反应详情

To the solution of (S)-Methyl 5-(S-phenylsulfonimidoyl)pentanoate (475 mg, 1.86 mmol) in anhydrous DMF (6 mL) at room temperature under nitrogen atmosphere was added diisopropylethylamine (0.65 μL), 5-bromonicotinic acid (0.38 g), and (benzotriazol-1-yloxy)-tris(dimethylamino)-phosphonium hexafluorophosphate (0.81 g). The resulting reaction mixture was stirred for about 15 min at room temperature and then poured into saturated aqueous NaHCO3. The aqueous was extracted with EtOAc (1×), which was then washed with saturated aqueous NaHCO3 and brine (v:v 1:1, 2×), brine (1×), and dried with anhydrous sodium sulfate. The solution was decanted and concentrated with silica gel. A column chromatography (EtOAc-Hex 1:2) rendered the title compound as slightly yellow colored solid in amount of (616 mg, 75%).

1. customThe resulting reaction mixture
2. extractionThe aqueous was extracted with EtOAc (1×), which
3. washwas then washed with saturated aqueous NaHCO3 and brine (v:v 1:1, 2×), brine (1×)
4. dry with materialdried with anhydrous sodium sulfate
5. customThe solution was decanted
6. concentrationconcentrated with silica gel