Ethanol → HCID 23671966, compound

HRID 2058687Notes

Reaction equation

HRID 2058687 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])[CH:8]2[C:12]([O:14]CC1C=CC=CC=1)=[O:13])[CH3:3].C(O)C.O.C([O-])(O)=O.[Na+:31]>O1CCOCC1.[Pd]>[OH:1][CH:2]([CH:4]1[C:10](=[O:11])[N:9]2[CH:5]1[CH2:6][C:7](=[O:22])[CH:8]2[C:12]([O-:14])=[O:13])[CH3:3].[Na+:31]

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 516892Sodium BicarbonateHCID 12848998HCID 12848998, compound

Product 1

HCID 23671966HCID 23671966, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Benzyl 6-(1-hydroxyethyl)-1-azabicyclo[3.2.0]heptane-3,7-dione-2-carboxylate (30 mg) is dissolved in dioxane (2 ml). The solution is treated with ethanol (0.5 ml), H2O (0.5 ml), NaHCO3 (8.5 mg) and 10% Pd/C (20 mg) and the resulting mixture is hydrogenated at 40 psi for 1 hr. The mixture is filtered to remove the catalyst which is washed with H2O (2.5 ml). The combined filtrate is extracted with ethyl acetate (3×2 ml), concentrated in vacuo, and lyophilized to provide sodium 6-(1-hydroxyethyl)-1-azabicyclo[3.2.0]heptane-3,7-dione-2-carboxylate.

Workup

  1. filtrationThe mixture is filtered
  2. customto remove the catalyst which
  3. washis washed with H2O (2.5 ml)
  4. extractionThe combined filtrate is extracted with ethyl acetate (3×2 ml)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dc32c323a85246d2927bd346fce252d3
Source dataset
uspto-grants-1982_03
Patent number
US04318912

Reaction notes

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