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

Temperature

-78 °C

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).

1. additionwas added dropwise
2. temperatureThe reaction mixture was warmed to rt
3. stirringto stir overnight
4. extractionthe crude product was extracted with EtOAc (4×5 mL)
5. customThe organic layer was separated
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated
8. customto afford the crude product, which
9. customwas purified

ORD record

ord-79d5a078d5d44edf96dd42a888c1915f

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09346852B2