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Natural Science Forum / Chemistry / Organic Synthesis / February 2004amine protection
Hello, I'm trying to protect the amine group in L-glutamine by using a protecting group. I've tried the CBz group, but the removal with Pd/H2 is inconvenient and often doesn't work consistently. I'd like to try another group, and have thought about the p-methoxybenzyl group. The goal is to protect the amine group so the amide substituted glutamine may be cyclized to a protected N-substituted diketo piperidine moitey. My main concern is finding an easily removed protecting group. Anyone have any thoughts? Ideal conditions: close to neutral pH, not too toxic, nasty, etc..... ------------------------------------------------------- Devin Pantess, GTA Department of Chemistry University of Louisville Louisville, KY 40292 (502)852-0937 pantess@bellsouth.net  SignaturePaul J. Franklin(moderator - sci.chem.organic.synthesis) http://organicworldwide.net/sci.chem.organic.synthesis Georgia State University <chepjf@panther.gsu.edu> Atlanta, GA Hi have you thought about TMS as protecting group? You can remove under aqueos conditions. And what about BOC? It's removed in TFA oder aq. HCl. Chris > Hello, > I'm trying to protect the amine group in L-glutamine by using a > protecting group. I've tried the CBz group, but the removal with [quoted text clipped - 5 lines] > removed protecting group. Anyone have any thoughts? Ideal > conditions: close to neutral pH, not too toxic, nasty, etc..... > ------------------------------------------------------- > Devin Pantess, GTA > Department of Chemistry > University of Louisville SignaturePaul J. Franklin(moderator - sci.chem.organic.synthesis) http://organicworldwide.net/sci.chem.organic.synthesis Georgia State University <chepjf@panther.gsu.edu> Atlanta, GA > Hello, > I'm trying to protect the amine group in L-glutamine by using a > protecting group. I've tried the CBz group, but the removal with > Pd/H2 is inconvenient and often doesn't work consistently. I'd like > to try another group, and have thought about the p-methoxybenzyl > group. The goal is to protect the amine group so the amide > substituted glutamine may be cyclized to a protected N-substituted > diketo piperidine moitey. My main concern is finding an easily > removed protecting group. Anyone have any thoughts? Ideal > conditions: close to neutral pH, not too toxic, nasty, etc..... > Devin Pantess, GTA > Department of Chemistry > University of Louisville > Louisville, KY 40292 > (502)852-0937 > pantess@bellsouth.net BOC? SignatureRon Jones Don't repeat history, see unreported near misses in chemical lab/plant at http://www.crhf.org.uk . -- Paul J. Franklin(moderator - sci.chem.organic.synthesis) http://organicworldwide.net/sci.chem.organic.synthesis Georgia State University <chepjf@panther.gsu.edu> Atlanta, GA > I'd like to try another group, and >have thought about the p-methoxybenzyl group. The goal is to protect the >amine group so the amide substituted glutamine may be cyclized to a >protected N-substituted diketo piperidine moitey. It depends how you are going to make this diketopipridine. But I would try BOC (t-butoxycarbonyl). It is easily introduced with Boc2O (t-butyl pyrrocarbonate) and cleaved with anhydrous HCl in dioxane or ethyl acetate. In such anhydrous conditions nothing unexpected should happen. The final hydrochloride usualy is crystalline. SignatureWitek http://www.trimen.pl/witek/ -- Paul J. Franklin(moderator - sci.chem.organic.synthesis) http://organicworldwide.net/sci.chem.organic.synthesis Georgia State University <chepjf@panther.gsu.edu> Atlanta, GA I'm going to use p-anisoyl chloride, it's easily removed with ceric ammonium nitrate without fancy conditions. Thanks, Devin SignaturePaul J. Franklin(moderator - sci.chem.organic.synthesis) http://organicworldwide.net/sci.chem.organic.synthesis Georgia State University <chepjf@panther.gsu.edu> Atlanta, GA just an aside - what's the stability of tboc if kept refrigerated? Kirk Babb SignaturePaul J. Franklin(moderator - sci.chem.organic.synthesis) http://organicworldwide.net/sci.chem.organic.synthesis Georgia State University <chepjf@panther.gsu.edu> Atlanta, GA |
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