Hydrochloric Acid → HCID 10140000, compound

Participants

Reaction Conditions

Reaction Steps

250 mg (0.45 mmol) of N-[6-benzyloxy-4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methyloctanamide, 4 ml of acetonitrile and 130 mg (0.65 mmol) of iodotrimethylsilane are introduced into a round-bottomed flask under a stream of nitrogen. The reaction medium is heated, at 50° C. for 3 hours. At room temperature, 450 μl of 1N hydrochloric acid and 450 μl of tetrabutylammonium fluoride are added. The medium is then diluted with ethyl acetate and washed with sodium thiosulfate solution. After separation of the phases once settling has taken place, the organic phase is dried over magnesium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with an ethyl acetate/heptane mixture (6/4). 150 mg (72%) of N-[4′-(2,4-dioxo-thiazolidin-5-ylmethyl)-6-hydroxybiphenyl-3-ylmethyl]-N-methyloctanamide are obtained in the form of a yellowish foam.

Provenance & Evidence