Hydrochloric Acid → (R)-6-(4-fluoro-3-methylbenzyloxy)-2-azidohexanoic acid

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.) solution of (R)-3-((R)-6-(4-fluoro-3-methylbenzyloxy)-2-azidohexanoyl)-4-benzyloxazolidin-2-one (0.251 g, 0.552 mmol) in 11 mL of THF/H2O (8:3), were added stepwise 30% H2O2 (0.22 mL, 2.208 mmol) and LiOH (0.046 g, 1.105 mmol). The reaction mixture was stirred at 0° C. for 1 h then room temperature for overnight. Then a solution of Na2SO3 (0.304 g, 2.412 mmol) in 3 mL of water was added. After stirred at room temperature for 10 min, the reaction mixture was acidified with 4N HCl to pH=2 and extracted with dichloromethane (30 mL×3). The combined organic extracts dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was used directly in the next step without further purification (0.163 g, >99% yield).

Provenance & Evidence