4-Methoxyphenylacetic Acid → HCID 22449691, compound

Participants

Reaction Steps

4-Methoxyphenylacetic acid (11.5 g, 69.4 mmol) was suspended in toluene (200 ml) and then admixed sequentially with triethylamine (11.6 ml, 85.2 mmol) and diphenylphosphoric azide (17.9 ml, 85.2 mmol). The reaction mixture was stirred at room temperature for 1 hour, and then heated under ref lux for 3 hours. The mixture was combined with dimethyl 3-aminophthalate (13.1 g, 62.4 mmol) obtained in Reference Example 102 and then heated under reflux further for 20 hours. The solvent was distilled off under reduced pressure, and the residue was combined with water and extracted with ethyl acetate. After the extract was washed with water and dried (MgSO4), the solvent was distilled off under reduced pressure. The residue was subjected to a column chromatography on a silica gel eluted with n-hexane-ethyl acetate (10:1, v/v) to give the title compound (8.49 g, 40%) as a white crystal. This product was used in the next reaction without further purification.

Provenance & Evidence