L-Glutamine → L-Glutamine, N2-[(phenylmethoxy)carbonyl]-

Participants

Reaction Conditions

Reaction Steps

Glutamine (1.84 g, 12.62 mmol) was dissolved in 1 N NaOH (12.58 mL) and the solution was cooled to 0° C. and stirred for 30 min, when Na2CO3 (3.30 g) and benzyl chloroformate (4.38 mL) in dioxane (19.30 mL) were gradually added, in equal portions. Stirring continued at 0° C. for 1 h, then the solution was allowed to stir overnight at room temperature and was extracted with ethyl ether (2×20 mL). The aqueous solution was acidified with 2N HCl to pH 5 and extracted with ethyl acetate (3×50 mL), which was dried over sodium sulfate, and evaporated to give an oil which crystallized overnight. Recrystallization of the crude product gave a white crystalline material (3.07 g, 87%); FABMS 319.1 (M+K), 281.1 (M+H).

Provenance & Evidence