Water → O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosine

Participants

Reaction Conditions

Reaction Steps

To a solution of N-Boc-tyrosine (281 mg, 1.0 mmol) in methanol (0.5 mL) were added 28% sodium methoxide-methanol solution (0.42 mL, 2.1 mmol), benzyl chloride (115 μL, 1.4 mmol) and tetrabutylammonium iodide (28 mg) and the mixture was stirred at 40° C. for 24 hr. Then, water (2 mL) was added to make the system homogeneous, which system was then analyzed by HPLC (conversion yield 89%). The aqueous solution was washed with toluene (0.5 mL), neutralized with hydrochloric acid to allow precipitation of a solid, and the solid was filtered and dried to give the objective N-Boc-(O-benzyl)tyrosine (312 mg, yield 84%).

Provenance & Evidence