I have been reading a lot about this particular route, and I mean a lot considering a few 27 page threads on other forums about phenylalanine. This is one of the old methods :
"An insight of the reaction of amines with trichloroisocyanuric acid"
De Luca & Giacomelli
Synlett 2004, No. 12, pp 2180
R-CH(COOH)NH2 ------> R-C#N (TCCA/H2O/NaOH/5 C)
Amino acid Nitrile time(h) Yield(%)
----------------------------------------------------------------
Ph-CH2-CH(COOH)NH2 Ph-CH2-C#N 0.4 98
HOOC-CH2-CH(COOH)NH2 HOOC-CH2-C#N 1.0 99
HOOC-CH2-CH2-CH(COOH)NH2 HOOC-CH2-CH2-C#N 0.5 90
BnOPh-CH2-CH(COOH)NH2 BnOPh-CH2-C#N 1.0 93
CH3-CH2-CH(CH3)-CH(COOH)NH2 CH3-CH2-CH(CH3)-C#N 0.5 98
The reaction can be preformed with 2/3 equivalents of TCCA directly on an aqueous solution of the alpha-aminoacid under basic conditions: after 30 minutes to 1 hour, the nitriles can be recovered quantitatively without any trace of byproducts.
It is worth mentioning to note that in the case of amino acids having multiple chiral centers such as isoleucine the reaction occurs without any racemization of the adjacent chiral center.
[...]
General One-Pot Procedure.
The reported procedure is representative: L-Phenylalanine (1.2 g, 7.6 mmol) was dissolved in an aq solution of 2 N NaOH (3.8 mL) and treated with TCCA (1.17 g, 5.1 mmol) at 25 C. After 10 min, when TLC analysis showed the complete absence of the L-phenylalanine, the reaction mixture was treated with HCl (15 mL), followed by an aq solution of 3 N HCl (2.5 mL). After 10 min the mixture was extracted twice with Et2O (15 mL). The organic layers were washed with H2O (10 mL), dried on Na2SO4, filtered and concentrated in vacuo to yield phenylacetonitrile (0.87 g, 98%)
(exerpt from the Hive)
I know that there have been quite a few advances made to this route. The thread that this came from was a bit open ended. Noone actually claimed success with this method. Lots of runaway rxns tho. That problem was actually solved. Slow addition and an ice bath. Anyone actually tried this method? If not, then someone is about to......as soon as his Kg of phenylalanine arrives.