Citric Acid → HCID 178440168, compound

HRID 1197590Notes

Reaction equation

HRID 1197590 reaction equation
[C:1]([C:3]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]3[NH:25][N:24]=[N:23][N:22]=3)=[CH:11][CH:10]=2)[C:6]([CH2:26][CH2:27][CH3:28])=[N:5][C:4]=1[N:29]1[CH:33]=[CH:32][CH:31]=[CH:30]1)#N.[OH-:34].[K+].Cl.C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:40]>>[CH2:26]([C:6]1[N:7]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]3[NH:25][N:24]=[N:23][N:22]=3)=[CH:13][CH:14]=2)[C:3]([C:1]([OH:40])=[O:34])=[C:4]([N:29]2[CH:30]=[CH:31][CH:32]=[CH:33]2)[N:5]=1)[CH2:27][CH3:28]

Participants

5

Reactant 4

HCID 311Citric AcidHCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 178440167HCID 178440167, compound

Product 1

HCID 178440168HCID 178440168, compound

Procedure

5-Cyano-2-propyl-4-(1H-pyrrol-1-yl)-1-[(2'-(1H-tetrazol-5-yl)biphen-4-yl)methyl]-1H-imidazole (Example 22, 2.2 g) was treated with 2N KOH (75 mL) and heated at reflux for 12 hours. The resulting solution was cooled on an ice bath and treated dropwise with concentrated aqueous HCl (8 mL) followed by dropwise addition of aqueous 10% citric acid (50 mL). The resulting precipitate was collected by filtration and then it was partitioned between ethyl acetate and 10% citric acid. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated on a rotary evaporator, keeping the temperature below 25° C. to give a foam. This foam was dissolved in ether-CH2Cl2 (1:1) and diluted to turbidity with hexanes. Evaporation of solvents as above gives the title compound as a colorless powder. MS (FAB, thioglycerol) 454 (m+1), 410 (m-CO2 +1).

Workup

  1. temperatureheated
  2. temperatureat reflux for 12 hours
  3. temperatureThe resulting solution was cooled on an ice bath
  4. filtrationThe resulting precipitate was collected by filtration
  5. customit was partitioned between ethyl acetate and 10% citric acid
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated on a rotary evaporator
  9. customthe temperature below 25° C.
  10. customto give a foam
  11. customEvaporation of solvents as

Sources & evidence

ORD record
ord-364ebcb229c1481b9a4182c7ffa1b8dc
Source dataset
uspto-grants-1994_01
Patent number
US05276048

Reaction notes

Loading…