Methyl iodide → (2R)-2-[(methoxycarbonyl)amino]-3-methyl-3-(methylsulfanyl)butanoic Acid

Participants

Reaction Conditions

Reaction Steps

A solution of L-penicillamine (0.5 g, 3.35 mmol) in methanol (3.3 mL) at 0° C. was treated with aqueous NaOH solution (3.7 mL, 1 N) and methyl iodide (0.23 mL, 3.69 mmol), stirred at 0° C. for 16 hours, treated with additional aqueous NaOH solution (3.5 mL, 3 N) at 0° C., followed by methyl chloroformate (0.5 mL, 6.47 mmol), warmed to 25° C. and stirred for 3 hours, and partitioned between ethyl acetate and water. The organic phase was washed with brine and dried over MgSO4, filtered and concentrated to give the title compound (0.428 g, 58% yield), which was used without further purification.

Provenance & Evidence