Just a thought, " When an alpha- amino acid is treated with an anhydride in the presence of pyridine, the carboxyl group is replaced by an acyl group and the NH2 becomes acylated. this is called the Dakin-West reaction *
R-CH-(NH2)-COOH +(R'CO)2O>.pyridine>>R-CH(NHCOR)-COR'
The mechanism involves formation of an oxazolone.** The reaction sometimes takes place on carboxylic acids even when the amino group is not present. A number of N-substituded amino acids, RCH-(NHR')COOH, give the corresponding N-alkylated products." excerp from March's 5th edition page 812.
So in our case Glycine would end up like this,
R'-CO-NH-CH2COR', , now this need some uncupling and the result , acetone and an ethyl amid , which can be reduced with the Hoffman elimination to CH3NH2, just a thought......java
REF.
* For a review, see Buchanan, G.L. Chem.Soc. Rev. 1988,17,91
** Allinger,N.L. ; Wang, G.L. : Dewhurst, B.B. ; J. Org. Chem.1974,39,1730
http://www.dmapcatalyst.com/Reaction%20Pages/dakin.htm (http://www.dmapcatalyst.com/Reaction%20Pages/dakin.htm)