[peptideismylife]

Hey,

I would like to know something...I have an amino acid in which I have an azido group in the side chain. The amino group is protected...but I want to deprotected to get the free amino acid. I am afraid about a possible reaction between the azido group and the amino group...thinking that amino group is nucleophilic and azido group could act as a electrophil? Because this is the main doubt that I have...as far as I know N3 could play as an Nu- and E+?

[discodermolide]

Hey,

I would like to know something...I have an amino acid in which I have an azido group in the side chain. The amino group is protected...but I want to deprotected to get the free amino acid. I am afraid about a possible reaction between the azido group and the amino group...thinking that amino group is nucleophilic and azido group could act as a electrophil? Because this is the main doubt that I have...as far as I know N3 could play as an Nu- and E+?

How far away is the amino group from the azide (in terms of no. of C atoms). Think about the canonical forms of the azide group, could a ring form by attack of the NH2 on an azide nitrogen eliminating N₂?

[peptideismylife]

Thanks for your answer!

there are 5 carbons between them, so could we envision a 7 membered ring? As u said, azido group could be an electrophilic group depending its resonance form...for that reason I think that its possible a nucleophilic attack of the amino group upon the azido group...generating the 7-membered ring? is that right?

[discodermolide]

Thanks for your answer!

there are 5 carbons between them, so could we envision a 7 membered ring? As u said, azido group could be an electrophilic group depending its resonance form...for that reason I think that its possible a nucleophilic attack of the amino group upon the azido group...generating the 7-membered ring? is that right?

I may be mistaken but this would be a 7 exo-tet and should be favored, according to Baldwin