Acetyl chloride → HCID 11604245, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 225 mg (0.61 mmol) 5-3 in 10 mL of pyridine was added 45 μL (0.92 mmol) hydrazine hydrate and the reaction was heated for 1 h at 90° C. After cooling to room temperature, and then to 0° C., 220 μL (3.05 mmol) of acetyl chloride was added, the cooling bath was removed, and the reaction was stirred at room temperature overnight. The reaction was dumped into a separatory funnel containing EtOAc and brine, the layers were separated, the organic phase was washed again with brine, dried over Na2SO4, and concentrated. The residue was then resuspended twice in toluene and concentrated to azeotrope off any remaining pyridine, and then purified by silica gel chromatography with EtOAc/hexanes to provide 5-4 as a mixture of diastereomers. These were again purified on silica gel with a careful gradient of EtOAc/hexanes to provide the individual isomers, each as an off-white solid. Data for the first diastereomer of 5-4 to elute from silica: LC-MS: rt=2.67 min, m/z=425 (M+1). Data for the second diastereomer of 5-4 to elute from silica: LC-MS: rt=2.63 min, m/z=425 (M+1).

Provenance & Evidence