2-Mesitylenesulfonyl chloride → Benzyl N-[methyl(3-phenyl-4,5-dihydro-1,2-oxazol-5-yl)phosphoryl]glycinate

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Reaction Steps

1.1 g (5 mmol) of 3-phenyl-2-isoxazolin-5-yl(P-methyl)phosphinic acid are dissolved in 20 ml of pyridine and, while cooling in ice, 1.5 g (7 mmol) of mesitylsulfonyl chloride and 0.5 g (7 mmol) of tetrazole are added, and the mixture is then stirred at room temperature for 30 minutes. 1.7 g (5 mmol) of glycine benzyl ester toluenesulfonate are added, and stirring at room temperature is continued with the course of the reaction being followed by thin-layer chromatography. After the reaction is complete, water and half-concentrated potassium bisulfate solution are added to pH 2, the mixture is extracted three times with dichloromethane, and the organic phase is washed with water, dried and concentrated. The pure product is obtained with a melting point of 132° to 135° C. by chromatography on silica gel with dichloromethane/methanol mixtures as mobile phases.

Provenance & Evidence