The Vespiary

The Hive => Novel Discourse => Topic started by: ChemicalSolution on April 25, 2002, 02:37:00 AM

Title: phenylalanine --> PAA
Post by: ChemicalSolution on April 25, 2002, 02:37:00 AM
Finally a use for this stuff?? 

phenylalanine ---> alpha-bromo-phenyl propionic acid via Sandmeyer reaction using KBr, HBr, NaNO2 @0C (dont' know if this will work on phenylalanine)

The bromo acid derivative is converted into 2-phenyl nitro ethane via US pat 4319059..  The procedure involves stirring in DMSO with Mg2+ ion.  This patent uses smaller bromo acids..   Again, not sure if this will work on THIS bromo acid..

2-phenyl nitro ethane is converted into PAA in very high yields using 1mmole nitroalkane, 3mmole NaNO2, 10mmole GAA in DMSO..

She THINKS this one is from JOC 62 234 1997 but she isn't 100% sure so don't throw a fit if she's wrong..

xoxo
Julia
Title: Straight oxidisation
Post by: Elementary on April 26, 2002, 01:00:00 AM
Wouldn't a straight oxidisation of phenylalanine to PAA (phenylacetic acid) be easier ?
Nobodys home
Title: Oxidation
Post by: Aurelius on April 26, 2002, 06:42:00 AM
How do you suggest doing that?
Title: A simpler suggestion...
Post by: Antoncho on April 26, 2002, 08:20:00 AM
Hey, Julie! ;)  (you wouldn't mind me calling you Julie, would you, please?)

... don't know for sure if it'll work, but no reason why it should.

Oxidize phenylalanine into phenylacetaldehyde w/hypoclrorite a la the proc. for tryptophane on Rh's page...

Then oxidize it to PAA or directly make P2P w/CH3I Grignar :)


Antoncho
Title: Some search engine results !
Post by: Elementary on April 26, 2002, 02:47:00 PM
Threads starting with :

Post 258083 (missing)

(Elementary: "Phenylethyl Alcohol Via  L-phenylalanine", Stimulants)

Post 248773 (missing)

(timsong: "Oxidation Of Phenylalanine", Stimulants)
Nobodys home
Title: More Info
Post by: Elementary on May 22, 2002, 10:05:00 PM
I been doing some digging around on the conversion of (L)phenylalanine to phenylacetaldehyde and come up with these bits of information :

http://beers.cz/kvas/1999/3_99/savela.htm (http://beers.cz/kvas/1999/3_99/savela.htm)



Pyrolytic conversion of phenyalanine to phenylacetaldehyde

http://www.cis.tugraz.at/ilct/MainDis.htm (http://www.cis.tugraz.at/ilct/MainDis.htm)



Ignite a small amount of L-phenylalanine in a gas: the characteristic odor of phenylacetaldehyde is perceptible.

To 5ml of a solution of L-phenylalanine(0.2-100) add 3 drops of potassium bichromate solution and heat: the characteristic odor of phenylacetaldehyde is perceptible.

http://my.ecplaza.net/miwontrading/1.asp (http://my.ecplaza.net/miwontrading/1.asp)



And an article on the Strecker-reaction

http://dfa.leb.chemie.tu-muenchen.de/EJahr2001.html (http://dfa.leb.chemie.tu-muenchen.de/EJahr2001.html)



Don't cry for me I'm the cleaner
Title: hey antoncho, if you react phenylacetaldehyde w/ ...
Post by: Lem2 on May 23, 2002, 11:09:00 PM
hey antoncho, if you react phenylacetaldehyde w/ MeAmine first to form the imine, then hit it w/ MeMgI, you get methamphetamine w/o going through p2p. :P
He who makes a beast of himself gets rid of the pain of being a man.