Benzyl Bromide → N-t-Butoxycarbonyl Statine benzyl ester

Participants

Reaction Steps

N-(t-butyloxycarbonyl)-statine (1141 mg., 5.12 mmol) were dissolved in 20 ml of dimethylformamide. 708 mg. of potassium carbonate and 0.609 ml of benzyl bromide was then added. After the reaction was complete, the reaction mixture was concentrated, taken up in ethyl acetate, washed twice with 5 ml of H2O, dried over MgSO4, filtered and concentrated to yield 1510 mg of a yellow oil (81% yield). 1H NMR, 90 mHz, CDCl3, partial, 0.92 (d, J=7 Hz, 6H), 1.42 (s, 9H, Boc), 2.58 (m, 2H), 4.05 (m, 1H), 4.72 (d, BocNH, 1H), 5.13 (s, CH20, 2H), 7.3 (s, 5H, aromatic).

Provenance & Evidence