Sodium bis(trimethylsilyl)amide → HCID 68292731, compound

Participants

Reaction Conditions

Reaction Steps

A solution of NaHMDS (1.0 M in THF, 0.258 mL, 0.258 mmol) was added dropwise to a −78° C. solution of (S,E)-2-allyl-1,6-bis((S)-4-benzyl-2-oxooxazolidin-3-yl)hex-3-ene-1,6-dione (118 mg, 0.235 mmol) in THF (1.0 mL). After stirring at −78° C. for 40 min, a solution of 1-(benzyloxy)-4-(bromomethyl)benzene (78 mg, 0.282 mmol) in THF (0.2 mL) was added dropwise. The reaction temperature was then slowly raised to 0° C. over 45 min. After 30 min at 0° C., the reaction temperature was allowed to reach rt. After 2 h at rt, the reaction mixture was quenched by addition of saturated NH4Cl. The mixture was 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-(benzyloxy)benzyl)hex-3-ene-1,6-dione (47 mg, 0.067 mmol, 29%) as a white solid. Anal. Calcd. for C43H42N2O7 m/z 698.2. found: 699.2 (M+H)+.

Provenance & Evidence