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Author: Subject: 3-amino-3-phenylpropionamide
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[*] posted on 21-8-2014 at 09:49
3-amino-3-phenylpropionamide


Is there an easy, facile synthesis for this simple compound? Perhaps starting with tyrosine?



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[*] posted on 21-8-2014 at 11:23


Brominate acetophenone and react with cyanide, to get most of the way there...
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[*] posted on 21-8-2014 at 18:20


The d,l-acid is available commercially (CAS 614-19-7) and there are likely several referenced syntheses since beta-amino acids have attracted a lot of attention. With the acid in hand, it can be converted to the amide using standard methods.

Perhaps reaction of easily available ethyl cinnamate with ammonia could give you some of the compound in one fell swoop.

The attached file, though not for the specific compound, may be of interest.

AvB

Attachment: Amine addition to electron difficient alkenes.pdf (1.3MB)
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[*] posted on 22-8-2014 at 07:51


Thank you all for the replies.



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22-9-2014 at 07:46
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[*] posted on 25-9-2014 at 19:06


From available and inexpensive cinnamic acid, one could perform an acid addition across the alkene (HBr should proceed at rt. to 60), giving the exclusive Markovnikov product (the beta halo acid in this instance due to aromatic stabilization). Aminate this, then convert the acid to amide.

Just so you know... if you are trying to make an opioid of this, I looked over all the relevant binding data, and it doesn't look promising from this route if you couldn't get there on your own. Edit: that is the only reason I bother to help you considering what how insufferable you were last time, and yet you still aren't posting in the correct sub forums without moderator assistance.


[Edited on 26-9-2014 by Chemosynthesis]
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