Water → HCID 86607071, compound

Participants

Reaction Steps

To (4-acetyl-2-{[(allyloxy)carbonyl]amino}phenyl)acetic acid (10.9 g) prepared by step g) and triethylamine (11 mL) in DMF (100 mL) was added at room temperature p-nitrobenzyl bromide (17.0 g), and the mixture was stirred at room temperature for 1 hour. To the reaction mixture were added saturated brine (500 mL) and water (300 mL), and the mixture was extracted with ethyl acetate (200 mL, 2×100 mL). The organic layers were combined, washed with saturated brine (100 mL), dried over magnesium sulfate, filtered and the solvent was removed in vacuo. The residue was purified with column chromatography (SiO2 300 g, hexane/ethyl acetate/chloroform=3:1:4˜0:1:1) to give the object compound (16.4 g, 98%) as a pale brown solid. Further the product was recrystallized from chloroform/hexane to give the object compound (10.4 g, 64%) as a white solid.

Provenance & Evidence