Benzyl chloroformate → HCID 86658527, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of nucleoside 3 (2.52 g, 2.75 mmol) in anhydrous DCM (8 mL) was added DMAP (1.01 g, 8.2 mmol) and the solution was cooled at 0° C. in an ice-water bath. Cbz-Cl (0.77 g, 4.2 mmol) was added via a syringe to the mixture and resulted in a cloudy reaction mixture. The mixture was stirred at room temperature for 24 hours and sat. NaHCO3 (10 mL) was added. The mixture was partitioned in DCM and water. The organic layer was dried over Na2SO4 and concentrated to a white foam solid. The residue was purified via column chromatography (10˜60% EtOAc in hexanes) to afford 2.74 g product, 4, as a white foam solid (yield, 95%). 1H-NMR (CDCl3): δ 7.87 (s, 1H), 7.41-7.16 (m, 24H), 6.79-6.75 (m 8H), 6.28 (s, 1H), 5.65 (br, 1H), 5.15 (s, 2H), 4.28 (d, 1 H), 3.79-3.71 (m, 15H), 3.55-3.52 (m, 1H), 3.39-3.36 (m, 1H), 0.93 (br, 3H).

Provenance & Evidence