From: Robert Schuit (rcschuit$##$hotmail.com)
Date: Thu Jun 10 1999 - 12:44:16 EDT
Dear all
I work in a small lab and we synthesis isotopically labelled compounds for
studies and diagnostic purposes in the field of metabolic disorders. With
this compounds as an internal standard for GCMS we can measure metalolites
in plasma, urine etc. One of the compounds we have to synthesis now is
labelled methylcitrate, this is for sale (100 mg for $3000). So a bit to
much.
In literature there are different approaches written.
1) Starting for Acetondicarboxylate, methylate this with NaOMe/CH3I,
(this was unsuccessfull) followed by the cyano-hydrin reaction etc.
2) Reformatsky type reactions with oxalacetate/ethylbromopropionate.
and some more possibilities.
So I thought maybe direct methylation of citric acid. Protected as three
ethylester and the OH-function as MOM-ether. I tried to abstact the
alphaproton with NaH followed by CH3I etc. Checking the product with GCMS
showed elimination products.
My question is can anyone give advise accordding to the base, protections
groups and so on
Hope to hear something
Kind regards,
Robert C. Schuit
Amsterdam, The Netherlands
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