Sodium Hydroxide → [4-({(2-Methoxyethyl)[2-methyl-4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)-2-methylphenoxy]acetic acid

HRID 1269680Notes

Reaction equation

HRID 1269680 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:23][C:24]1[CH:36]=[CH:35][C:27]([O:28][CH2:29][C:30]([O:32]CC)=[O:31])=[C:26]([CH3:37])[CH:25]=1)[C:6]1[C:7]([CH3:22])=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[CH:9]=[CH:10][CH:11]=1.[OH-].[Na+]>C1COCC1.CO>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:23][C:24]1[CH:36]=[CH:35][C:27]([O:28][CH2:29][C:30]([OH:32])=[O:31])=[C:26]([CH3:37])[CH:25]=1)[C:6]1[C:7]([CH3:22])=[C:8]([C:12]2[CH:13]=[CH:14][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=2)[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58622893Ethyl [4-({(2-methoxyethyl)[2-methyl-4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)-2-methylphenoxy]acetate

Product 1

HCID 18448286[4-({(2-Methoxyethyl)[2-methyl-4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)-2-methylphenoxy]acetic acidYield 95.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl [4-({(2-methoxyethyl)[2-methyl-4′-(trifluoromethyl)-1,1′-biphenyl-3-yl]amino}methyl)-2-methylphenoxy]acetate (500 mg, 0.97 mmol) in THF (6 mL) and MeOH (6 mL) was added NaOH (2M; 3 mL) and the resultant solution stirred for 2 h at room temperature. The mixture was concentrated in vacuo, acidified with 2M HCl and extracted with CH2Cl2. The organic solution was dried (Na2SO4) and the solvent removed in vacuo to afford the title compound as a colourless oil (453 mg).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic solution was dried (Na2SO4)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-2f954ab5acca452bbe02d114914c7c04
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

Loading…