Hydrochloric Acid → 3-[4-(Benzyloxy)phenyl]-2-(5-phenyl-1H-imidazol-2-ylthio)propionic acid

HRID 970091Notes

Reaction equation

HRID 970091 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([S:21][C:22]2[NH:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:25][N:26]=2)[C:17]([O:19]C)=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Cl.O>CO.O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH:16]([S:21][C:22]2[NH:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:25][N:26]=2)[C:17]([OH:19])=[O:18])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 11539546HCID 11539546, compound

Product 1

HCID 116691643-[4-(Benzyloxy)phenyl]-2-(5-phenyl-1H-imidazol-2-ylthio)propionic acidYield 42%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

The crude product from Step A was dissolved in a MeOH/H2O mixture (2:1, 4 ml). 0.7 g KOH was then added to the solution and the mixture was refluxed for 2 h. Subsequently, the reaction mixture was neutralized with 1M HCl, a small amount of water was added and the mixture extracted with ethyl acetate. The solvent was evaporated. The product was purified by chromatography (SiO2; ethyl acetate). The yield was 42%.

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. extractionthe mixture extracted with ethyl acetate
  3. customThe solvent was evaporated
  4. customThe product was purified by chromatography (SiO2; ethyl acetate)

Sources & evidence

ORD record
ord-2abea860c3ae4f0b8e267cf5a784c69f
Source dataset
uspto-grants-2007_12
Patent number
US07309791B2

Reaction notes

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