Hydrochloric Acid → HCID 66615893, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of (benzyloxycarbonylmethyl)-triphenylphosphionium bromide (315 mg, 0.642 mmol) in THF (6 mL) at 0° C. is added NaH (60% in mineral oil, 27 mg, 0.642 mmol) and the suspension is allowed to stir at 0° C. for 30 min. (4-{4-[2-(3-Chlorophenylamino)-oxazol-5-yl]-phenyl}-cyclohexyl)-acetaldehyde (253 mg, 0.642 mmol) in THF (4 mL) is added dropwise. The reaction mixture is then stirred a 0° C. for 30 min and the at ambient temperature for 18 h. Water (10 mL) and HCl solution (1N, 15 mL) is added, and the reaction mixture is extracted with EtOAc (3×15 mL). The organic phase is washed with water (1×5 mL), brine (3×20 mL), dried and concentrated to give the title compound (279 mg) as an off-white solid: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.02-1.14 (m, 2H) 1.34-1.49 (m, 3H) 1.59-1.73 (m, 1H) 1.80-1.87 (m, 3H) 2.11 (t, J=8.00 Hz, 2H) 2.46 (ddd, J=11.68, 9.16, 2.91 Hz, 1H) 5.11 (s, 2H) 5.82 (d, J=15.66 Hz, 1H) 6.90-6.99 (m, 1H) 7.14-7.17 (d, 8.08 Hz, 2H) 7.24-7.28 (m, 3H) 7.28-7.32 (m, 6H) 7.40 (d, J=8.08 Hz, 1H) 7.49 (s, 1H); (M+H)+527.2.

Provenance & Evidence