Potassium Acetate → HCID 54284546, compound

HRID 2081883Notes

Reaction equation

HRID 2081883 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-38b191b5352549b2a4f10042aeb7d65c
Source dataset
uspto-grants-1993_02
Patent number
US05185351

Reaction notes

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