Methyl iodide → (2S,5S,E)-2-benzyl-1,6-bis((S)-4-benzyl-2-oxooxazolidin-3-yl)-5-methylhex-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 (250 mg, 0.450 mmol) in THF (50 mL) at −78° C., a solution of NaHMDS (1 M in THF, 0.54 mL, 0.54 mmol) in diluted in THF (2.5 mL) was added dropwise. The reaction mixture was stirred for 1 hr at −78° C. and then methyl iodide (0.078 g, 0.55 mmol) was added in two portions. The reaction mixture was warmed to rt and allowed to stir overnight. Saturated aqueous NH4Cl (3 mL) was added to the reaction mixture and crude product was extracted with ethyl acetate (5 mL). The organic layer was separated, dried (Na2SO4) and concentrated to afford 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-methylhex-3-ene-1,6-dione (137 mg, 0.243 mmol, 54% yield). Anal. Calcd. for C34H34N2O6 m/z 566.2. found 565.2 (M−): 1H NMR (400 MHz, CDCl3) δ ppm 7.36-7.30 (m, 5H), 7.29-7.26 (m, 5H), 7.25-7.18 (m, 3H), 7.08-7.05 (m, 2H), 5.75-5.62 (m, 2H), 4.72-4.57 (m, 3H), 4.36-4.29 (m, 1H), 4.23-4.12 (m, 4H), 3.28-3.21 (m, 2H), 3.10 (m, 1H), 2.84 (m, 1H), 2.76 (m, 1H), 2.61 (m, 1H), 1.24 (d, J=6.8 Hz, 3H).

Provenance & Evidence