1,4-Dioxane → Sodium 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

HRID 1493477Notes

Reaction equation

HRID 1493477 reaction equation
[F:1][C:2]([F:35])([F:34])[CH:3]([CH:5]1[C:11](=[O:12])[N:10]2[CH:6]1[CH2:7][C:8]([O:23][S:24]([C:27]1[C:28]([CH3:33])=[CH:29][CH:30]=[CH:31][CH:32]=1)(=[O:26])=[O:25])=[C:9]2[C:13]([O:15]CC1C=CC=CC=1)=[O:14])[OH:4].C(=O)(O)[O-].[Na+:40].O1CCOCC1>[Pd].O>[F:35][C:2]([F:1])([F:34])[CH:3]([CH:5]1[C:11](=[O:12])[N:10]2[CH:6]1[CH2:7][C:8]([O:23][S:24]([C:27]1[C:28]([CH3:33])=[CH:29][CH:30]=[CH:31][CH:32]=1)(=[O:26])=[O:25])=[C:9]2[C:13]([O-:15])=[O:14])[OH:4].[Na+:40]

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 131714283Benzyl 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Product 1

HCID 131716904Sodium 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of benzyl 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (26 mg), 10% palladium on charcoal (25 mg), sodium bicarbonate (4.5 mg), dioxane (2 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 several portions of water (3×2 ml). The combined filtrate is extracted with ethyl acetate (2×2 ml), concentrated in vacuo to ca. 2 ml, and lyophilized to provide sodium 6-(2,2,2-trifluoro-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 several portions of water (3×2 ml)
  4. extractionThe combined filtrate is extracted with ethyl acetate (2×2 ml)
  5. concentrationconcentrated in vacuo to ca. 2 ml

Sources & evidence

ORD record
ord-17531c0827354cf788b28e3080571e8f
Source dataset
uspto-grants-1991_06
Patent number
US05021566

Reaction notes

Loading…