1-Methylimidazole → 4-(1-(Bis(4-methoxyphenyl)(phenyl)methoxy)icosan-3-yloxy)-4-oxobutanoic acid triethylamine salt

HRID 2407053Notes

Reaction equation

HRID 2407053 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:38]2[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=2)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:10][CH2:11][CH2:12][CH:13]([OH:31])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:5][CH:4]=1.[C:46]1(=[O:52])[O:51][C:49](=[O:50])[CH2:48][CH2:47]1.[CH2:53]([N:55]([CH2:58][CH3:59])[CH2:56][CH3:57])[CH3:54].CN1C=CN=C1>C(Cl)Cl>[CH2:53]([N:55]([CH2:58][CH3:59])[CH2:56][CH3:57])[CH3:54].[CH3:45][O:44][C:41]1[CH:40]=[CH:39][C:38]([C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:10][CH2:11][CH2:12][CH:13]([O:31][C:46](=[O:52])[CH2:47][CH2:48][C:49]([OH:51])=[O:50])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:43][CH:42]=1

Participants

6

Reactant 4

HCID 13901-MethylimidazoleHCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 687487641-(Bis(4-methoxyphenyl)(phenyl)methoxy)icosan-3-ol

Product 1

HCID 687468894-(1-(Bis(4-methoxyphenyl)(phenyl)methoxy)icosan-3-yloxy)-4-oxobutanoic acid triethylamine salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-(bis(4-methoxyphenyl)(phenyl)methoxy)icosan-3-ol (6.8 g, 11.0 mmoles), succinic anhydride (1.1 g, 11.0 mmoles), triethylamine (4.6 mL, 33.0 mmoles) and 1-methylimidazole (0.44 mL, 5.5 mmoles) are dissolved in methylene chloride (68 mL). The reaction is stirred at ambient temperature for five days, during which time the solution darkened. The solution is then diluted with methylene chloride (100 mL) and washed twice with ice-cold aqueous citric acid (10% [w/v], 50 mL) and once with saturated aqueous sodium chloride (50 mL). The methylene chloride solution is dried over anhydrous sodium sulfate, filtered and evaporated to a dark resin. The crude product is purified on silica gel (200 mL bed volume) eluting with methylene chloride:triethylamine (95:5 [v/v/v], 500 mL), then methylene chloride:methanol:triethylamine (93:2:5 [v/v/v], 1000 mL). Fractions containing pure product by thin layer chromatography are pooled and evaporated to a resin. The resin is dried well in vacuo. The yield is 2.4 g (30%).

Workup

  1. washwashed twice with ice-cold aqueous citric acid (10% [w/v], 50 mL) and once with saturated aqueous sodium chloride (50 mL)
  2. dry with materialThe methylene chloride solution is dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated to a dark resin
  5. customThe crude product is purified on silica gel (200 mL bed volume)
  6. washeluting with methylene chloride:triethylamine (95:5 [v/v/v], 500 mL)
  7. additionFractions containing pure product by thin layer chromatography
  8. customevaporated to a resin
  9. customThe resin is dried well in vacuo

Sources & evidence

ORD record
ord-3523e13c5f604b2981ae106f044bcca1
Source dataset
uspto-grants-2014_08
Patent number
US08809514B2

Reaction notes

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