Acetic Acid → HCID 131714196, compound

Participants

Reaction Steps

A solution of the ester product from part (e) (0.55 g., 0.64 mmole) in 95% ethanol (50 ml.) containing 10% palladium on carbon catalyst (0.2 g.) is hydrogenated under atmospheric pressure overnight. The catalyst is filtered, washed with 95% ethanol, and the filtrate and the washings are concentrated into an oily residue. This is treated for 5 minutes with 1.4N hydrochloric acid/acetic acid (10 ml.). The reaction mixture is concentrated under reduced pressure and the residue triturated with ether to yield 0.31 g. of an off-white solid residue. This crude product is purified on an HP-20 column (5% methanol/0.01N hydrochloric acid→90% methanol/0.01N hydrochloric acid) to give 0.08 g. of (3S)-1-[N-[3-(benzoylamino)-2-hydroxy-4-phenylbutyl]-L-lysyl]-L-proline, hydrochloride as a white solid; m.p. 67°-80°. Rf 0.15 (silica gel; n-butanol:acetic acid:water; 3:1:1).

Provenance & Evidence