Triphenylphosphine → (S)-N-methoxy-N-methyl-3-[2-(2-quinolin-5-yl-ethoxy)benzenesulfonylamino]-succinamic acid tert-butyl ester

Participants

Reaction Steps

To a solution of S)-3-(2-hydroxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester (2.0 g, 5.15 mmol), quinoline ethanol (0.892 g, 5.15 mmol) and triphenylphospine (2.02 g, 7.73 mmol) in 80 mL of THF at 0° C. was slowly added DEAD (1.22 mL, 7.73 mmol). The reaction was stirred for 17 h with slow warming to RT before removing the solvent. The residue was chromatographed (250 g SiO2-50% EtOAC/Hex) to afford 3.55 g of (S)—N-methoxy-N-methyl-3-[2-(2-quinolin-5-yl-ethoxy)benzenesulfonylamino]-succinamic acid tert-butyl ester (contaminated with some triphenylphosphine oxide). 1H NMR (400 MHz, CDCl3) 8.90(d, 1H, J=4 Hz), 8.61(d, 1H, J=8 Hz), 8.04(d, 1H, J=8 Hz), 7.81(d, 1H, J=8 Hz), 7.69(t, 1H, J=8 Hz), 7.65(t, 1H, J=8 Hz), 7.51(t, 1H, J=8 Hz), 7.49(d, 1H, J=8 Hz), 6.95(t, 1H, J=8 Hz), 6.85(d, 1H, J=8 Hz), 5.90(d, 1H, J=10 Hz), 4.38(m, 1H), 3.90-3.65(m, 2H), 3.45(s, 3H), 2.80(s, 3H), 2.40(ABX, AB portion, 2H, JAB=15, JAX=6, JBX=7, ΔνAB=50.3 Hz), 1.41(s, 9H).

Provenance & Evidence