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

HRID 1269675Notes

Reaction equation

HRID 1269675 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:22][C:23]1[CH:35]=[CH:34][C:26]([O:27][CH2:28][C:29]([O:31]CC)=[O:30])=[C:25]([CH3:36])[CH:24]=1)[C:6]1[CH:7]=[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+]>CO.O1CCCC1>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:22][C:23]1[CH:35]=[CH:34][C:26]([O:27][CH2:28][C:29]([OH:31])=[O:30])=[C:25]([CH3:36])[CH:24]=1)[C:6]1[CH:7]=[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 58622889Ethyl [4-({(2-methoxyethyl)[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)-2-methylphenoxy]acetate

Product 1

HCID 18448289[4-({(2-Methoxyethyl)[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)-2-methylphenoxy]acetic acidYield 32.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl [4-({(2-methoxyethyl)[4′-(trifluoromethyl)-1,1′-biphenyl-3-yl]amino}methyl)-2-methylphenoxy]acetate (90 mg, 0.18 mmol) in methanol (2 mL) and tetrahydrofuran (2 mL), was added 2M NaOH aq. (1 mL). After stirring for 1 h at room temperature the solvent was removed in vacuo and the residue diluted with water (10 mL) acidified with 2M HCl, before extraction into ethyl acetate (2×20 mL). The organic solution was dried (MgSO4) and the solvents removed in vacuo to afford the title compound as a white solid (28 mg).

Workup

  1. customwas removed in vacuo
  2. additionthe residue diluted with water (10 mL)
  3. extractionacidified with 2M HCl, before extraction into ethyl acetate (2×20 mL)
  4. dry with materialThe organic solution was dried (MgSO4)
  5. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-d13a957585e54960b8b67ca0296bf370
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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