Methane → Sodium 3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

HRID 1164339Notes

Reaction equation

HRID 1164339 reaction equation
[C:1]1([CH3:29])[C:2]([S:7]([O:10][C:11]2[CH2:17][CH:16]3[N:13]([C:14](=[O:18])[CH2:15]3)[C:12]=2[C:19]([O:21]CC2C=CC=CC=2)=[O:20])(=[O:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.C.C(=O)(O)[O-].[Na+:35]>O1CCOCC1.O.[Pd]>[C:1]1([CH3:29])[C:2]([S:7]([O:10][C:11]2[CH2:17][CH:16]3[N:13]([C:14](=[O:18])[CH2:15]3)[C:12]=2[C:19]([O-:21])=[O:20])(=[O:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[Na+:35]

Participants

7

Reactant 3

HCID 297MethaneHCID 516892Sodium BicarbonateHCID 131712683Benzyl 3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Product 1

HCID 131712933Sodium 3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of benzyl 3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (30 mg) and 10% palladium on powdered charcoal (25 mg) in dioxane (3 ml) and water (1 ml) containing sodium bicarbonate (7 mg) is hydrogenated at 40 psi for 30 mins. The mixture is filtered to remove the catalyst which is washed with several portions of H2O (3×3 ml). The combined filtrate is washed with ethyl acetate (3×2 ml), concentrated in vacuo to ca. 2 ml, and lyophilized to afford sodium 3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Workup

  1. filtrationThe mixture is filtered
  2. customto remove the catalyst which
  3. washis washed with several portions of H2O (3×3 ml)
  4. washThe combined filtrate is washed with ethyl acetate (3×2 ml)
  5. concentrationconcentrated in vacuo to ca. 2 ml

Sources & evidence

ORD record
ord-15d5c324dd0b435eb1e201425d6613d7
Source dataset
uspto-grants-1983_01
Patent number
US04369187

Reaction notes

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