Acetic Acid → HCID 22312185, compound

Participants

Reaction Steps

To a stirring solution of 1,5-bis-(2-propyl)-1,5-benzodiazepin-2,4-dione (500 mg, 1.92 mmole) in tetrahydrofuran (25 mL), which was cooled to -78° C. in a dry ice/acetone bath, was added dropwise potassium bis(trimethylsilyl) amide (0.5M in toluene, 4.6 mL, 2.3 mmole). After ten minutes, 2,4,6-triisopropylbenzenesulfonyl azide (708 mg, 2.0 mmole) in tetrahydrofuran (5 mL) was added dropwise. After ten minutes, acetic acid (0.44 mL, 7.7 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 315 mg of an isomer that is identified as the axial azide, and 120 mg of a lower rf isomer identified as the equatorial conformer. NMR dam for the major isomer is:

Provenance & Evidence