Acetic Acid → HCID 22993808, compound

HRID 1167636Notes

Reaction equation

HRID 1167636 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[NH:13][C:14](=[NH:19])[CH2:15][CH2:16][CH2:17][CH3:18].[CH2:20](N(CC)CC)C.[C:27]([OH:30])(=O)[CH3:28]>C(O)(C)C>[CH2:15]([C:14]1[N:13]([C:6]2[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:5]=2[O:4][CH2:3][O:2][CH3:1])[C:28]([CH:27]=[O:30])=[CH:20][N:19]=1)[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8471TriethylamineHCID 178446839HCID 178446839, compound

Product 1

HCID 22993808HCID 22993808, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of N-(2-Methoxymethoxy-4-methoxyphenyl)pentanamidine (5.10 g, 0.019 mol) in iso-propanol (50 ml) was added triethylamine (3.20 ml, 0.0230 mol), acetic acid (1.4 ml, 0.025 mol) and 2-bromo-1,3-dicarboxaldehyde propane (3.20 g, 0.0211 mol), respectively. The mixture was stirred at reflux for 5 h and then cooled to room temperature. After filtration and concentration, The crude residue was dissolved in ethyl acetate and washed with 10% sodium bicarbonate solution, water, dried (Na2SO4). After removing the solvent under reduced pressure, flash chromatography of the residue (silica gel, 25% ethyl acetate/hexane) afforded the title compound as a dark yellow oil (3.85 g, 63%).

Workup

  1. temperatureat reflux for 5 h
  2. filtrationAfter filtration and concentration
  3. dissolutionThe crude residue was dissolved in ethyl acetate
  4. washwashed with 10% sodium bicarbonate solution, water
  5. dry with materialdried (Na2SO4)
  6. customAfter removing the solvent under reduced pressure, flash chromatography of the residue (silica gel, 25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-077080e9ac6e43108413957ab2669894
Source dataset
uspto-grants-2003_09
Patent number
US06620826B2

Reaction notes

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