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

HRID 1269682Notes

Reaction equation

HRID 1269682 reaction equation
[CH3:1][C:2]1[CH:14]=[C:13]([CH2:15][N:16]([S:33]([CH2:36][CH2:37][CH3:38])(=[O:35])=[O:34])[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]([S:33]([CH2:36][CH2:37][CH3:38])(=[O:34])=[O:35])[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 58622879Ethyl [2-methyl-4-({(propylsulfonyl)[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)phenoxy]acetate

Product 1

HCID 18448282[2-Methyl-4-({(propylsulfonyl)[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)phenoxy]acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl [2-methyl-4-({(propylsulfonyl)[4′-(trifluoromethyl)-1,1′-biphenyl-3-yl]amino}methyl)phenoxy]acetate (20 mg, 0.036 mmol) in MeOH (1 mL) and THF (1 mL) at room temperature was added 2M NaOH (0.5 mL, 1 mmol). The resultant mixture was stirred for 2 h. The solvents were removed in vacuo and the residue was partitioned between CH2Cl2 (2×10 mL) and 2M HCl (10 mL). The organic solution was passed though a hydrophobic frit and the solvent was removed in vacuo. Purification by autoprep. HPLC conducted on a Supelco ABZ+ column (5 μm, 10 cm×21.2 mm ID), eluting at a flow rate of 8 mL/min with a gradient of 50–95% B over 20 mins and held at 95% B for 10 mins. Where solvent A=0.1% HCO2H in H2O and solvent B=0.05% HCO2H in MeCN. The title compound was afforded as a yellow oil (10.7 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 in vacuo
  4. customPurification by autoprep
  5. washeluting at a flow rate of 8 mL/min with a gradient of 50–95% B over 20 mins

Sources & evidence

ORD record
ord-bc032e4388f646be854f82c6da8dfd57
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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