Acetic Acid → 3-Azido-5-phenyl-1-(2,2,2-trifluoroethyl)-1H-benzo[e][1,4]diazepine-2-one

Participants

Reaction Steps

To a stirring solution of 5-phenyl-1-(2,2,2-trifluoroethyl)-1H-benzo[e][1,4]diazepine-2-one (66 g,0.209 mole) in THF (1200 mL) cooled to -78° C. was added potassium tert-butoxide (229 mL of a 1N solution in THF dropwise over 30 min. A solution of the anion was obtained. A solution of 2,4,6-triisopropylbenzenesulfonylazide (71 g, 0.229 mole) in THF (200 mL) was added over 20 min. This was stirred for 10 min, acetic acid (50 g, 48 ml, 0.834 mole) was added and the reaction allowed to warm to ambient temperature over 4 hours. The reaction was poured into sat. NaHCO3 (1 L) and extracted with ethyl acetate (2×500 mL). The organic layers were combined, washed once with water then brine, dried with Na2 SO4 and evaporated at reduced pressure. The residue was dissolved in THF (500 mL) and then filtered to give a solid which was discarded. The solution of crude azide was used without further purification.

Provenance & Evidence