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

HRID 1269684Notes

Reaction equation

HRID 1269684 reaction equation
[CH3:1][C:2]1[CH:14]=[C:13]([S:15]([N:18]([CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:19]2[CH:20]=[C:21]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)[CH:22]=[CH:23][CH:24]=2)(=[O:17])=[O:16])[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]([S:15]([N:18]([CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:19]2[CH:20]=[C:21]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:33])([F:32])[F:34])=[CH:27][CH:26]=3)[CH:22]=[CH:23][CH:24]=2)(=[O:16])=[O:17])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58622869Ethyl [2-methyl-4-({pentyl[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}sulfonyl)phenoxy]acetate

Product 1

HCID 18448278[2-Methyl-4-({pentyl[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}sulfonyl)phenoxy]acetic acidYield 107.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl [2-methyl-4-({pentyl[4′-(trifluoromethyl)-1,1′-biphenyl-3-yl]amino}sulfonyl)phenoxy]acetate (76 mg, 0.13 mmol) in MeOH (2 mL) and THF (2 mL) at room temperature was added 2M NaOH aq. (1 mL, 2 mmol). The resultant mixture was stirred for 1 h. The solvents were removed in vacuo and the residue was partitioned between CH2Cl2 (2×15 mL) and 2M HCl (10 mL). The organic solution was passed through a hydrophobic frit and the solvent was removed in vacuo affording the title compound as a white solid (75 mg).

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue was partitioned between CH2Cl2 (2×15 mL) and 2M HCl (10 mL)
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c93a20454fa6441099483d560e98a739
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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