[IONIC STRENGTH]

Hey, I have a compound that stays in the aqueous layer when I try to extract it from the reaction mixture (ethyl acetate or CHCl3-IPA 3:1); the reaction takes place in Na2HPO4/NaOH buffer. I´ve tried to precipitate it from water using acetic acid but although I have got rid of a large amount of salts, it still contains them and also a part of the compound remains in the solution..I wonder if some kind of resin (ionic exchange) could help...Any suggestion?
Oh, it has a carboxylic group and an hemiacetal group; MW around 300 Da..

[discodermolide]

Hey, I have a compound that stays in the aqueous layer when I try to extract it from the reaction mixture (ethyl acetate or CHCl3-IPA 3:1); the reaction takes place in Na2HPO4/NaOH buffer. I´ve tried to precipitate it from water using acetic acid but although I have got rid of a large amount of salts, it still contains them and also a part of the compound remains in the solution..I wonder if some kind of resin (ionic exchange) could help...Any suggestion?
Oh, it has a carboxylic group and an hemiacetal group; MW around 300 Da..

Perhaps you should take the pH lower, acetic acid may not be enough to re-protonate your acid?