1,1'-Carbonyldiimidazole → 2-Phenylglycine

Participants

Reaction Steps

To a solution of N-Boc L-phenylglycine (2.51 g, 10 mmol) in acetonitrile (50 ml), was added portionwise 1,1′-carbonyldiimidazole (3.24 g, 20 mmol). The solution was stirred at room temperature for 1 h, oleyl alcohol (3.15 ml, 2.68 g, 10 mmol) was added, and the reaction mixture further stirred for 2 h at room temperature. The solvent was evaporated, the residue was dissolved in ethyl acetate (150 ml), washed successively with 5% NaHCO3, 5% citric acid and water, dried on MgSO4 and evaporated to dryness. The residue was dissolved in 1% HCl in ethyl acetate (100 ml), and the solution set aside for 6 h at room temperature, and evaporated to dryness. The residue thus obtained was crystallized from ether/n-hexane to give 1.6 g 3.65 mmol, 36.5% yield) of an off-white solid, mp 101-103° C. Racemic mixture was attained.

Provenance & Evidence