1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → N-{4-[(2,2-di-methyl-1,3-dioxolan-4-yl)-methoxycarbonyl]-(S,S)-2,4-di-benzylbutyryl}-(L)-homophenylalanine

Participants

Reaction Steps

To a solution of 0.5 g of (L)-homophenylalanine 1,2:5,6-di-O-isopropylidene-D-glucofuranos-3-yl ester, 0.51 g of 4-[(2,2-dimethyl-1,3-dioxolan-4-yl)-methoxycarbonyl]-(S,S)-2,4-dibenzylbutyric acid is added 0.23 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. The solution is stirred overnight. The solution is diluted with ethyl acetate, washed in sequence with 1N hydrochloric acid, water, saturated sodium bicarbonate, water, dried (Na2SO4), filtered and concentrated. The residue is flash chromatographed on silica gel eluting with ethyl acetate-methylene chloride (1:4) giving N-{4-[(2,2-di-methyl-1,3-dioxolan-4-yl)-methoxycarbonyl]-(S,S)-2,4-di-benzylbutyryl}-(L)-homophenylalanine 1,2:5,6-di-O-iso-propylidene-D-glucofuranos-3-yl ester melting at 48°-50°.

Provenance & Evidence