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

HRID 1269677Notes

Reaction equation

HRID 1269677 reaction equation
[CH:1]1([CH2:4][CH2:5][N:6]([CH2:23][C:24]2[CH:36]=[CH:35][C:27]([O:28][CH2:29][C:30]([O:32]CC)=[O:31])=[C:26]([CH3:37])[CH:25]=2)[C:7]2[CH:8]=[C:9]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[CH:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>CO.C1COCC1>[CH:1]1([CH2:4][CH2:5][N:6]([CH2:23][C:24]2[CH:36]=[CH:35][C:27]([O:28][CH2:29][C:30]([OH:32])=[O:31])=[C:26]([CH3:37])[CH:25]=2)[C:7]2[CH:8]=[C:9]([C:13]3[CH:14]=[CH:15][C:16]([C:19]([F:21])([F:22])[F:20])=[CH:17][CH:18]=3)[CH:10]=[CH:11][CH:12]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58622882Ethyl [4-({(2-cyclopropylethyl)[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)-2-methylphenoxy]acetate

Product 1

HCID 18448360[4-({(2-Cyclopropylethyl)[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)-2-methylphenoxy]acetic acidYield 84.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl [4-({(2-cyclopropylethyl)[4′-(trifluoromethyl)-1,1′-biphenyl-3-yl]amino}methyl)-2-methylphenoxy]acetate (141 mg, 0.28 mmol) in MeOH (2 mL) and THF (2 mL) at room temperature was added 2M NaOH (1 mL, 2 mmol). The resultant mixture was stirred for 1.5 h, then the solvents were removed in vacuo. The residue was partitioned between CH2Cl2 (2×20 mL) and 2M HCl (20 mL). The organic solution was passed through a hydrophobic frit and the solvent was removed, affording the title compound as a white solid (115 mg).

Workup

  1. customthe solvents were removed in vacuo
  2. customThe residue was partitioned between CH2Cl2 (2×20 mL) and 2M HCl (20 mL)
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-2e29b976646e4266b4f43d2830cfc0ab
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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