1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2'-isobutyl-2'-[N-(9-fluorenylmethyloxycarbonyl)-D-alanyl]-4-methylvalerohydrazide

Participants

Reaction Steps

A solution of 1.85 g of (E)-2(R)-[1(S)-(carboxy)-4-phenyl-3-butenyl]-2′-isobutyl-2′-[N-(9-fluorenylmethoxycarbonyl)-D-alanyl]-4-methylvalerohydrazide in 3 ml of dimethylformamide was treated with 0.60 g of O-(tetrahydro-2H-pyran-2(RS)-yl)hydroxylamine and 0.54 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride. The mixture was stirred overnight at room temperature and then diluted with ethyl acetate and washed with 5% aqueous citric acid, 5% aqueous sodium hydrogen carbonate and brine. The ethyl acetate layer was then dried over magnesium sulphate and evaporated. The residue was triturated with hexaneldiethyl ether (2:1) to give 1.67 g of (E)-2(R)-[1(S)-(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-2′-[N-(9-fluorenylmethoxycarbonyl)-D-alanyl]-4-methylvalerohydrazide in the form of a white solid.

Provenance & Evidence