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

HRID 1105862Notes

Reaction equation

HRID 1105862 reaction equation
[Cl:1][C:2]1[CH2:8][CH:7]2[N:4]([C:5](=[O:9])[CH2:6]2)[C:3]=1[C:10]([O:12]CC1C=CC=CC=1)=[O:11].C(=O)(O)[O-].[Na+:24].C>CO.O.[Pd]>[Cl:1][C:2]1[CH2:8][CH:7]2[N:4]([C:5](=[O:9])[CH2:6]2)[C:3]=1[C:10]([O-:12])=[O:11].[Na+:24]

Participants

7

Reactant 3

HCID 297MethaneHCID 516892Sodium BicarbonateHCID 12804728Benzyl 3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2carboxylate

Product 1

HCID 23672728Sodium 3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Benzyl 3-chloro-1azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (28 mg) in methanol (2.5 ml) and water (0.5 ml) containing sodium bicarbonate (8.5 ml) is hydrogenated with 10% palladium on powdered charcoal (30 mg) at 40 psi for 30 minutes. The mixture is filtered and the catalyst is washed with water (5 ml). The combined filtrate is concentrated in vacuo to 1/2 its volume, washed with ethylacetate, and lyophilized to provide sodium 3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Workup

  1. filtrationThe mixture is filtered
  2. washthe catalyst is washed with water (5 ml)
  3. concentrationThe combined filtrate is concentrated in vacuo to 1/2 its volume
  4. washwashed with ethylacetate

Sources & evidence

ORD record
ord-7259b4d899b34af1a6789e283ddcee46
Source dataset
uspto-grants-1982_01
Patent number
US04310538

Reaction notes

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