docberto
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Friedel Crafts acylation with amino acids question
Would it be possible to do acylation with an amino acid that isn't N-protected? I know an acyl halide or acyl anhydride would readily react with
any available nitrogen. But would the N-protection be necessary when using the acid itself and using polyphosphoric acid or P2O5 as the Lewis acid?
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stoichiometric_steve
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i think that lewis acids might most likely catalyze the formation of peptides as well.
Aluminium Tungstophosphate may do the job, or may not. experiment is king.
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solo
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Just look at the Dakin-West Reaction and you will see that that both the COOH and the NH2 will get acylated unless you protect the amine group aside
you need a strong base to do the deed.....see March 5th edition page 812 under "Replacement of a Carboxyl Group by an Acyl Group".........solo
[Edited on 27-12-2007 by solo]
It's better to die on your feet, than live on your knees....Emiliano Zapata.
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