Sodium Hydroxide → [2-Methyl-4-({propyl[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)phenoxy]acetic acid
Reaction equation
[CH3:1][C:2]1[CH:14]=[C:13]([CH2:15][N:16]([CH2:33][CH2:34][CH3:35])[C:17]2[CH:18]=[C:19]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)[CH:20]=[CH:21][CH:22]=2)[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8]CC)=[O:7].[OH-].[Na+]>CO.C1COCC1>[CH3:1][C:2]1[CH:14]=[C:13]([CH2:15][N:16]([CH2:33][CH2:34][CH3:35])[C:17]2[CH:18]=[C:19]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:25][CH:24]=3)[CH:20]=[CH:21][CH:22]=2)[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of ethyl [2-methyl-4-({propyl[4′-(trifluoromethyl)-1,1′-biphenyl-3-yl]amino}methyl)phenoxy]acetate (88 mg, 0.18 mmol) in MeOH (2 ml) and THF (2 mL) at room temperature was added 2M NaOH (1 mL, 2 mmol). The resultant solution was stirred for 1 h, then the solvents were removed in vacuo. The residue was diluted with HCl (10 mL) and extracted with CH2Cl2 (2×10 mL), followed by EtOAc (2×10 mL). The organic solutions were dried (MgSO4) and the solvents were removed in vacuo affording the title compound as a white crystalline solid (64.1 mg).
Workup
- customthe solvents were removed in vacuo
- additionThe residue was diluted with HCl (10 mL)
- extractionextracted with CH2Cl2 (2×10 mL)
- dry with materialThe organic solutions were dried (MgSO4)
- customthe solvents were removed in vacuo
Sources & evidence
- ORD record
- ord-1ec5befe3c2e443b8f72882a3d40b350
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07199239B2
Reaction notes
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