Butyric Acid → Ethyl [4-({butyryl[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)-2-methylphenoxy]acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl [2-methyl-4-({[4′-(trifluoromethyl)-1,1′-biphenyl-3-yl]amino}methyl)phenoxy]acetate (0.07 g, 0.16 mmol) in anhydrous CH2Cl2 (2 mL) at 0° C. under nitrogen was added butyric acid (0.016 mL, 0.17 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodimide hydrochloride (33 mg, 0.17 mmol) was then added in portions followed by triethylamine (0.022 mL, 0.16 mmol). After stirring for 15 mins at 0° C. the reaction was allowed to attain room temperature and stirred for 18 h. The reaction mixture was diluted with CH2Cl2 (20 mL) and shaken with 1 M HCl (5 mL). The organic extract was separated by hydrophobic frit and the solvent removed in vacuo. Purification by Biotage™ chromatography (Silica, 12 g) eluting 9:1 cyclohexane:EtOAc afforded the title compound as a colourless oil (40 mg).

Provenance & Evidence