Hi. Personally, I'd rather not start with tryptophan, rather than a derivative with halogen or OH instead of amino group (diazotation won't help as racemization will occur and you''l get mixture of D and L), but there are methods for your case.
Dear Sir. Concerning your issue about the azide addition to N-terminus of amino acid . I think the following below links may help you in your analysis:
I think that above PNAS paper may not be of immediate interest. You indeed need to do a diazotransfer. You can do this with triflic anhydride, as indicated in the previous wikimedia file, but this is an expensive reagent and it needs to be made in situ. It is easier to use the reagent as described here: Article An Updated Synthesis of the Diazo-Transfer Reagent Imidazole...