CrimpJiggler
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N-Acetylation of taurine
Heres taurine:
and heres acamprosate, its acetylated analogue:
From what I read, esters can be used instead of acid anhydrides or acyl halides for N-acylations. So if one were to reflux a solution of taurine in
ethyl acetate, would acamprosate and ethanol be produced?
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Prometheus23
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Esters can indeed be used to n-acylate amines. Ethyl acetate would probably work fine, and even esters like aspirin can sometimes be used.
The only probably is that acamprosate is not n-acetyltaurine but n-acetylhomotaurine. So you would need to use homotaurine instead of taurine for the
synthesis.
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DraconicAcid
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Taurine, however, is not HOS(O)2CH2CH2NH2 (as you've drawn it), but the zwitterion
-O3SCH2CH2NH3+, with a negative charge on the sulphate end and a positive charge on
the nitrogen. I expect that you'd need to deprotonate the nitrogen before it reacted with the ester.
[Edited on 12-4-2013 by DraconicAcid]
Please remember: "Filtrate" is not a verb.
Write up your lab reports the way your instructor wants them, not the way your ex-instructor wants them.
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unionised
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I wonder if ethyl acetate would be likely to acetlyate the nitrogen or ethylate the sulphonic acid.
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DraconicAcid
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If you had the anion, the nitrogen would be far more nucleophilic than the sulphate end. I don't think the acetyl-sulphate compound would form (and
if it did, it would be very reactive towards nucleophiles).
Please remember: "Filtrate" is not a verb.
Write up your lab reports the way your instructor wants them, not the way your ex-instructor wants them.
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Prometheus23
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Yes the taurine or homotaurine would obviously need to be in the anionic state to react with ethyl acetate. And I agree with DraconicAcid, I don't
think the sulfonate group would react with the ethyl acetate to any appreciable amount.
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CrimpJiggler
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Whoops, I didn't notice that extra carbon in acamprosate. Homotaurine isn't as readily available as taurine.
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Nicodem
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Thread Moved
13-4-2013 at 00:00 |
ScienceSquirrel
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Homotaurine is cheaply and readily made;
http://www.nrcresearchpress.com/doi/pdf/10.1139/v62-339
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