Triphenylphosphine → N-methoxy-N-methyl-3-{2-[2-(2-triisopropylsilanyloxy-naphthalen-1-yl)-ethoxy]-benzenesulfonylamino}-succinamic acid tert-butyl ester

Participants

Reaction Steps

2-(2-Triisopropylsilanyloxy-naphthalen-1-yl)-ethanol (1.0 g, 2.91 mmol) was mixed with (S)-3-(2-hydroxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester (1.13 g, 2.91 mmol), diethylazodicarboxylate (0.92 mL, 5.8 mmol), and triphenyl phosphine (1.52 g, 5.82 mmol) in THF (18.6 mL) at room temperature for 16 h. The reaction mixture was concentrated onto SiO2 (˜3 g) and then was chromatographed over SiO2 with 20% EtOAc/hexane to give N-methoxy-N-methyl-3-{2-[2-(2-triisopropylsilanyloxy-naphthalen-1-yl)-ethoxy]-benzenesulfonylamino}-succinamic acid tert-butyl ester (1.45 g, 2.03 mmol) as an oil in 69% yield. MS (APCI) m/z 715.4 (M+1).

Provenance & Evidence