Acetic Acid → HCID 21472087, compound

Participants

Reaction Steps

To a stirring solution of 1-(2-propyl)-5-(2,2,2-trifluoroethyl)-1,5-benzodiazepine-2,4-dione (440 mg, 1.46 mmole) in tetrahydrofuran (12 mL), which was cooled to -78° C. in a dry ice/acetone bath, was added dropwise potassium tert-butoxide (1M in tetrahydrofuran, 1.61 mL, 1.61 mmole). After ten minutes, 2,4,6-triisopropylbenzenesulfonyl azide (495 mg, 1.61 mmole) in tetrahydrofuran (5 mL) was added dropwise. After ten minutes, acetic acid (0.35 mL,5.84 mmole) in tetrahydrofuran (5 mL) was added in one portion and the reaction was warmed to room temperature over three hours. The reaction was poured into a solution of saturated sodium hydrogen carbonate (200 mL) and extracted with ethyl acetate (3×100 mL). The organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 1:3 ethyl acetate:hexane to give 350 mg of product identified as the axial conformer and 35 mg of the equatorial isomer. NMR data is given for the major isomer.

Provenance & Evidence