Hydrochloric Acid → HCID 12893584, compound

Participants

Reaction Steps

2.5 g of 3-[3-mercapto-2(S)-methylpropionyl]-4(R)-thiazolidinecarboxylic acid and 2 g of sodium hydrogen carbonate are added to 150 ml of water whereupon 2.5 g of 4-chloro-3-sulfamoylbenzoyl chloride is added slowly under ice-cooling and stirring, and the resulting mixture is stirred at room temperature for 3 hours. The reaction mixture is then made acidic with dilute hydrochloric acid under ice-cooling, and the non-crystalline solid is extracted with ethyl acetate. The extract is washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The non-crystalline solid thus obtained is purified by column chromatography on silica gel with ethyl acetate-hexane (4:1) eluants. Thusis obtained 3-[3-(4-chloro-3-sulfamoylbenzoylthio)-2(S)-methylpropionyl]-4(R)-thiazolidinecarboxylic acid as white non-crystalline powder, [α]D25 -118.8 (methanol). The dicylohexylamine salt of this product has a meltingof 173°-176° C.

Provenance & Evidence