From: will jones (willjones46$##$hotmail.com)
Date: Sat Jun 24 2006 - 14:17:36 EDT
Your product will react again with the bromo compound as the secondary amine
is more nucleophilic than the primary.
I would use reductive amination using an aldehyde instead of a halogen. 1.2
-NH2: 1.0 -C(O)- and reduce with slight excess Na(OAc)3BH.
Will
>From: "shrent" <shrent$##$rediffmail.com>
>Reply-To: shrent <shrent$##$rediffmail.com>
>To: everybody$##$orglist.net
>Subject: ORGLIST: Condensation
>Date: 24 Jun 2006 13:29:36 -0000
>
>Hi !
>
>I'm doing one condensation reaction between alanine-t-butyl/benzyl ester &
>an alpha-bromoester as under :
>
>
>PhCH2CH2CH(Br)COOC2H5 + CH3CH(NH2)COOR
>
>to
>
>PhCH2CH2(COOC2H5)CHNHCH(CH3)COOR
>
>
>where, R=Benzyl/t-butyl.
>
>i.e. eliminating HBr in this reaction.
>
>
>But unfortunately, I have just one reference route for this using
>acetonitrile as solvent & adding TEA & both of the reactants, all in
>eq.molar prop. & reflux for over 2 days.....But still not getting good
>conversion & desired purity of final compound.....
>
>Can I pls get any other route for such condensation ?
>
>Awaiting your reply !
>
>
>
>
>Warm regards,
>
>shrent
>Baroda, India.
>
>
>
>
>
>
>
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