ORGLIST: maleimide troubles-more details

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From: Witek Mozga (mozga$##$trimen.pl)
Date: Thu Sep 20 2001 - 10:59:49 EDT



Hi,

Thanks for all the responses. I have to precise my question a little.

I am not trying to acylate the maleimide itself. It is just present in the
structure. The nitrogen of maleimide is substituted with an alkyl
group. The alkyl group has a secondary amino group in the side chain
and I am trying to acylate this amino group. This amine was BOC
protected. I removed BOC using HCl/AcOEt and tried to acylated the
obtained hydrochloride in anhydrous conditions with benzoyl
chloride/ Et3N but it failed. I obtained a small drop of tar that revealed
a forest of peaks on HPLC. Then I tried to utilize TsOH instead of HCl.
Boc was succesfuly cleaved but the acylation process failed again.
(many peaks on HPLC). I tried then to free the unprotected amine from
its salt prior to acylation but it failed also. Any ideas??

The reaction seems simple and I am confused very much about its
behaviour. There are no other groups in the structure but the amine I
intend to acylate and the maleimide.


Witek
http://www.trimen.pl/witek/
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