反应详情

N-Methoxy-N-methyl-3-{2-[2-(2-triisopropylsilanyloxy-naphthalen-1-yl)-ethoxy]-benzenesulfonylamino}-succinamic acid tert-butyl ester (270 mg, 0.38 mmol) was stirred with TBAF (0.45 mL of 1.0 M soln in THF, 0.45 mmol) in freshly distilled THF (1.45 mL) at 0° C. for fifteen minutes and then at room temperature for 1.5 h. The reaction mix was diluted with saturated aq. NH4Cl and was extracted three times with EtOAc. The organic extracts were combined, washed with brine solution, dried over Na2SO4, filtered through celite, and concentrated. The crude product was purified by flash chromatography (SiO2, 50% EtOAc-hexanes) to give 3-{2-[2-(2-hydroxy-naphthalen-1-yl)-ethoxy]-benzenesulfonylamino}-N-methoxy-N-methyl-succinamic acid tert-butyl ester in quantitative yield. MS (APCI) m/z 557.3 (M−1).

1. additionThe reaction mix
2. extractionwas extracted three times with EtOAc
3. washwashed with brine solution
4. dry with materialdried over Na2SO4
5. filtrationfiltered through celite
6. concentrationconcentrated
7. customThe crude product was purified by flash chromatography (SiO2, 50% EtOAc-hexanes)