PURPOSE: To obtain the titled compound useful as an antiarrhythmic agent easily in high yield at a low cost, by reacting 3-isopropylamino-1,2-propanediol as a starting material with ethyl carbonate, and converting the resultant novel intermediate oxazolidinone derivative into the titled compound.
CONSTITUTION: 3-Isopropylamino-1,2-propanediol of formulaIis reacted with ethyl carbonate to give a 5-hydroxymethyl-3-isopropyl-2-oxazolidinone of formula II, which is then reacted with p-toluenesulfonyl chloride in pyridine at room temperature to afford a compound of formula III. The resultant compound of formula III is reacted with an alkaline metallic salt of 2-allylphenol in DMF at 60W100°C to give a compound of formula IV, which is then refluxed in a mixed solution of 4N- NaOH-ethanol (1:3) to afford the aimed compound of formula V. The optimal concentration of the alkali is such that the final concentration of 1N is reached. The concentration higher than the valve or a temperature of 100°C or above causes the isomerization of the alkyl group.
MIZUKOSHI SEISHI
KOMATSU OSAMU
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