1,4-Dioxane → HCID 131712685, compound

HRID 2058689Notes

Reaction equation

HRID 2058689 reaction equation
[OH:1][CH:2]([CH:4]1[C:10](=[O:11])[N:9]2[CH:5]1[CH2:6][C:7]([O:22][S:23]([C:26]1[C:27]([CH3:32])=[CH:28][CH:29]=[CH:30][CH:31]=1)(=[O:25])=[O:24])=[C:8]2[C:12]([O:14]CC1C=CC=CC=1)=[O:13])[CH3:3].C(=O)(O)[O-].[Na+:37].O1CCOCC1>[Pd].O>[OH:1][CH:2]([CH:4]1[C:10](=[O:11])[N:9]2[CH:5]1[CH2:6][C:7]([O:22][S:23]([C:26]1[C:27]([CH3:32])=[CH:28][CH:29]=[CH:30][CH:31]=1)(=[O:25])=[O:24])=[C:8]2[C:12]([O-:14])=[O:13])[CH3:3].[Na+:37]

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 131712684Benzyl 6-(1-hydroxyethyl)-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]-hept-2-en-7-one-2-carboxylate

Product 1

HCID 131712685HCID 131712685, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of benzyl 6-(1-hydroxyethyl)-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (30 mg), 10% palladium on charcoal (30 mg), sodium bicarbonate (6 mg), dioxane (3 ml) and water (1 ml) is hydrogenated at 40 psi for 30 mins. The mixture is filtered to remove the catalyst which is washed with water (3×3 ml) The combined filtrate is extracted with ethylacetate (3×2 ml), concentrated in vacuo to ca. 2 ml, and lyophilized to give sodium 6-(1-hydroxyethyl)-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 water (3×3 ml) The combined filtrate
  4. extractionis extracted with ethylacetate (3×2 ml)
  5. concentrationconcentrated in vacuo to ca. 2 ml

Sources & evidence

ORD record
ord-39d03c8355a2497ea3ee9a184bbdc2c4
Source dataset
uspto-grants-1982_03
Patent number
US04318912

Reaction notes

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