Iodoethane → (2S,5S,E)-2-benzyl-1,6-bis((S)-4-benzyl-2-oxooxazolidin-3-yl)-5-ethylhex-3-ene-1,6-dione

Participants

Reaction Conditions

Reaction Steps

To a solution of (S,E)-2-benzyl-1,6-bis((S)-4-benzyl-2-oxooxazolidin-3-yl)hex-3-ene-1,6-dione (600 mg, 1.08 mmol) in THF (50 mL) at −78° C., a solution of NaHMDS (1 M in THF, 1.4 mL, 1.4 mmol) in diluted with THF (2.5 mL) was added dropwise. The reaction mixture was stirred for 1 hr at −78° C. and ethyl iodide (1.70 g, 10.9 mmol) was added dropwise. The reaction mixture was warmed to rt and allowed to stir overnight. Saturated aqueous NH4Cl (3 mL) was added to the reaction mixture and the crude product was extracted with EtOAc (4×5 mL). The organic layer was separated, dried (Na2SO4) and concentrated to afford the crude product, which was purified using silica gel chromatography to afford (2S,5S,E)-2-benzyl-1,6-bis((S)-4-benzyl-2-oxooxazolidin-3-yl)-5-ethylhex-3-ene-1,6-dione (100 mg, 0.172 mmol, 16% yield). Anal. Calcd. for C35H36N2O6 m/z 580.3. found 579.2 (M−); 1H NMR (400 MHz, CDCl3) δ ppm 7.33-7.29 (m, 5H), 7.27-7.24 (m, 5H), 7.19-7.16 (m, 3H), 7.05 (m, 2H), 5.7 (dd, 1H), 5.58 (dd, 1H), 4.71 (q, 1H), 4.66-4.57 (m, 2H), 4.20-4.07 (m, 6H), 3.27-3.19 (m, 2H), 3.08 (m, 1H), 2.82 (m, 1H), 2.71 (m, 1H), 2.58 (m, 1H), 1.8-1.75 (m, 1H), 1.52-1.45 (m, 1H), 0.81 (t, J=7.6 Hz, 3H).

Provenance & Evidence