Triethylamine → Bromoacetylphenylalanine ethyl ester

Participants

Reaction Conditions

Reaction Steps

Under argon, bromoacetyl bromide (0.89 g, 10.2 mmol) in chloroform (10 mL) was added dropwise to a mixture of chloroform (40 mL), L-phenylalanine ethyl ester (2.3 g, 10 mmol), and triethylamine (3 mL), which was pre-cooled to −30° C. The mixture was stirred at r.t. for a further 2 hrs, and then washed with aqueous saturated potassium carbonate solution and water, then dried over sodium sulfate. The solvents were removed under reduced pressure, giving a dark oil, which was dissolved in a mixture of DCM (100 mL) and hexane (300 mL), form which a crystalline solid deposited. The crystals were dried in air, giving colourless needles (2.7 g, 79%). 1H-NMR (CDCl3): 7.29-7.31 (3H, m, Ar), 7.11-7.16 (2H, m, Ar), 4.79-4.89 (1H, m, α-H), 4.20 (2H, q, J 7.2, OCH2CH3), 3.86 (2H, s, BrCH2), 3.16 (2H, d, J 5.8, ArCH2), 1.26 (3H, t, J 7.2, OCH2CH3). m/z (ES+): 336 [M+Na]+.

Provenance & Evidence