Potassium Hydroxide → (3-cyclopropyl-2-oxo-4-phenyl-2,3-dihydro-1H-imidazol-1-yl)-acetic acid

HRID 660874Notes

Reaction equation

HRID 660874 reaction equation
C([O:3][C:4](=[O:21])[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:8]([CH:17]2[CH2:19][CH2:18]2)[C:7]1=[O:20])C.[OH-].[K+]>CO>[CH:17]1([N:8]2[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:10][N:6]([CH2:5][C:4]([OH:21])=[O:3])[C:7]2=[O:20])[CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 58012047Ethyl(3-cyclopropyl-2-oxo-4-phenyl-2,3-dihydro-1H-imidazol-1-yl)-acetate

Product 1

HCID 58011929(3-cyclopropyl-2-oxo-4-phenyl-2,3-dihydro-1H-imidazol-1-yl)-acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

350 mg (1.222 mmol) of ethyl (3-cyclopropyl-2-oxo-4-phenyl-2,3-dihydro-1H-imidazol-1-yl)-acetate from Example 123A are placed in 2 ml methanol, treated with 0.5 ml 20% aqueous potassium hydroxide and stirred for two hours at room temperature. The methanol is removed on the rotary evaporator, and the residue acidified with 2 N hydrochloric acid and extracted with dichloromethane. The organic phase is separated, dried over sodium sulphate and concentrated. It is purified by flash chromatography on silica gel (eluent: dichloromethane/methanol first 50:1, then 25:1). 166 mg (53% of theory) of the target compound are thus obtained.

Workup

  1. customThe methanol is removed on the rotary evaporator
  2. extractionextracted with dichloromethane
  3. customThe organic phase is separated
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customIt is purified by flash chromatography on silica gel (eluent
  7. custom166 mg (53% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-608f94493d8842799ce01cbdc6d1876b
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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