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

Participants

Reaction Steps

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).

Provenance & Evidence