phenylalanine --> PAA

[ChemicalSolution]

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

[Elementary]

Wouldn't a straight oxidisation of phenylalanine to PAA (phenylacetic acid) be easier ?
Nobodys home

[Aurelius]

How do you suggest doing that?

[Antoncho]

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

[Elementary]

Threads starting with :

Post 258083 (missing)

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

Post 248773 (missing)

(timsong: "Oxidation Of Phenylalanine", Stimulants)
Nobodys home

[Elementary]

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

Pyrolytic conversion of phenyalanine to phenylacetaldehyde

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

And an article on the Strecker-reaction

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

Don't cry for me I'm the cleaner

[Lem2]

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.
He who makes a beast of himself gets rid of the pain of being a man.