Citric Acid → HCID 18536345, compound

HRID 412554Notes

Reaction equation

HRID 412554 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:35]=[CH:34][C:17]([O:18][CH2:19][C:20]3[N:24]([CH2:25][CH2:26][OH:27])[C:23]4[CH:28]=[CH:29][C:30]([C:32]#[N:33])=[CH:31][C:22]=4[N:21]=3)=[CH:16][CH:15]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].CI.[C:40](O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:35]=[CH:34][C:17]([O:18][CH2:19][C:20]3[N:24]([CH2:25][CH2:26][O:27][CH3:40])[C:23]4[CH:28]=[CH:29][C:30]([C:32]#[N:33])=[CH:31][C:22]=4[N:21]=3)=[CH:16][CH:15]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18536369HCID 18536369, compound

Product 1

HCID 18536345HCID 18536345, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[4-(1-tert-butoxycarbonylpyrrolidin-3-yloxy)-phenoxymethyl]-5-cyano-1-(2-hydroxyethyl)benzimidazole (270 mg) in tetrahydrofuran (5 ml) was added 60% sodium hydride (271 mg) at room temperature, and the mixture was stirred for 30 min. Thereto was added methyl iodide (0.105 ml), and the mixture was stirred for 24 hours. After completion of the reaction, 10% aqueous citric acid solution was added and the mixture was extracted with ethyl acetate and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (hexane:acetone=4:1) and dried under reduced pressure to give the title compound (199 mg).

Workup

  1. stirringthe mixture was stirred for 24 hours
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe obtained residue was purified by silica gel column chromatography (hexane:acetone=4:1)
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-860486de4d60452ba5b531d67bbcd82e
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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