反应详情

温度

80 °C

NEt3 (14.2 ml, 102 mmol, 1.3 equiv) and diphenylphosphoryl azide (22 ml, 102 mmol, 1.3 equiv) were added to a suspension of 5-ethoxy-isophthalic acid monomethyl ester (D45) (17.6 g, 78.6 mmol, 1 equiv) in toluene (250 ml) and the mixture heated at 80° C. for 3 h. Benzyl alcohol (12 ml, 118 mmol, 1.5 equiv) was added and the resulting mixture was refluxed for 4 h, cooled to room temperature and concentrated in vacuo. The residue was dissolved in AcOEt (300 ml) and the resulting solution was washed with 2N aqueous HCl solution (100 ml) followed by saturated aqueous NaHCO3 solution (100 ml), dried over MgSO4 and concentrated in vacuo. The residue was triturated with Et2O to give 3-benzyloxycarbonylamino-5-ethoxy-benzoic acid methyl ester (D47) (15 g, 62%) as a white solid. [M−H]−=328.1, RT=3.46 min

1. temperaturethe resulting mixture was refluxed for 4 h
2. temperaturecooled to room temperature
3. concentrationconcentrated in vacuo
4. dissolutionThe residue was dissolved in AcOEt (300 ml)
5. washthe resulting solution was washed with 2N aqueous HCl solution (100 ml)
6. dry with materialdried over MgSO4
7. concentrationconcentrated in vacuo
8. customThe residue was triturated with Et2O