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Topic: 2-aminooxazolidinenone-4  (Read 5551 times)

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falcon

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2-aminooxazolidinenone-4
« on: September 07, 2004, 09:37:38 AM »
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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Re:2-aminooxazolidinenone-4
« Reply #1 on: September 07, 2004, 01:17:16 PM »
How about urea + chloroacetyl chloride?

falcon

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Re:2-aminooxazolidinenone-4
« Reply #2 on: September 08, 2004, 03:47:04 AM »
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  ???
« Last Edit: September 08, 2004, 03:49:05 AM by falcon »

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Re:2-aminooxazolidinenone-4
« Reply #3 on: September 08, 2004, 11:58:08 AM »
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.

falcon

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Re:2-aminooxazolidinenone-4
« Reply #4 on: September 09, 2004, 02:55:09 AM »
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).
« Last Edit: September 09, 2004, 02:56:58 AM by falcon »

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Re:2-aminooxazolidinenone-4
« Reply #5 on: September 09, 2004, 12:20:28 PM »
Maybe you could try urea + bromoacetyl bromide.  That should be significantly more reactive than the chloride version.

falcon

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Re:2-aminooxazolidinenone-4
« Reply #6 on: September 11, 2004, 02:19:04 AM »
Well, I shall try so to make. Probably this substance should be heated up to ~ 120-150 `C.
About results I shall inform  :)

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