ORGLIST:Amides from ESTERS and amines?

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From: samarium Steiner (neptunium$##$gmx.net)
Date: Wed Feb 19 2003 - 05:34:15 EST

Hello everybody

I'm looking for a method to form an amide directly from an ester and a
primary amine. Small esters such as methyl- and ethyl formate and methyl- and
ethylacetate can be heated with the amine affording the corresponding formamides
or acetamides in good yields. But if the ester (the part of the acid) is
large, e.g. a cyclohexane carboxylic acid ethylester, the yields are bad. One
could first hydrolyze the ester and then do the coupling (e.g. with BoP, PyBoP
or TBTU). But if the ester used herein is hydrolyzed, the formed acid is too
soluble for its isolation of an aquous layer (an tert. amine function is also
present -> IEP aso).
Is there any method for its direct transformation?
(There is a direct method with 2,2,2-trihaloethyl esters using
phosphorous(III) reagents, but I have to avoid the formation of this ester.)

Thank you very much,

samarium 

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