2-Bromoethanol → HCID 86684665, compound

Participants

Reaction Conditions

Reaction Steps

2-Bromo-ethanol (0.61 mL, 8.03 mmol), followed by PPh3 (3.16 g, 12.05 mmol) was added to a solution of Boc-Tyr-OMe (2.85 g, 9.64 mmol) in anhydrous THF (50 mL). The mixture was cooled to 0° C. and DEAD (5.5 mL of 40% wt solution in toluene, 12.05 mmol) was added. The mixture was allowed to warm at room temperature and was stirred overnight. After the reaction was finished, the solvent was evaporated and the residue dissolved in EtOAc (100 mL) was washed with NaOH (0.1 M, 2×50 mL), followed by brine. The organic phase was dried over Na2SO4 and evaporated. The crude product was purified by flash column chromatography (SiO2, step-wise gradient from 2-40% EtOAc in Hexanes) to give 1A (1.61 g, 50%) as a white solid. 1H NMR (600 MHz, CDCl3): δ 7.04 (2H, d, J=8.4 Hz), 6.84 (2H, d, J=8.4 Hz), 4.96 (1H, d, J=7.8 Hz), 4.51-4.58 (1H, m), 4.27 (2H, t, J=6.6 Hz), 3.71 (3H, s), 3.62 (2H, t, J=6.6 Hz), 3.06 (1H, dd, J=13.8, 5.4 Hz), 3.00 (1H, dd, J=13.8, 5.4 Hz), 1.42 (9H, s); 13C NMR (150 MHz, CDCl3): δ 172.3, 157.2, 155.1, 130.4, 128.8, 114.8, 79.9, 67.9, 54.5, 52.2, 37.5, 29.1, 28.3; MS (ESI, m/z): 424 (M+Na)+.

Provenance & Evidence