Citric Acid → HCID 178441785, compound

HRID 1197586Notes

Reaction equation

HRID 1197586 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]3[NH:34][N:33]=[N:32][N:31]=3)=[CH:20][CH:19]=2)[C:7]([C:15]#N)=[C:8]([N:10]2[CH:14]=[CH:13][CH:12]=[CH:11]2)[N:9]=1)[CH2:2][CH2:3][CH3:4].[OH-:35].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:40]>>[CH2:1]([C:5]1[N:6]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]3[NH:34][N:33]=[N:32][N:31]=3)=[CH:20][CH:19]=2)[C:7]([C:15]([OH:40])=[O:35])=[C:8]([N:10]2[CH:14]=[CH:13][CH:12]=[CH:11]2)[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 1784417822-butyl-5-pyrrol-1-yl-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-carbonitrile

Product 1

HCID 178441785HCID 178441785, compound

Procedure

A mixture of 2-butyl-5-cyano-4-(1H-pyrrol-1-yl)-1-[(2'-(1H-tetrazol-5-yl)biphen-4-yl)methyl]-1H-imidazole (Example 15, 1.4 g) and 2 N NaOH (75 mL) was heated at reflux for 24 hours. The cooled solution was acidified to pH 3.5 by portionwise addition of citric acid. The resulting precipitate was collected by filtration and rinsed well with water. The solid was then purified by C18 -reversed phase chromatography eluting with acetonitrile-water (40:60). The majority of the acetonitrile was evaporated from the pure fractions at reduced pressure, keeping the temperature below 30° C. The remaining aqueous portion was washed with ethyl acetate and the organic layer was dried over anhydrous magnesium sulfate and evaporated. The residue was dissolved in ether and evaporated once again to give the title compound as a colorless powder. MS (FAB, thioglycerol) 468 (m+1), 424 (m-CO2 +1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. filtrationThe resulting precipitate was collected by filtration
  4. washrinsed well with water
  5. customThe solid was then purified by C18 -reversed phase chromatography
  6. washeluting with acetonitrile-water (40:60)
  7. customThe majority of the acetonitrile was evaporated from the pure fractions at reduced pressure
  8. customthe temperature below 30° C
  9. washThe remaining aqueous portion was washed with ethyl acetate
  10. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  11. customevaporated
  12. dissolutionThe residue was dissolved in ether
  13. customevaporated once again

Sources & evidence

ORD record
ord-66c25a0f3772476b936da8d695aa83c8
Source dataset
uspto-grants-1994_01
Patent number
US05276048

Reaction notes

Loading…