Ethyl Acetate → (2R,5S)-2-benzyl-1,6-bis((S)-4-benzyl-2-oxooxazolidin-3-yl)-5-ethylhexane-1,6-dione

Participants

Reaction Steps

To a solution of (2S,5S,E)-2-benzyl-1,6-bis((S)-4-benzyl-2-oxooxazolidin-3-yl)-5-methylhex-3-ene-1,6-dione (250 mg, 0.431 mmol) in EtOAc (5 mL) was added 10% Pd/C (80 mg, 0.075 mmol). The reaction mixture was purged with nitrogen and stirred under an atmosphere of hydrogen (balloon) overnight. The reaction mixture was filtered through CELITE® and concentrated to afford (2R,5S)-2-benzyl-1,6-bis((S)-4-benzyl-2-oxooxazolidin-3-yl)-5-ethylhexane-1,6-dione (221 mg, 0.379 mmol, 88% yield), which was used without further purification. Anal. Calcd. for C35H38N2O6 m/z 582.3. found 579.2 (M−); 1H NMR (400 MHz, CDCl3) δ ppm 7.35-7.31 (m, 5H), 7.27-7.21 (m, 7H), 7.04-7.02 (m, 3H), 4.68-4.66 (m, 2H), 4.19-4.11 (m, 4H), 4.04 (m, 1H), 3.66 (bs, 1H), 3.32 (m, 1H), 3.05-3.0 (m, 2H), 2.80 (m, 1H), 2.68 (m, 1H), 2.36 (m, 1H), 1.75-1.68 (m, 4H) 1.25 (t, J=7.2 Hz, 2H), 0.92 (t, J=7.2 Hz, 3H).

Provenance & Evidence