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Topic: Amino acid syntheses - feasible?  (Read 3450 times)

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Offline combatwombat

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Amino acid syntheses - feasible?
« on: April 21, 2009, 05:01:50 PM »
Will these routes work to produce the following amino acids from the given reagents?

They will produce racemic mixtures of D & L forms, correct?




Offline combatwombat

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Re: Amino acid syntheses - feasible?
« Reply #1 on: April 22, 2009, 06:46:23 PM »
*Ignore me, I am impatient*

can I at least get a thumbs up/thumbs down on either route?

Offline Squirmy

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Re: Amino acid syntheses - feasible?
« Reply #2 on: April 22, 2009, 07:50:39 PM »
The first one looks feasible...you might look up the Strecker synthesis as an alternative.

I have no idea what you're trying to do in the second one and there's a pentavalent carbon. Can you walk me through your line of thinking? (not about the pentavalent carbon, but the route in general :) )

Offline combatwombat

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Re: Amino acid syntheses - feasible?
« Reply #3 on: April 23, 2009, 05:22:58 PM »
Re #1: Yes, I realize the strecker would be better for the first. However, I feel like this ought to work. Does anyone know if you can use reductive amination on a carboxylic acid? This seems to be the only potentially sticky point.

Re: #2: Wow, I did not notice the pentavalent carbon. Ironically, it was the professor who put that there, not me. Don't remember what I was thinking with that, I don't see how it could work in retrospect.

Offline AWK

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Re: Amino acid syntheses - feasible?
« Reply #4 on: April 24, 2009, 01:18:02 AM »
1 You method may be work, but is much longer and expensive
2. I cannot see any nitrogen atom on the left side
http://orgsynth.org/orgsyn/orgsyn/prepContent.asp?prep=cv5p0373

http://www.uwstout.edu/faculty/schultzf/chem-201/oldQnW/quiz4.pdf - [page 5]
AWK

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