[reeester]

Hey all, I'm trying to work out this synthesis problem on a practice test my teacher gave me. I think I have the part where the amino acid is added to the peptide chain correct, but I'm having a hard time with the mechanism/removing t-BOC to get the final problem. Anyone have an idea on how to do this? Picture here:

http://i50.tinypic.com/xo07f4.jpg

[discodermolide]

Hey all, I'm trying to work out this synthesis problem on a practice test my teacher gave me. I think I have the part where the amino acid is added to the peptide chain correct, but I'm having a hard time with the mechanism/removing t-BOC to get the final problem. Anyone have an idea on how to do this? Picture here:

http://i50.tinypic.com/xo07f4.jpg

You use neat trifluoroacetic acid and the products are the TFA salt of the amino acid plus CO2 plus isobutylene.
Perhaps you can take it from there?

[reeester]

I'm only supposed to use the compounds that are given, so it needs to be taken off with that H3O+.

[discodermolide]

I'm only supposed to use the compounds that are given, so it needs to be taken off with that H3O+.

Substitute H₃O⁺ for TFA.