I have tried to do so via the EDAC/NHS mechanism and all the resulted products are soluble in water. I cannot separate the product that I desire from the mixture.
Addition of amines with large hydrocarbon tails to acid will produce lipophilic salts ( easy extractable with CH2Cl2 or CHCl3, for instance), NBu3, HN(cyclo-Hex)2 are readily available. After extarction neutralize with NaOH to sodium salt, and extraxt amine by hydrocarbon solvent (toluene,...)
Thank you for your suggestion. I am also searching an alternative for the amide bond formation, rather than EDAC/NS.
What organic solvent is suitable for the reaction with DCC?
(DCM, DMF or THF)
I would suggest to go with DCC/DMAP, if your product is water soluble it is easy to remove the DCU, you may end up with almost pure desired product
My advice is to try DCC alone first together with DMF as a medium. DCU will form as a precipitate & thus will be easily removed.
Yes, DCC is a good carbodiimide, but the amino acid that I worked with is not soluble in DCM, DMF or THF.
Why not use a polymer supported aminoacid, do the coupling with EDAC/NHS in water or a aqueous biphasic mixture, filter the immobilized product at the end and then cleave off your product.
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