Chloroacetyl chloride → (3S)-5-Oxo-4-(phenylmethyl)-3-morpholinecarboxylic acid

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Reaction Steps

To a solution of (S)-2-(benzylamino)-3-hydroxypropanoic acid (40.0 g, 205 mmol) in tetrahydrofuran (600 mL) was added aqueous potassium carbonate solution (85.0 g, 600 mL) at 0° C. under nitrogen atmosphere, and additionally, chloroacetylchloride (29.0 mL, 369 mmol) was added. After stirring for 2 hours at room temperature, to the mixture was added 30% aqueous sodium hydroxide solution to adjust to pH 13. To the mixture was added diethyl ether, and the organic layer was separated, and then concentrated hydrochloric acid was added to adjust to pH 1, and cooled to 0° C. The precipitated crystal was collected by filtration to give the title compound (29.0 g, 123 mmol, 60%).

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