Dimethylformamide → HCID 15127717, compound

Participants

Reaction Conditions

Reaction Steps

Following the procedure of Boger and Yohannes (J. Org. Chem. 53, 487 (1988), a solution of N-BOC-4-iodophenylalanine (391 mg, 1 mmol) and methyl iodide (156 μL, 2.5 mmol) in tetrahydrofuran (5 mL) at 0° C. was added 60% sodium hydride in oil suspension (100 mg, 2.5 mmol). The resulting mixture was stirred at 0° C. for 1 hr and then at room temperature for 16 hr. Added dimethylformamide (1 mL) and additional methyl iodide (156 μL, 2.5 mmol) and 60% sodium hydride (100 mg, 2.5 mmol) and heated at 75° C. overnight. The reaction was worked up as described in the reference to yield N-BOC-N-methyl-4-iodophenylalanine.

Provenance & Evidence