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

HRID 1269683Notes

Reaction equation

HRID 1269683 reaction equation
[CH2:1]([N:5]([C:23]1[CH:24]=[C:25]([C:29]2[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=2)[CH:26]=[CH:27][CH:28]=1)[S:6]([C:9]1[CH:21]=[CH:20][C:12]([O:13][CH2:14][C:15]([O:17]CC)=[O:16])=[C:11]([CH3:22])[CH:10]=1)(=[O:8])=[O:7])[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>CO.O1CCCC1>[CH2:1]([N:5]([C:23]1[CH:24]=[C:25]([C:29]2[CH:30]=[CH:31][C:32]([C:35]([F:38])([F:36])[F:37])=[CH:33][CH:34]=2)[CH:26]=[CH:27][CH:28]=1)[S:6]([C:9]1[CH:21]=[CH:20][C:12]([O:13][CH2:14][C:15]([OH:17])=[O:16])=[C:11]([CH3:22])[CH:10]=1)(=[O:7])=[O:8])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58622863Ethyl [4-({butyl[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}sulfonyl)-2-methylphenoxy]acetate

Product 1

HCID 18448307[4-({Butyl[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}sulfonyl)-2-methylphenoxy]acetic acidYield 90.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl [4-({butyl[4′-(trifluoromethyl)-1,1′-biphenyl-3-yl]amino}sulfonyl)-2-methylphenoxy]acetate (100 mg, 0.18 mmol) in methanol (4 mL) and tetrahydrofuran (4 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 (2×20 mL). The organic solution was dried (MgSO4) and the solvents removed in vacuo to afford the title compound as a white solid (85 mg).

Workup

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

Sources & evidence

ORD record
ord-38af0c821cca4f85a6dfbcabad54254d
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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