反应详情

温度

60 °C

A mixture of 2-benzyloxy-4-(tert-butyldimethylsilanyloxy)-phenylamine, t-butyl bromoacetate (3.8 mL, 25.7 mmol), and potassium carbonate (7.1 g, 51.4 mmol) in DMF (20 mL) is heated at 60° C. for 18 h. Additional t-butyl bromoacetate (1 mL) is added and the mixture is stirred and heated for an additional 5 h. The mixture is poured into EtOAc and extracted once with water and four times with brine. The organic phase is dried over magnesium sulfate and the solvent removed under reduced pressure to furnish an oil consisting of product and desilylated product. A solution of this material, t-butyldimethychlorosilane (3.87 g, 25.7 mmol), imidazole (2.33 g, 34.2 mmol), and dimethylaminopyridine (3 mg) in DMF (15 mL) is stirred at RT for 18 h. This solution is poured into EtOAc and extracted with water (1×) and brine (5×). The organic phase is dried over magnesium sulfate and the solvent removed under reduced pressure to afford crude product, which is chromatographed on silica gel to afford the title compound: 1H NMR (CDCl3δ 7.27 (m, 5H), 6.26 (m, 3H), 4.96 (s, 2H), 4.45 (br s, 1H), 3.91 (s, 2H), 1.35 (s, 9H), 0.84 (s, 9H), 0.00 (s, 6H); (M+1)+=444.

1. temperatureheated for an additional 5 h
2. extractionextracted once with water and four times with brine
3. dry with materialThe organic phase is dried over magnesium sulfate
4. customthe solvent removed under reduced pressure
5. customto furnish an oil
6. extractionextracted with water (1×) and brine (5×)
7. dry with materialThe organic phase is dried over magnesium sulfate
8. customthe solvent removed under reduced pressure
9. customto afford crude product, which
10. customis chromatographed on silica gel