Acetic Acid → 3-Azido-9-chloro-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-1,4-benzodiazepine

Participants

Reaction Steps

A solution of 9-chloro-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-1,4-benzodiazepine (0.287 g, 0.813 mmol) in tetrahydrofuran (10 mL) was cooled to −78° C., and potassium t-butoxide (0.905 mL, 1 M in tetrahydrofuran) was added. After 15 min, 2,4,6-triisopropylbenzenesulfonylazide (0.976 mL, 1M in tetrahydrofuran) was added. After 15 min, acetic acid (0.186 mL, 3.2 mmol) was added and the reaction warned to room temperature and stirred for 3.5 h. Workup with ethyl acetate and saturated sodium bicarbonate solution, followed by saturated brine and drying gave a solid. Tetrahydrofuran (30 mL) was added, the solid filtered, and the filtrate concentrated to obtain the title compound. MS 394 (M+1) 1H NMR (500 MHz, CDCl3) δ 7.77–7.20 (m, 8H), 6.40 (s, 1H), 5.20 (m, 1H), 4.30 (m, 1H).

Provenance & Evidence