ORGLIST: aminolysis of esther to amide in aminoacid serie

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From: Marino Tadeu Fabi (mtadeu$##$mpc.com.br)
Date: Fri Oct 27 2000 - 22:42:41 EDT

CAn someone help me with a good procedure for transforming an methyester of
a substituted l-serine into a tert butyl amide of the same substituted
serine without racemizing the S center?
It's a procedure that has to be implanted in large scale!!
this is very important at this moment....
I know I can hydrolyze the ester and afterword essay to treat for instants
with tercbutylamine and oxalylchloride, or dimetilamiopiridine...etc...but
I'm afraid of racemizing!!
my first interest is the direct transformation of the ester into the
tertbutylamide....is this possible?the aminolysis reaction....!!!! how to
do with good yeld?
As it is an esther of an amino acid to be transformed into an amide of the
same amino acid is this accompanied by supplementar difficulties in
relation to other aminolysis reactions?
thank you very much
Marino Tadeu
Brazil

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