Hydrochloric Acid → (2S)-3-(4-{2-[(4-Chlorobenzyl)(ethyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoic Acid

Participants

Reaction Steps

To a solution of ethyl(2S)-3-(4-{2-[(4-chlorobenzyl)(ethyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoate (0.240 g, 0.54 mmol) in THF (30 mL) was added aqueous 0.10 M LiOH (15 mL) and the solution was stirred at room temperature overnight. After neutralisation with 5% HCl, the solvent volume was reduced in vacuo and the remaining aqueous phase was acidified with 5% HCl and extracted with methylene chloride (2×50 mL). The combined organic phase was washed with brine (50 mL), dried over Na2SO4, and concentrated in vacuo. Purification on a prepacked column of silica gel (Isolute® SPE Column, 2 g/15 mL) with ethyl acetate as the eluent afforded 0.138 g (61%) of a pale yellow oil.

Provenance & Evidence