Citric Acid → HCID 178440183, compound

HRID 248644Notes

Reaction equation

HRID 248644 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[N:9]=[C:10]([CH2:35][CH2:36][CH3:37])[N:11]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]4[NH:34][N:33]=[N:32][N:31]=4)=[CH:20][CH:19]=3)[C:12]=2[C:13]([O:15]C)=[O:14])[C:4]([CH3:7])=[CH:5][CH:6]=1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[CH3:1][C:2]1[N:3]([C:8]2[N:9]=[C:10]([CH2:35][CH2:36][CH3:37])[N:11]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]4[NH:31][N:32]=[N:33][N:34]=4)=[CH:20][CH:19]=3)[C:12]=2[C:13]([OH:15])=[O:14])[C:4]([CH3:7])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 178440182HCID 178440182, compound

Product 1

HCID 178440183HCID 178440183, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 4-(2,5-dimethyl-1H-pyrrol-1-yl)-2-propyl-1-[(2'-(1H-tetrazol-5-yl)biphen-4-yl)methyl]-1H-imidazole-5-carboxylate 9 (Example 70) in methanol (5 mL) containing 5 mL of 2.5N NaOH was heated under reflux for 3 hours. The reaction mixture was cooled, acidified with 10% citric acid to pH 4, and extracted with ethyl acetate. The combined organic layers were dried over anhydrous MgSO4 and the solvent removed under reduced pressure. The acid was further purified by flash chromatography on silica gel eluting with 5% methanol in ethyl acetate to furnish 0.2 g for the title compound 4-(2,5-dimethyl-1H-pyrrol-1-yl)-2-propyl-1-[(2'-(1H-tetrazol-5-yl)biphen-4-yl)methyl]-1H-imidazole-5-carboxylic acid. MS (FAB, thioglycerol) 482 (M+).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  6. customthe solvent removed under reduced pressure
  7. customThe acid was further purified by flash chromatography on silica gel eluting with 5% methanol in ethyl acetate

Sources & evidence

ORD record
ord-59d5b2221b4940c0a34da4fc95f2c480
Source dataset
uspto-grants-1993_05
Patent number
US05210211

Reaction notes

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