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

HRID 1269685Notes

Reaction equation

HRID 1269685 reaction equation
[CH:1]1([CH2:4][CH2:5][N:6]([C:24]2[CH:25]=[C:26]([C:30]3[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=3)[CH:27]=[CH:28][CH:29]=2)[S:7]([C:10]2[CH:22]=[CH:21][C:13]([O:14][CH2:15][C:16]([O:18]CC)=[O:17])=[C:12]([CH3:23])[CH:11]=2)(=[O:9])=[O:8])[CH2:3][CH2:2]1.[OH-].[Na+]>CO.C1COCC1>[CH:1]1([CH2:4][CH2:5][N:6]([C:24]2[CH:25]=[C:26]([C:30]3[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:37])[F:38])=[CH:32][CH:31]=3)[CH:27]=[CH:28][CH:29]=2)[S:7]([C:10]2[CH:22]=[CH:21][C:13]([O:14][CH2:15][C:16]([OH:18])=[O:17])=[C:12]([CH3:23])[CH:11]=2)(=[O:9])=[O:8])[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58622892Ethyl [4-({(2-cyclopropylethyl)[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}sulfonyl)-2-methylphenoxy]acetate

Product 1

HCID 18448285[4-({(2-Cyclopropylethyl)[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}sulfonyl)-2-methylphenoxy]acetic acidYield 43.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl [4-({(2-cyclopropylethyl)[4′-(trifluoromethyl)-1,1′-biphenyl-3-yl]amino}sulfonyl)-2-methylphenoxy]acetate (156 mg, 0.28 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 2 h. The solvents were removed in vacuo and the residue was partitioned between EtOAc (2×20 mL) and 2M HCl (20 mL). The organic solution was dried (MgSO4) and the solvent was removed in vacuo. Purification by SPE (5 g aminopropyl cartridge), loading crude material in CH2Cl2 and then washing with MeOH, prior to eluting with 5% NH3 in MeOH. The 5% NH3 in MeOH extract was concentrated in vacuo and the residue was partitioned between CH2Cl2 (20 mL) and 2M HCl (2 mL). The organic solution was dried (MgSO4) and the solvent was removed in vacuo affording the title compound as a white solid (64.4 mg).

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue was partitioned between EtOAc (2×20 mL) and 2M HCl (20 mL)
  3. dry with materialThe organic solution was dried (MgSO4)
  4. customthe solvent was removed in vacuo
  5. customPurification by SPE (5 g aminopropyl cartridge)
  6. washwashing with MeOH
  7. washto eluting with 5% NH3 in MeOH
  8. extractionThe 5% NH3 in MeOH extract
  9. concentrationwas concentrated in vacuo
  10. customthe residue was partitioned between CH2Cl2 (20 mL) and 2M HCl (2 mL)
  11. dry with materialThe organic solution was dried (MgSO4)
  12. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-66115209ce2b47649b1d4924c75e8fb7
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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