Potassium Acetate → HCID 54284546, compound

HRID 37013Notes

Reaction equation

HRID 37013 reaction equation
C([O-])(=O)C.[K+].[CH2:6]([C:10]1[N:11]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([O:27][CH3:28])=[O:26])=[C:21]([O:29][CH2:30][O:31][CH3:32])[CH:20]=2)[C:12]([CH:16]=[O:17])=[C:13](Cl)[N:14]=1)[CH2:7][CH2:8][CH3:9]>[Pd].CO>[CH2:6]([C:10]1[N:11]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([O:27][CH3:28])=[O:26])=[C:21]([O:29][CH2:30][O:31][CH3:32])[CH:20]=2)[C:12]([CH:16]=[O:17])=[CH:13][N:14]=1)[CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 2

HCID 517044Potassium AcetateHCID 199368122-n-butyl-1-(4-carbomethoxy-3-methoxymethoxyphenyl)methyl-4-chloro-1H-imidazol-5-carboxaldehyde

Product 1

HCID 54284546HCID 54284546, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a suspension of 0.32 g of 10% palladium on carbon in 15 mL of methanol containing potassium acetate (0.813 g, 8.28 mmol) was added a solution of 2-n-butyl-1-(4-carbomethoxy-3-methoxymethoxyphenyl)methyl-4-chloro-1H-imidazol-5-carboxaldehyde (3.27 g, 8.28 mmol) in 60 mL of methanol. The reaction was hydrogenated at 4 psi for 40 minutes. The solid was filtered and the filtrate was concentrated in vacuo. The residue was partitioned between diethyl ether and water. The pH of the aqueous layer was adjusted to 7.5 with 5% sodium carbonate solution. The layers were separated and the organic layer was washed with brine and dried with magnesium sulfate. The solvent was removed in vacuo to give 2.59 g (87%) of product as an oil.

Workup

  1. filtrationThe solid was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was partitioned between diethyl ether and water
  4. customThe layers were separated
  5. washthe organic layer was washed with brine
  6. dry with materialdried with magnesium sulfate
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-51837b2c36fd4f8882642b4a4c74d738
Source dataset
uspto-grants-1995_05
Patent number
US05418250

Reaction notes

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