反应详情

温度

100 °C

Anthranilic acid (2.0 g, 14.6 mmol), 3-phthalimidopropionic acid (3.2 g, 14.6 mmol), and triphenylphosphite (4.0 mL, 15.3 mmol) were dissolved in pyridine (20 mL) and heated in a sealed tube at 100° C. for 2 hours. After cooling to room temperature, the tube was opened, p-anisidine (2.7 g, 21.9 mmol) was added and heating at 100° C. was resumed for 4 hours. The pyridine was removed by azeotroping with toluene, and the residue was suspended in CHCl3 and toluene. The solids that crashed out were removed, and the residue was purified by silica gel chromatography with gradient elution (0 to 100% EtOAc in hexanes). A white solid precipitated from several of the fractions which was isolated by filtration to provide A-1 (2.23 g, 36%). Data for A-1: LRMS: calculated M+H for C25H19N3O4: 426.14. Found: 426.16.

1. temperatureAfter cooling to room temperature
2. temperatureheating at 100° C.
3. customThe pyridine was removed
4. customby azeotroping with toluene
5. customThe solids that crashed out were removed
6. customthe residue was purified by silica gel chromatography with gradient elution (0 to 100% EtOAc in hexanes)
7. customA white solid precipitated from several of the fractions which
8. customwas isolated by filtration
9. customto provide A-1 (2.23 g, 36%)