml)
  5. concentrationconcentrated under vacuum to ca. 10 ml volume

Sources & evidence

ORD record
ord-540eb3c89af54e47b2dbd1c20e706899
Source dataset
uspto-grants-1988_05
Patent number
US04748162

Reaction notes

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