Pyridine → HCID 86744602, compound

Participants

Reaction Steps

To a mixture of 4.0 g (0.0116 mol) of rac.-(R, R*)-α-hydroxy-4-methoxyphenyl-β-[(2-oxo-2-phenylethyl) thio]benzenepropanamide, 130 mL of methylene chloride and 5 mL of pyridine cooled in an ice-bath was added dropwise a solution of 1.25 g (0.0126 mol) of acetyl chloride in 25 mL of methylene chloride. The mixture was stirred at this temperature for one hour and at room temperature for 17 hours. After dilution with water the aqueous suspension was extracted with methylene chloride. The methylene chloride solution was dried (MgSO4) and removal of the solvent gave a residue which was washed with hexane. The crude product was crystallized from ethyl acetate to give 4.1 g (93%) of rac.-(R,*R*)-α-(acetyloxy)-4-methoxyphenyl-β-[(2-oxo-2-phenylethyl)thio]benzeneprop anamide, mp 154°-155°.

Provenance & Evidence