To a solution of (S)-2-(tert-butoxycarbonylamino)-4-hydroxybutyric acid 206 (8.5 g, 38 mmol) in DMF (50 mL) was added K2CO3 (5.24 g, 38 mmol) and iodomethane (5.4 g, 38 mmol). The reaction mixture was stirred at room temperature overnight. After the reaction was completed, the reaction mixture was diluted with water (500 mL) and extracted with dichloromethane (500 mL). The organic layers were combined, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to remove the solvent to afford the crude product (S)-2-((tert-butoxycarbonyl)amino)-4-hydroxybutyric acid methyl ester 207 (8.5 g, 90% yield).
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