Phenylacetyl chloride → N-[4'-(2,4-dioxothiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methyl-2-phenylacetamide

Participants

Reaction Steps

500 mg (1.1 mmol) of 5-(3′-methylaminomethyl-biphenyl-4-ylmethyl)thiazolidine-2,4-dione trifluoroacetate, 2 ml of tetrahydrofuran and 500 μl (3.3 mmol) of triethylamine are introduced into a round-bottomed flask under a stream of nitrogen. 230 μl of phenylacetyl chloride are added dropwise and the mixture is stirred at room temperature for one hour. The reaction medium is poured into water and extracted with ethyl acetate, and the organic phase is separated out after settling of the phases has taken place, washed with water, dried over magnesium sulfate and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of dichloromethane and methanol (97/3). 360 mg(72%) of N-[4′-(2,4-dioxothiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methyl-2-phenylacetamide are obtained in the form of a white solid with a melting point of 73° C.

Provenance & Evidence