Toluene → Methyl 3-[4-(2-t-butoxycarbonylamino-phenylcarbamoyl)-phenyl]-acrylate

Participants

Reaction Conditions

Reaction Steps

A stirred suspension of compound XI (500 mg, 1.47 mmol), methyl (triphenyl-phosphoranylidene)acetate (590 mg, 1.76 mmol) in anhydrous toluene (20 ml) was heated at 90° C. under nitrogen. After 2 days, the reaction mixture was concentrated and directly purified by flash chromatography on silica gel (AcOEt/hexane:30/70→40/60) to afford the title compound XII (568 mg, 1.43 mmol, 97% yield) as a pale yellow foam. 1H NMR (300 MHz, CDCl3) δ(ppm): 9.32 (bs, 1H), AB system (δA=7.99, δB=7.62, J=8.4 Hz, 4H), 7.87 (d, J=7.9 Hz, 1H), 7.73 (s, J=15.8 Hz, 1H), 7.32–7.13 (m, 3H), 6.69 (bs, 1H), 6.53 (d, J=16.3 Hz, 1H), 3.83 (s, 3H), 1.53 (s, 9H).

Provenance & Evidence