Methanol → HCID 86757908, compound

Participants

Reaction Steps

3-{4-[-(tert-Butoxycarbonylaminophenyl)ethoxy]phenyl}-(S)-2-ethoxypropanoic acid ethyl ester (27 g; 0.06 mmole) was dissolved in TBF (250 ml), and water (250 ml) was added during followed by addition of lithium hydroxide hydrate (3.75 g; 0.089 mmole) dissolved in a small amount of water. The reaction mixture was stirred at room temperature overnight and then concentrated by evaporation The residue was washed once with ethyl acetate. The water phase was acidified upon cooling with hydrochloric acid (2M) and extracted with ethyl acetate. The organic phase was washed with brine dried with magnesium sulfate and evaporated. The residue was redissolved in dichloromethane and chromatography on silica using a gradient system of dichloromethane: methanol (0-100%) gave 21.3 g (83% yield) 3-{4-[2-(4-tert-butoxycarbonylamiinophenyl)ethoxy]phenyl}-(S)-2-ethoxypropanoic acid.

Provenance & Evidence