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

HRID 1269681Notes

Reaction equation

HRID 1269681 reaction equation
[C:1]([N:6]([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:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>CO.O1CCCC1>[C:1]([N:6]([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:7]1[CH:8]=[C:9]([C:13]2[CH:14]=[CH:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=2)[CH:10]=[CH:11][CH:12]=1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58622842Ethyl [4-({butyryl[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)-2-methylphenoxy]acetate

Product 1

HCID 18448320[4-({Butyryl[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)-2 methylphenoxy]acetic acidYield 73.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl [4-({butyryl[4′-(trifluoromethyl)-1,1′-biphenyl-3-yl]amino}methyl)-2-methylphenoxy]acetate (40 mg, 0.078 mmol) in methanol (2 mL) and tetrahydrofuran (2 mL), was added 2M sodium hydroxide (1 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 (28 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-8e0b75f24d684e23ba32c84c8c5a3895
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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