I am trying to cleave a tert-butyloxycarbonyl (Boc) protecting group from an aminooxy group ($\ce{-O-NH-Boc}$) with trifluoroacetic acid (TFA) in $\ce{CH2Cl2}$ but i get minimum product and too much starting material.

I need the product to be a TFA salt and not an HCl salt so I need to use TFA. Any solutions?

  • 2
    $\begingroup$ What about your reaction conditions? $\endgroup$
    – vapid
    Commented Jun 28, 2016 at 13:02

1 Answer 1


If you do a literature search (SciFinder/Reaxys), it seems that HCl in polar aprotic solvents (dioxane, THF, ether) are the 'standard' conditions for this cleavage.

You mention that you require the TFA salt, not the HCl salt, but even if you use HCl to carry out the reaction, its fairly trivial to get rid of the HCl and then convert the free amine into whatever salt you desire.

(Though as vapid said, your reaction conditions are probably quite important, and you might find if you just push the TFA reaction a little harder you can force the Boc off).


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