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

HRID 1164342Notes

Reaction equation

HRID 1164342 reaction equation
[CH3:1][O:2][C:3]1[CH2:9][CH:8]2[N:5]([C:6](=[O:10])[CH2:7]2)[C:4]=1[C:11]([O:13]CC1C=CC=CC=1)=[O:12].C.C(=O)(O)[O-].[Na+:26]>[Pd].O1CCOCC1.O>[CH3:1][O:2][C:3]1[CH2:9][CH:8]2[N:5]([C:6](=[O:10])[CH2:7]2)[C:4]=1[C:11]([O-:13])=[O:12].[Na+:26]

Participants

6

Reactant 3

HCID 297MethaneHCID 516892Sodium BicarbonateHCID 15136299Benzyl 3-methoxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Product 1

HCID 23682169Sodium 3-methoxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A mixture of benzyl 3-methoxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (50 mg) and 10% palladium on powdered charcoal (50 mg) in 1:1 dioxane-H2O (5 ml) containing sodium bicarbonate (12.5 ml) is hydrogenated at 40 psi for 30 mins. The mixture is filtered and the catalyst is washed with more water (5 ml). The combined filtrate is extracted with ethyl acetate, concentrated in vacuo to ca. 2 ml, and lyophilized to yield sodium 3-methoxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Workup

  1. filtrationThe mixture is filtered
  2. washthe catalyst is washed with more water (5 ml)
  3. extractionThe combined filtrate is extracted with ethyl acetate
  4. concentrationconcentrated in vacuo to ca. 2 ml

Sources & evidence

ORD record
ord-4213cff31b454f0eb5770d8a777320a1
Source dataset
uspto-grants-1983_01
Patent number
US04369187

Reaction notes

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