Pyridine → HCID 19385025, compound

Participants

Reaction Steps

A solution of 868 mg (3.22. mmol) of Cbz amine from Example 3 in 15 mL of dichloromethane was cooled to 0° C. and treated with 0.286 mL (3.54 mmol) of pyridine followed by 569 mg (0.41 mL, 3.22 mmol) of benzenesulfonyl chloride. The reaction mixture was stirred at room temperature for 2 h and then partitioned between chloroform and water. The organic phase was washed sequentially with 5% aqueous hydrochloric acid and saturated aqueous sodium bicarbonate, dried over magnesium sulfate, and concentrated. Purification by recrystallization from ethyl acetate/hexane gave 630 mg (48%) of the title compound as a white solid: 1H NMR (400 MHz, CDCl3) 7.72 (d, 2H, J=7.2 Hz), 7.48 (m, 1H), 7.39 (m, 2H), 7.33 (m, 5H), 7.02 (d, 2H, J=8.3 Hz), 6.95 (d, 2H, J=8.3 Hz), 6.55 (s, 1H), 5.06 (s, 2H), 4.68 (broad s, 1H), 3.37 (m, 2H), 2.72 (t, 2H, J=6.9 Hz). FAB MS m/z 411 (M+1).

Provenance & Evidence