1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → BOC-Leu-Gly-OBzl

Participants

Reaction Conditions

Reaction Steps

A solution of WSC (34 g.) in dichloromethane (50 ml.) was added dropwise to a suspension of BOC-Leu-OH (46.2 g.), HOBT (1 g.) and H-Gly-OBzl.TosOH (74 g.) in DMF (100 ml.) and dichloromethane (200 ml.) with stirring at -5° C. for 1 hour. After 1 hour, the solution was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo to remove dichloromethane. To the DMF layer was added water and the mixture was extracted with ethyl acetate (1 l.), and again with the same solvent (500 ml.). The ethyl acetate layer was washed with 1 N HCl, water, 5% sodium bicarbonate and water, in this order and dehydrated with sodium sulfate (anhydrous), then concentrated in vacuo to obtain oily BOC-Leu-Gly-OBzl (82 g.) Rf = 0.68.

Provenance & Evidence