Sodium Hydroxide → 4-[3-(Imidazol-1-yl)-2-(thiazol-2-yl)-propyl]-2-phenyl-benzoic acid

HRID 2227996Notes

Reaction equation

HRID 2227996 reaction equation
[N:1]1([CH2:6]/[C:7](/[C:25]2[S:26][CH:27]=[CH:28][N:29]=2)=[CH:8]/[C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:10]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[OH-].[Na+]>CO>[N:1]1([CH2:6][CH:7]([C:25]2[S:26][CH:27]=[CH:28][N:29]=2)[CH2:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:10]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70030731methyl 4-[(Z)-3-(imidazol-1-yl)-2-(thiazol-2-yl)-prop-1-enyl]-2-phenyl-benzoate

Product 1

HCID 184745804-[3-(Imidazol-1-yl)-2-(thiazol-2-yl)-propyl]-2-phenyl-benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Product from step B (0.39 g; 0.96 mmol) and NaOH 2N, (1.25 ml) in MeOH (8 ml) was heated at reflux for 2 hours. After evaporation of the solvent and neutralisation at pH6, the residue was purified on reverse phase silica eluting with MeOH/(NH4)2CO3 buffer (2 g/l, pH7) 20/80 to give 4-[3-(imidazol-1-yl)-2-(thiazol-2-yl)-propyl]-2-phenyl-benzoic acid.

Workup

  1. temperatureat reflux for 2 hours
  2. customAfter evaporation of the solvent and neutralisation at pH6
  3. customthe residue was purified on reverse phase silica eluting with MeOH/(NH4)2CO3 buffer (2 g/l, pH7) 20/80

Sources & evidence

ORD record
ord-5be8c18203614920a3fe21919f40318d
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

Loading…