ORGLIST: maleimide troubles-more details

Date view Thread view Subject view Author view Attachment view

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


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.


ORGLIST - Organic Chemistry Mailing List
Website / Archive / FAQ:
List coordinator: Joao Aires de Sousa (jas$##$

Date view Thread view Subject view Author view Attachment view

This archive was generated by hypermail 2.1.4 : Fri Sep 19 2003 - 12:16:28 EDT