Acetic Acid → HCID 178486612, compound

HRID 480475Notes

Reaction equation

HRID 480475 reaction equation
C(OC[N:10]1[CH:14]=[C:13]([C:15]([C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][C:24]([O:32][CH3:33])=[C:25]([O:30][CH3:31])[CH:26]=3)[CH:21]=2)([OH:19])[CH:16]([CH3:18])[CH3:17])[N:12]=[CH:11]1)C1C=CC=CC=1.C(O)(=O)C>CO.[Pd]>[CH3:31][O:30][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][C:24]=1[O:32][CH3:33])[CH:21]=[C:20]([C@@:15]([C:13]1[N:12]=[CH:11][NH:10][CH:14]=1)([OH:19])[CH:16]([CH3:18])[CH3:17])[CH:29]=[CH:28]2

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 18769095HCID 18769095, compound

Product 1

HCID 178486612HCID 178486612, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

1-(1-benzyloxymethyl-1H-imidazol-4-yl)-1-(6,7-dimethoxy-2-naphthyl)-2-methyl-1-propanol (20 g) was dissolved in warm methanol (1 L). Acetic acid (10.24 mL) and 10% Pd—C (50% wet; 20 g) were added and the mixture was stirred vigorously at 40° C. for 9 h under hydrogen atmosphere at 4 atmospheric pressure. The catalyst was filtered off and the filtrate was concentrated in vacuo. The residue was dissolved in ethyl acetate (600 mL), washed with sodium bicarbonate solution and 1M sodium bisulfite solution. The water layer was extracted with ethyl acetate. The organic layers were combined and dried over Na2SO4, concentrated in vacuo. The residue was crystallized from ethyl acetate-diisopropyl ether to give the titled compound (11.15 g) as colorless crystals.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate (600 mL)
  4. washwashed with sodium bicarbonate solution and 1M sodium bisulfite solution
  5. extractionThe water layer was extracted with ethyl acetate
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was crystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-0d0b630741d445d7a2710bc72b1c547c
Source dataset
uspto-grants-2003_11
Patent number
US06649643B1

Reaction notes

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