Hydrochloric Acid → 2-(3-Bromophenyl)-2-((tert-butoxycarbonyl)(methyl)amino)acetic acid

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Reaction Steps

To a solution of (3-bromo-phenyl)-tert-butoxycarbonylamino-acetic acid (490 mg, 1.49 mmol) in THF (10 mL) at room temperature was added sodium hydride (125 mg, 60% inmineral oil, 3.1 mmol) and the resulting pale yellow suspension was stirred at room temperature for 3 hours. Methyl iodide (528 mg, 3.7 mmol) was added and the resulting mixture was stirred overnight. Satuated sodium chloride (10 mL) was added and the aqueous phase pH was adjusted to 5 by addition of 1 N hydrochloric acid. The resulting mixture was extracted with ethyl acetate (10 mL×3) and the combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was purified using a gradient of methanol in dichloromethane to afford (3-bromo-phenyl)-(tert-butoxy-carbonyl-methyl-amino)-acetic acid (390 mg, 76%) as an oil. MS: m/z 344 (M+H+).

Provenance & Evidence