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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: reeester on June 03, 2012, 07:21:10 PM

Title: Removing t-BOC from a peptide/amino acid?
Post by: reeester on June 03, 2012, 07:21:10 PM
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
Title: Re: Removing t-BOC from a peptide/amino acid?
Post by: discodermolide on June 03, 2012, 11:19:58 PM
Quote from: reeester on June 03, 2012, 07:21:10 PM
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?
Title: Re: Removing t-BOC from a peptide/amino acid?
Post by: reeester on June 04, 2012, 12:08:00 AM
I'm only supposed to use the compounds that are given, so it needs to be taken off with that H3O+.
Title: Re: Removing t-BOC from a peptide/amino acid?
Post by: discodermolide on June 04, 2012, 12:30:32 AM
Quote from: reeester on June 04, 2012, 12:08:00 AM
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.