Romanosow
Harmless
Posts: 6
Registered: 14-10-2014
Member Is Offline
Mood: No Mood
|
|
How selectively remove Boc group (compound also has a phthalimide group)?
Can somebody help me? In my compound i have three phthalimide and Boc-amine groups. How i can remove the Boc group from my compound?
|
|
|
Chemosynthesis
International Hazard
Posts: 1071
Registered: 26-9-2013
Member Is Offline
Mood: No Mood
|
|
Could you please post the SMILES of your chemical in question? We can use [SMILES.] and [/SMILES.] code without the periods inside brackets. I would
suggest trying Zn/HCl.
edit
If that doesn't work, perhaps AcOH in EtOAc, though I don't get RSC pubs or know your substrate so this may not be appropriate.
J. Chem. Soc., Chem. Commun. 1979, 495-510
[Edited on 14-10-2014 by Chemosynthesis]
|
|
|
AvBaeyer
National Hazard
Posts: 651
Registered: 25-2-2014
Location: CA
Member Is Offline
Mood: No Mood
|
|
The standard reagents for removing Boc groups are anhydrous trifluoroacetic acid and 4 M HCl in ethyl acetate (anhydrous), both reagents being used at
or below room temperature. The first gives the TFA salt, the second gives the HCl salt. The phthalimide should be stable to both reagents. Check out
one of the protecting group books widely available to those who look.
AvB
|
|
|
Romanosow
Harmless
Posts: 6
Registered: 14-10-2014
Member Is Offline
Mood: No Mood
|
|
Thanks! I solved my problem using TFA in dichlormethane with 5% water. 4M HCl also work, but forms some byproducts.
|
|
|
![[*]](images/xpblue/default_icon.gif){kind=icon}
