Hydrochloric Acid → HCID 10114552, compound

Participants

Reaction Steps

110 mg (1.3 mmol) of sodium hydrogen carbonate are added to 350 mg (6.7 mmol) of 4-{[4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]methylcarbamoyl}phenyl acetate (obtained in Example 56) in 5 ml of tetrahydrofuran and 500 μl of water. The reaction medium is stirred at room temperature for 48 hours and then diluted in ethylacetate and acidified to pH 3-4 with 1N hydrochloric acid solution. The organic phase is separated out after settling of the phases has taken place, dried over sodium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a 99/1 dichloromethane/methanol mixture. After evaporation of the solvents, 250 mg (83%) of N-[4′(2,4-dioxothiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-4-hydroxy-N-methylbenzamide are collected in the form of a white powder with a melting point of 110° C.

Provenance & Evidence