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

HRID 1269676Notes

Reaction equation

HRID 1269676 reaction equation
[CH3:1][C:2]1[CH:14]=[C:13]([CH2:15][N:16]([CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[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][CH2:35][CH2:36][CH3:37])[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

HCID 14798Sodium HydroxideHCID 58622867Ethyl [2-methyl-4-({pentyl[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)phenoxy]acetate

Product 1

HCID 18448345[2-Methyl-4-({pentyl[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)phenoxy]acetic acidYield 110.5%

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}methyl)phenoxy]acetate (54 mg, 0.11 mmol) in MeOH (2 mL) and THF (2 mL) at room temperature was added 2M NaOH (1 mL, 2 mmol). The resultant mixture was stirred for 1 h and then the solvents were removed in vacuo. The residue was partitioned between CH2Cl2 (2×10 mL) and 2M HCl (10 mL). The organic solution was passed through a hydrophobic frit and the solvent was removed, affording the title compound as a white solid (59 mg).

Workup

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

Sources & evidence

ORD record
ord-f045e5c5ca754257b71795d315e75ba5
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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