N Nishi, S Tokura and J Noguchi, Bull Chem Soc Japan 43, 2900-2907 (1970)
This work is in English and from memory worked well for me in the late 70's
with BOC- and CBZ-Args provided the nitrophenylisocyanate was good stuff
and the HMPA had been freshly distilled ie that same morning!
Dave Harding
At 01:25 7/24/1998 +0400, Rodionov wrote:
>Dear Jane and Leo,
>
>As far as I know the problems with coupling to p-nitroaniline are even more
>serious than you expect: no reaction is observed when standard coupling
>procedures are employed.
>In my opinion even HATU may fail with this amine. DMAP catalysis may be
>more helpful in this case.
>
>However, an old but efficient synthetic approach for p-nitoanilides exists.
>The procedure is based on reaction of p-nitrophenylisocyanate with
>COOH-group of protected peptide or amino acid followed by carbon dioxide
>elimination.
>I have no exact reference for the related original paper at hand but I am
>sure that this old peptide chemistry (including detailed protocols) is well
>documented in:
>
>Synthese von Peptiden. (Muller, E. Ed.) In: Houben Weil's Methoden der
>Organichen Chemie, Stuttgart: Thieme 1974, Bd.15, Teil 1-2.
>
>A native German-speaking friend may be of tremendous help in getting
>necessary information from this great book!
>
>Best wishes,
> Igor Rodionov
>
>Laboratory Of Peptide Chemistry
>Branch of Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry
>Pushchino, Moscow Region
>142292, Russian Federation
>E-mail: <rodionov@fibkh.serpukhov.su> or <Igor_Rodionov@iname.com>
>Fax: (0967)-79-05-27
>Phones: (0967) 73 54 42; private: (0967) 73 58 26
>
>
>
>
>
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David RK Harding
Centre for Separation Science
Institute of Fundamental Sciences
Massey University
Palmerston North
New Zealand
phone 64 6 350-5016 (work) 64 6 356-2837 (home)
fax 64 6 354-2140 (work)