Allyl bromide → HCID 68292782, compound

Participants

Reaction Conditions

Reaction Steps

A solution of NaHMDS (1.0 M in THF, 0.313 mL, 0.313 mmol) was slowly added dropwise over 5 min to a −78° C. solution of (S,E)-1,6-bis((S)-4-benzyl-2-oxooxazolidin-3-yl)-2-(3-fluorobenzyl)hex-3-ene-1,6-dione (170 mg, 0.298 mmol) in THF (1.6 mL). After addition the reaction mixture was allowed to stir for another 25 min at −78° C. and then allyl bromide (108 mg, 0.894 mmol) was added dropwise. The reaction temperature was then slowly raised to 0° C. over 20 min and then stirred at 0° C. for an additional 1 hr. The reaction was quenched by 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-(3-fluorobenzyl)hex-3-ene-1,6-dione (46 mg, 0.075 mmol, 25% yield) as a foam. Anal. Calcd. for C36H35FN2O6 m/z 610.2. found: 611.0 (M+H)+.

Provenance & Evidence