How do I Deprotect a Boc group?
How do I Deprotect a Boc group?
Removal of the BOC in amino acids can be accomplished with strong acids such as trifluoroacetic acid in dichloromethane, or with HCl in methanol. A complication may be the tendency of the t-butyl cation intermediate to alkylate other nucleophiles; scavengers such as anisole or thioanisole may be used.
How do I uninstall TFA after BOC deprotection?
To remove traces of TFA you can use exsiccator with KOH and – optionally – some heat. If you have the salt with TFA you could dissolve your product in water add some NH3 – until you have slight alkalline conditions – and extract your product with CHCl3 or DCM, evaporate and dry over KOH.
Is BOC acid labile?
The Boc group is stable towards most nucleophiles and bases. Therefore, an orthogonal protection strategy using a base-labile protection group such as Fmoc is possible. tert-Butyl carbamates are cleaved under anhydrous acidic conditions with the production of tert-butyl cations.
How do you get rid of residual TFA?
What is the role of BOC in deprotection?
The BOC group is generally one of the most sensitive to acids, so often selective deprotection in the presence of other acid sensitive groups is possible. The use of acids or Lewis acidic reagents leads to the generation of the t-Butyl cation as an intermediate.
How can I deprotection of BOC using TFA?
TFA is mild acid for the deprotection of Boc. if you don’t want to use TFA as you mentioned. try the attached file method. You can try with Imidazole in presence of Cs 2CO 3 in Acetonitrile as solvent for Boc deprotection.
What is the BOC (tert-Butyloxycarbonyl) protecting group?
The BOC (tert-butyloxycarbonyl) protecting group, chemically a di-tert-butyl dicarbonate (Boc 2 O), is probably the most common amine protecting group in non-peptide chemistry. The reaction conditions for the amine protection are quite flexible. The process usually achieves high yields and fast conversions under relatively mild conditions.
What is the best acid to deprotonate BOC?
TFA is mild acid for the deprotection of Boc. if you don’t want to use TFA as you mentioned. try the attached file method. TFA is mild acid for the deprotection of Boc. if you don’t want to use TFA as you mentioned. try the attached file method.
https://www.youtube.com/watch?v=rDw1mZfNHVk
