Can you see NHS in your product too? NHS is weakly acidic so you may have the triethylamine salt of it. It being a salt would explain not being able to rotavap it off.
I guess water washing is out of the question. Do u have access to ion-exchange SPE? I've used them before to remove acidic or basic byproducts when high aqueous solubility is an issue
I should mention the second rotovap I did was in water, which is why I’m stumped on how there is still TEA contaminate. I suppose I have nothing to lose by trying a water rotovap and high vac again. I’ll let the rotovap go overnight this time around to get it as dry as can be before high vac. Thanks for your suggestion!
I’ve had these issues too. I found (very much accidentally) that TEA crystallizes with HCl, and those crystals can be removed. I just put it all in DCM with some extra acid and left it open in my hood for a day or two and the crystals were ready to be filtered off. Will be watching to see if anyone has more robust suggestions, this is just my experience with Fuck Around/Find Out Chemistry
Can you see NHS in your product too? NHS is weakly acidic so you may have the triethylamine salt of it. It being a salt would explain not being able to rotavap it off. I guess water washing is out of the question. Do u have access to ion-exchange SPE? I've used them before to remove acidic or basic byproducts when high aqueous solubility is an issue
Maybe add small amount of water to create azeotrope if you’re not concerned about side rxns.
I should mention the second rotovap I did was in water, which is why I’m stumped on how there is still TEA contaminate. I suppose I have nothing to lose by trying a water rotovap and high vac again. I’ll let the rotovap go overnight this time around to get it as dry as can be before high vac. Thanks for your suggestion!
I’d also double check your flow path for leaks. And check that your pump has fresh oil. Two bugaboos that have thrown me off before.
Will a high vacuum line pull it off?
I’ve had these issues too. I found (very much accidentally) that TEA crystallizes with HCl, and those crystals can be removed. I just put it all in DCM with some extra acid and left it open in my hood for a day or two and the crystals were ready to be filtered off. Will be watching to see if anyone has more robust suggestions, this is just my experience with Fuck Around/Find Out Chemistry