1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-Methyl-2-(4-{[5-(4-trifluoromethoxy-phenyl)-pent-4-ynoylamino]-methyl}-phenoxy)-propionic acid ethyl ester

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Reaction Conditions

Reaction Steps

0.16 g (0.68 mmol) of 2-(4-aminomethyl-phenoxy)-2-methyl-propionic acid ethyl ester [PCT Int. Appl. WO 2002/096895 A1] and 0.16 g (0.62 mmol) of 5-(4-trifluoromethoxy-phenyl)-pent-4-ynoic acid (example 29D]) were dissolved in 4 ml of dichloromethane. This solution was cooled to 0° C. and then 0.14 g (0.74 mmol) of N-(3-dimethylamino-propyl)-N′-ethyl-carbodiimide-hydrochloride was added and the reaction stirred for 28 hours at ambient temperature. It was subsequently poured into aqueous 10% KHSO4/ether and extracted two fold with ether; the organic layers were washed with aqueous saturated NaHCO3, dried (Na2SO4), filtered and evaporated. The crude product was purified by flash chromatography (SiO2; n-heptane/AcOEt=9:1 to 1:2) to give 0.14 g of the title compound as light brown oil.

Provenance & Evidence