Sodium Thiosulfate → HCID 67278976, compound

Participants

Reaction Conditions

Reaction Steps

N-Chlorosuccinimide (2.28 g, 17.1 mmol) was added to a solution of (R)-4-(1-acetamidoethyl)-2-methoxyphenyl acetate (2.86 g, 11.4 mmol) in DMF (50 mL) and the mixture was stirred for 1 hour at 0° C. and then for 15 hours at room temperature. The reaction mixture was poured onto aqueous 20% sodium thiosulfate solution and extracted with DCM 3 times. The combined organic layer was dried over sodium sulfate, filtered and evaporated. The residue was chromatographed on a column of silica gel, eluting with EtOAc-Hexane (1:1) and then MeOH-DCM (1:10), to give a brown solid. The solid was washed with Et2O and dried in vacuo to give the title compound (2.40 g, 74%) as white solid. 1H NMR (270 MHz, CDCl3) δ ppm 1.51 (3H, d, J=7.2 Hz), 2.00 (3H, s), 2.30 (3H, s), 3.83 (3H, s), 5.20-5.40 (1H, m), 5.91 (1H, m), 6.91 (1H, s), 7.06 (1H, s).

Provenance & Evidence