Lithium hydroxide, monohydrate → 5-(2-Ethyl-imidazol-1-yl)-4'-methyl-biphenyl-3-carboxylic acid

HRID 2266742

Reaction equation

HRID 2266742 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)[CH:8]=[C:9]([N:11]2[CH:15]=[CH:14][N:13]=[C:12]2[CH2:16][CH3:17])[CH:10]=1)=[O:4].O[Li].O>C1COCC1.O>[CH2:16]([C:12]1[N:11]([C:9]2[CH:10]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=[C:7]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)[CH:8]=2)[CH:15]=[CH:14][N:13]=1)[CH3:17]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 577497845-(2-Ethyl-imidazol-1-yl)-4'-methyl-biphenyl-3-carboxylic acid methyl ester

Product 1

HCID 577497835-(2-Ethyl-imidazol-1-yl)-4'-methyl-biphenyl-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-(2-Ethyl-imidazol-1-yl)-4′-methyl-biphenyl-3-carboxylic acid methyl ester (750 mg) was dissolved in THF (14 mL) and water (8 mL), and LiOH hydrate (128 mg, 3.1 mmol) was added as one portion. The reaction mixture was stirred at room temperature for 3 hours, then THF was removed under reduced pressure. Concentrated HCl was added into the remaining aqueous solution to adjust the pH to ˜6. The solution was extracted with EtOAc, and the combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give 5-(2-ethyl-imidazol-1-yl)-4′-methyl-biphenyl-3-carboxylic acid

Workup

  1. customTHF was removed under reduced pressure
  2. additionConcentrated HCl was added into the remaining aqueous solution
  3. extractionThe solution was extracted with EtOAc
  4. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1f278d4a0d234f839d9ded73a6540a0a
Source dataset
uspto-grants-2010_12
Patent number
US07858654B2

Linked notes

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