反应详情

(Scheme 3 (Q)) Diphenylphosphoryl Azide (0.083 ml, 0.38 mmole) was added to a suspension of starting material 2-methyl-7-(2-methyl-4,5-diphenyl-imidazol-1-yl)-heptanoic acid (120 mg, 0.32 mmole) and Triethylamine (0.14 ml, 1.005 mmole) in Toluene (5 ml) at room temperature. The reaction mixture was let stirred at room temperature for 10 minutes under Nitrogen, then at 108° C. for 90 minutes. The reaction was let cooled to room temperature, to which 2-Fluorophenol (0.03 ml, 0.038 g, 0.338 mmole) was added. The reaction mixture was let stirred at room temperature for 30 minutes, then at 100° C. for 18 hrs. The next day, analysis by TLC (Dichloromethane/Ethyl Acetate 3:1) indicated consumption of starting material. The reaction was let cooled to room temperature, where the solvent was removed by rotorvap. The crude material was purified by flash column chromatography using Dichloromethane/Ethyl Acetate (6:1 to 3:1). Product was obtained (110 mg, 71%). 1H NMR (CDCl3): δ1.21 (d, J=8.75 mHz, 6H), 1.35 (m, 2H), 1.51 (m, 2H), 2.50 (s, 3H), 3.71 (m, 3H), 4.93 (b, 1H), 7.18 (m, 6H), 7.32 (m, 2H), 7.46 (m, 6H). 13C NMR (CDCl3): 813.7, 21.1, 25.2, 30.3, 36.7, 43.7, 47.5, 116.5, 116.650, 124.132, 124.325, 125.943, 126.520, 128.027, 128.347, 128.509, 129.018, 131.101, 131.796, 134.8, 136.4, 138.6, 144.1, 153.0, 153.7, 155.6. Anal. Calcd. for C30H32FN3O20.42 H2O: C, 73.06; H, 6.71; N, 8.52. Found: C, 73.24; H, 6.82; N, 8.29. Mass Spec: 486.27 (MH+).

1. waitat 108° C. for 90 minutes
2. additionwas added
3. stirringThe reaction mixture was let stirred at room temperature for 30 minutes
4. waitat 100° C. for 18 hrs
5. customconsumption of starting material
6. temperatureThe reaction was let cooled to room temperature
7. customwhere the solvent was removed by rotorvap
8. customThe crude material was purified by flash column chromatography
9. customProduct was obtained (110 mg, 71%)