Thionyl Chloride → {[5-Bromo-2-({3-Chloro-4-[(2-methylphenyl)carbonyl]phenyl}amino)benzyl]oxy}ethyl (diethoxyphosphoryl)acetate

Participants

Reaction Steps

The reactions were performed under an argon atmosphere using oven dried glass ware. Diethylphosphonoacetic acid (0.053 mL, 0.33 mmol) was dissolved in dry toluene (2 mL) and thionylchloride (0.065 mL, 0.9 mmol) was added. The reaction mixture was refluxed for 2 h and then concentrated in vacuo. Compound 158 (0.14 g, 0.3 mmol) was dissolved in dry THF (1.5 mL). 4-N,N-dimethylaminopyridine (0.073 g, 0.6 mmol) was added followed by addition of the above acid chloride dissolved in THF(1.5 mL). The reaction mixture was heated at reflux temperature for 20 h. The reaction mixture was diluted with EtOAc and aqueous NaHCO3, and the organic phase was washed with H2O and brine, and the combined water phases were extracted with EtOAc. The combined organic phases were dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography using EtOAc/petroleum ether 2:1 as the eluent to afford the title compound as a slightly coloured oil.

Provenance & Evidence