Potassium Hydroxide → HCID 178448927, compound

Participants

Reaction Steps

A solution of 8.8 g (22.7 mmol) of 3-methoxycarbonylpropanoic acid N-butyl-N-(2'-cyanobiphenyl-4-ylmethyl)-amide and 9.8 g (29.5 mmol) of tributyltin azide in 100 ml of o-xylene is heated under reflux for 20 hours. The reaction mixture is then cooled to 20° and 100 ml of 1N potassium hydroxide solution are added thereto. The reaction mixture is stirred thoroughly for 2 hours, and the aqueous phase is separated and acidified with 2N hydrochloric acid. The resin which separates is extracted with ethyl acetate. The crude product, obtained by concentration of the ethyl acetate phase by evaporation, is flash-chromatographed on 500 g of silica gel [toluene/isopropanol/glacial acetic acid (170:30:2)] to yield 3-carboxypropanoic acid N-butyl-N-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-amide in the form of a light-brown foam that has an Rf value of 0.20 [toluene/isopropanol/glacial acetic acid (170:30:2)]. ##STR8##

Provenance & Evidence