Methane → HCID 23691704, compound

HRID 620423Notes

Reaction equation

HRID 620423 reaction equation
[OH:1][CH:2]([CH:4]1[C:10](=[O:11])[N:9]2[CH:5]1[CH2:6][C:7]([S:22][CH:23]([CH3:25])[CH3:24])=[C:8]2[C:12]([O:14]CC1C=CC=CC=1)=[O:13])[CH3:3].O.C(=O)(O)[O-].[Na+:31].C>O1CCOCC1.[Pd]>[OH:1][CH:2]([CH:4]1[C:10](=[O:11])[N:9]2[CH:5]1[CH2:6][C:7]([S:22][CH:23]([CH3:25])[CH3:24])=[C:8]2[C:12]([O-:14])=[O:13])[CH3:3].[Na+:31]

Participants

7

Reactant 4

HCID 297MethaneHCID 962WaterHCID 516892Sodium BicarbonateHCID 21246126HCID 21246126, compound

Product 1

HCID 23691704HCID 23691704, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Benzyl 6-(1-hydroxyethyl)-3-isopropylthio-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (25 mg) is dissolved in dioxane (2 ml) and the solution is treated with water (1 ml) containing sodium bicarbonate (6 mg) and 10% palladium on powdered charcoal (25 mg). The resulting mixture is hydrogenated at 40 psi for 1 hr. The catalyst is filtered off and washed with water (3 ml). The combined filtrate is extracted with ethyl acetate (3×2 ml), concentrated in vacuo, and lyophilized to afford sodium 6-(1-hydroxyethyl)-3-isopropylthio-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Workup

  1. filtrationThe catalyst is filtered off
  2. washwashed with water (3 ml)
  3. extractionThe combined filtrate is extracted with ethyl acetate (3×2 ml)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4e9fd139ee6f4f4a9fe5fe2c5b4accab
Source dataset
uspto-grants-1989_04
Patent number
US04820817

Reaction notes

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