Our functional groups are tertiary-butylester, vinyl sulfone and FMOC-protecting group on nitrogen. Our goal is to remove the FMOC group and then couple with an amino acid, derivative as the N-hydroxysuccinimide ester. We plan to use diethyl amine to remove the FMOC group, which two groups have used in the presence of a vinyl sulfone.* One of the groups purified by HPLC but did not provide the column, the loading, or the solvent. The other group removed the volatiles but did not do any further purification before moving on to a coupling reaction. I have to wonder whether or not the fulvene adduct with diethyl amine will be volatile enough to remove. I don't have any experience with purifying amines over silica, but I have read that sometimes triethylamine is used in the solvent. Does anyone have any suggestions on the best way to proceed?
*there is one paper that indicated when an electron-withdrawing group is bound to the sulfur of the sulfone, that addition into the vinyl group can happen.