Reacción #8903

Ecuación de reacción

product

N′-[6-(2-Chlorophenyl)-5-(4-chlorophenyl)-2-(2,2-dimethylpropanoyl)-furo[2,3-b]pyridin-3-yl]-N-(2-hydroxyethyl)-N-methylethanediamide

triphenylphosphine

diisopropylazodicarboxylate

→

title compound

1-[6-(2-Chlorophenyl)-5-(4-chlorophenyl)-2-(2,2-dimethylpropanoyl)-furo[2,3-b]pyridin-3-yl]-4-methylpiperazine-2,3-dione

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe reaction mixture was stirred an additional 1 h at room temperature
2. 2
   Otroevaporated to dryness
3. 3
   OtroThe residue was purified on a silica gel flash chromatographic column
4. 4
   Lavadoeluted with 0–75% EtOAc-hexane
5. 5
   OtroEvaporation of the purified fractions
6. 6
   Otrodrying in vacuo

Procedimiento

A 10 mL rb flask was charged with a solution of 0.075 g (0.13 mmol) of the product of Step A and 0.052 g (0.2 mmol) triphenylphosphine in 2 mL THF. The reaction mixture was stirred at 0° C. and 39 μL of diisopropylazodicarboxylate was added dropwise. The reaction mixture was stirred an additional 1 h at room temperature, then evaporated to dryness. The residue was purified on a silica gel flash chromatographic column eluted with 0–75% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded the title compound. HPLC/MS: 550.0 (M+1), 551.9 (M+3); Rt=3.95 min.

Fuente