Pyridine → (S)-Benzyl 2-(2-oxooxazolidin-4-YL)acetate

참여 물질

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반응 단계

The alcohol 2 (500 mg, 1.616 mmol) was azeotroped with toluene, and then dissolved in dichloroethane (5 mL). Pyridine (1.44 mL, 17.78 mmol) was added and the mixture was cooled to 0° C. Anhydrous p-toluenesulfonic anhydride (580 mg, 1.778 mmol) was added and the mixture was warmed to room temperature and stirred for 1 hour. A condenser was adapted to the reaction flask and the mixture heated to 90° C. for two hours. Added additional 0.5 equivalents (290 mg) of p-toluenesulfonic anhydride and heated at 90° C. overnight. The mixture was cooled, diluted with dichloromethane and washed with 1 N HCl (2×3 mL), then water. The organic layer was dried with sodium sulfate and filtered over a small silica plug, rinsing with ethyl acetate. The solvents were removed in vacuo to afford an oil that crystallizes. LC-MS m/z=253 (M+NH4+).

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