Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 58467989, compound

Participants

Reaction Steps

A mixture of (carbethoxymethylene)triphenylphosphorane (0.214 g, 0.614 mmol) and tert-butyl (5S,6S)-6-(2,3-difluorophenyl)-9-oxo-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ylcarbamate (0.199 g, 0.512 mmol) in toluene (5 mL) was heat to reflux for 18 h. The solvent was removed via vacuum and the crude residue was loaded onto a silica gel column directly. Purification was performed by elution with ethyl acetate in hexane from 0 to 65% to afford the desired product (138 mg, 59%): MS(ESI)[M+H+]=459.22; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.53 (1H, dd, J=4.8, 1.3 Hz), 7.70 (1H, d, J=7.5 Hz), 7.32 (1H, dd, J=7.8, 4.8 Hz), 7.15-7.24 (1H, m), 7.05-7.13 (2H, m), 6.39 (1H, t, J=2.3 Hz), 5.21-5.31 (1H, m), 4.89-4.99 (1H, m), 4.19 (2H, q, J=7.1 Hz), 3.32-3.43 (1H, m), 3.17-3.32 (1H, m), 3.12 (1H, d, J=2.3 Hz), 1.87 (2H, d, J=4.5 Hz), 1.14-1.38 (13H, m).

Provenance & Evidence