Chemical Forums
Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: falcon on September 07, 2004, 09:37:38 AM
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Prompt please, how to synthesize 2-aminooxazolidinenone-4
One described method involve interaction a butyl ester of glycolic acid with urea, that results to 2-aminooxazolidinenone-4, but output of a product less than 5%.
I think, may be that there are more "fashionable" methods.
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How about urea + chloroacetyl chloride?
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I have tried so to do, thus was formed
NH2CONHCOCH2Cl but chloromethyl - group did not attack the "urea" carbonyl (at least heating to ~120 `C). May be necessary iodoacetyl chloride (but... :-\ is a very "cheerful" substance). Also I have lead reaction between urea and methyliodoacetate in DMF (isourea derivative -> intramolecular attack imino - group to ester group). I began to heat up and... iodine was allocated. May be air oxidation iodide anion in boiling solution ???
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What conditions did you try to cyclize the product from the chloroacetyl chloride reaction?
How about a DCC coupling with urea and glycolic acid, then treat the product with tosyl chloride + triethylamine. Procedures similar to that are the most common way to make oxazolines.
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After neutralization NH2CONHCOCH2Cl*HCl, heated up at presence NaHCO3 (is described method, but in cases saturated ureas) in ~50% EtOH, cyclization failed. At now I think that It is necessary to use (can be) stronger bases (KOtBu or KOiPr) in DMSO.
As to glycolic acid... is a problem for me. I think to try so: NH2CONHCOCH2Cl -> NH2CONHCOCH2OH ->
as you have offered (MsCl/Et3N).
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Maybe you could try urea + bromoacetyl bromide. That should be significantly more reactive than the chloride version.
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Well, I shall try so to make. Probably this substance should be heated up to ~ 120-150 `C.
About results I shall inform :)