Benzyl Bromide → Boc-Azidoalanine benzyl ester

Participants

Reaction Steps

Boc-azidoalanine 8 (520 mg, 2.26 mmol) was dissolved in dry acetonitrile (8 mL) in glass vial equipped with a magnetic stir bar and capped with a septum. Benzyl bromide (325 μL, 2.71 mmol) and diisopropylethylamine (440 μL, 2.49 mmol) were subsequently added via syringe. The solution was stirred for 18 h at room temperature until TLC indicated the consumption of the starting material. The reaction mixture was concentrated in vacuo and the crude product was loaded onto a silica gel column. The column was eluted first with 10% ethyl acetate/hexane to wash off the residual benzyl bromide and then with 20% ethyl acetate/hexane to elute the product (452 mg, 63% yield).

Provenance & Evidence