Acetic Acid → HCID 18606079, compound

Participants

Reaction Steps

A solution of N-(1-(S)-ethoxycarbonyl-3-phenylpropyl)-L-alanyl-(S)-2-pyrrolidineacetic acid ethyl ester (87 mg; 0.21 mmol) in 1 ml of ethanol and 1 ml of 1.0N sodium hydroxide was stirred overnight at room temperature. The mixture was concentrated under reduced pressure to remove ethanol, neutralized with dilute hydrochloric acid and poured onto a 80×12 mm column of Dowex 50W×4 ion exchange resin (H+ cycle). The column was eluted with 200 ml water followed by 100 ml of 2.5% pyridine in water. Evaporation under reduced pressure of the aqueous pyridine eluate gave the product desired as a white crystalline solid (72 mg) ms M+ 362; TLC Rf 0.57-silica gel 4:1:1-n-butanol:water:acetic acid;

Provenance & Evidence