Sodium Hydroxide → 2-(4-Fluorophenethyl)-5-[1-(thiazol-2-yl)-2-(1-methylimidazol-5-yl)ethoxymethyl]benzoic acid

HRID 1251934Notes

Reaction equation

HRID 1251934 reaction equation
[F:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][CH2:7][C:8]2[CH:17]=[CH:16][C:15]([CH:18]([O:24][CH2:25][CH2:26][C:27]3[N:31]([CH3:32])[CH:30]=[N:29][CH:28]=3)[C:19]3[S:20][CH:21]=[CH:22][N:23]=3)=[CH:14][C:9]=2[C:10]([O:12]C)=[O:11])=[CH:4][CH:3]=1.[OH-].[Na+]>CO.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][C:8]2[CH:17]=[CH:16][C:15]([CH:18]([O:24][CH2:25][CH2:26][C:27]3[N:31]([CH3:32])[CH:30]=[N:29][CH:28]=3)[C:19]3[S:20][CH:21]=[CH:22][N:23]=3)=[CH:14][C:9]=2[C:10]([OH:12])=[O:11])=[CH:33][CH:34]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18324433Methyl 2-(4-fluorophenethyl)-5-[1-(thiazol-2-yl)-2-(1-methylimidazol-5-yl)ethoxymethyl]benzoate

Product 1

HCID 183243962-(4-Fluorophenethyl)-5-[1-(thiazol-2-yl)-2-(1-methylimidazol-5-yl)ethoxymethyl]benzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of methyl 2-(4-fluorophenethyl)-5-[1-(thiazol-2-yl)-2-(1-methylimidazol-5-yl)ethoxymethyl]benzoate (3.32 g, 6.92 mmol), sodium hydroxide (1.38 g, 34.61 mmol) in methanol (150 ml) and water (15 ml) was stirred under a nitrogen atmosphere at reflux for 18 hours, cooled to ambient temperature and the methanol evaporated off. The residue was treated with aqueous citric acid (1M, 40 ml) and extracted with dichloromethane. The organic extracts were dried and evaporated to dryness to give 2-(4-fluorophenethyl)-5-[1-(thiazol-2-yl)-2-(1-methylimidazol-5-yl)ethoxymethyl]benzoic acid as a yellow foam (2.85, 88%).

Workup

  1. temperatureat reflux for 18 hours
  2. customthe methanol evaporated off
  3. additionThe residue was treated with aqueous citric acid (1M, 40 ml)
  4. extractionextracted with dichloromethane
  5. customThe organic extracts were dried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-a6e980b505614ce78696056961e1ecd2
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

Loading…