Allyl iodide → HCID 68292176, compound

Participants

Reaction Conditions

Reaction Steps

A solution of NaHMDS (1.0 M in THF, 1.34 mL, 1.34 mmol) was slowly added dropwise over 10 min to a −78° C. solution of (S,E)-1,6-bis((S)-4-benzyl-2-oxooxazolidin-3-yl)-2-(4-fluorobenzyl)hex-3-ene-1,6-dione (763 mg, 1.34 mmol) in THF (4.8 mL). After the addition, the reaction mixture was allowed to stir for another 30 min at −78° C. and then a solution of allyl iodide (225 mg, 1.34 mmol) in THF (0.5 mL) was added dropwise. The reaction temperature was then warmed to −40° C. and stirred at −40° C. for 45 min. Then the reaction was warmed to 0° C. and stirred at 0° C. for an additional 1 hr. The reaction was quenched by the addition of saturated NH4Cl. The mixture was then partitioned between EtOAc and water. The organic phase was isolated, washed with saturated aqueous NaCl, dried over MgSO4 and concentrated. The crude product was purified using silica gel chromatography (ISCO system) eluting with a gradient of 0-100% EtOAc/Hex to give (2S,5S,E)-2-allyl-1,6-bis((S)-4-benzyl-2-oxooxazolidin-3-yl)-5-(4-fluorobenzyl)hex-3-ene-1,6-dione (470 mg, 0.770 mmol, 57.6% yield) as a foam. Anal. Calcd. for C36H35FN2O6 m/z 610.2. found: 611.2 (M+H)+.

Provenance & Evidence