Hydrochloric Acid → 4-Methyl-3-[[1-oxo-2-(tricyclo[3.3.1.13,7]dec-1-yl)ethyl]amino]phenoxy-acetic acid, hydrochloride salt

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(5-Hydroxy-2-methylphenyl)-tricyclo[3.3.1.13,7]decane-1-acetamide from Example 12 (0.20 g) was added potassium carbonate (0.106 g) and ethyl bromoacetate (0.3 ml). The reaction mixture was stirred and heated at 80° C. for 24 hours. Once cooled, the reaction mixture was diluted with ethyl acetate and washed with saturated brine. The organic phase was separated, dried over magnesium sulphate (MgSO4) and evaporated under reduced pressure to leave a residue which was purified by silica gel chromatography eluting with iso-hexane/diethyl ether (1:1) to give a white solid. The solid was dissolved in dioxane (20 ml) and the solution treated with 2M sodium hydroxide solution, the reaction mixture was stirred at ambient temperature for 24 hours, acidified (2M hydrochloric acid) and extracted into ethyl acetate. The organic phase was washed with brine, dried over magnesium sulphate (MgSO4) and evaporated under reduced pressure. The residue was triturated with diethyl ether to leave the title compound as a white solid (0.070 g).

Provenance & Evidence