Sodium Hydroxide → {4-[(Butyl{6-[4-(trifluoromethyl)phenyl]pyridin-2-yl}amino)methyl]-2-methylphenoxy}acetic acid

HRID 1269673Notes

Reaction equation

HRID 1269673 reaction equation
[CH2:1]([N:5]([CH2:22][C:23]1[CH:34]=[CH:33][C:26]([O:27][CH2:28][C:29]([O:31]C)=[O:30])=[C:25]([CH3:35])[CH:24]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[N:7]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>CO.O1CCCC1>[CH2:1]([N:5]([CH2:22][C:23]1[CH:34]=[CH:33][C:26]([O:27][CH2:28][C:29]([OH:31])=[O:30])=[C:25]([CH3:35])[CH:24]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:13]=[CH:14][C:15]([C:18]([F:20])([F:19])[F:21])=[CH:16][CH:17]=2)[N:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58622857Methyl {4-[(butyl{6-[4-(trifluoromethyl)phenyl]pyridin-2-yl}amino)methyl]-2-methylphenoxy}acetate

Product 1

HCID 18448319{4-[(Butyl{6-[4-(trifluoromethyl)phenyl]pyridin-2-yl}amino)methyl]-2-methylphenoxy}acetic acidYield 90.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl {4-[(butyl{6-[4-(trifluoromethyl)phenyl]pyridin-2-yl}amino)methyl]-2-methylphenoxy}acetate (40 mg, 0.082 mmol) in methanol (2 mL) and tetrahydrofuran (2 mL), was added 2M NaOH aq. (2 mL). After stirring for 1 h at room temperature the solvent was removed in vacuo and the residue acidified with 2M HCl, before extraction into ethyl acetate (2×15 mL). The organic solution was dried (MgSO4) and the solvents removed in vacuo to afford the title compound as a white solid (35 mg).

Workup

  1. customwas removed in vacuo
  2. extractionthe residue acidified with 2M HCl, before extraction into ethyl acetate (2×15 mL)
  3. dry with materialThe organic solution was dried (MgSO4)
  4. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-115ab206470449e09efb483b962cd072
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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