If you are interested in small update:
I havent solved the protection yet BUT I can use the unprotected aminobenzylamine in the coupling step and it works well. 70% HPLC purity, no trace of the O-arylated compoud. Which is great because I dont have to do some protecting group dance.
Also, the coupling with TBDPS protected aminobenzylalcohol failed - the TBDPS group got cleaved during the reaction (I think I left it too long, but since I can do it with the unprotected, it doesnt matter)