Basically I took Mannose Amine and acylated it with benzoic acid using EDC ( 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide). The problem is the fact that I can not, no matter how hard I try, separate out the EDC and final product doing a column running 15% DCM:MeOH. I extracted out impurties by dissolving the product in water and extracting with ethyl acetate (the compound dissolves in water). The problem is that EDC is also water soluble. Anyone have any ideas on how to get the EDC out? Would a SPE cartidge work that would bind the EDC amine and flush through my product? That's probably the last thing I could think of in order to purify my material. I'm definitely not a rookie when it comes to running chromatography, I really don't think it is going to separate out on a flash column very easily.