1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67087180, compound

Participants

Reaction Steps

To 1.0 g (2 mmol) of 4-[({[benzyloxycarbonyl-((S)-1-methoxycarbonyl-ethyl)-amino]-methyl}-cyano-methyl)-amino]-butyric acid tert-butyl ester in 2 ml of THF was added 0.1 g (2 mmol) of lithium hydroxide monohydrate in 0.5 ml of water. The reaction was stirred for 16 h after which time it was evaporated to dryness. The residue was redissolved in 2 ml of DMF and 0.5 g (2 mmol) of EDCI and 0.3 g (2 mmol) of HOBT was added and the mixture stirred for 2 h. The reaction was then evaporated, the residue redissolved in EtOAc, washed with water, brine, dried (Na2SO4) and concentrated to give after flash silica gel column (n-heptane/EtOAc 4:6 to 1:1) the title compound in 78% yield as a colorless gum. MS: 416.3 (MH+).

Provenance & Evidence