Sulfuryl chloride → HCID 86741247, compound

Participants

Reaction Steps

Sulphuryl chloride (59.7 mg, 35.8 μl, 0.442 mmole) was added to a solution of methyl 2-(4-methylthio-2-azetidinon-1-yl)-2-(4-trifluoromethyl-4-hydroxy-1,3-dithiolan-2-ylidene)acetate (166 mg, 0.442 mmole) in methylene chloride (3 ml) at room temperature, with stirring. After this addition, the solution was stirred for 3 minutes and then the solvent was distilled off to give the crude methyl 2-(4-chloro-2-azetidinon-1-yl)-2-(4-trifluoromethyl-4-hydroxy-1,3-dithiolan-2-ylidene)acetate. This 4-chloroazetidinone compound was dissolved in methylene chloride (3 ml) without purification, and triethylamine (185 μl) was added thereto, after which the mixture was stirred at room temperature for 2 hours. The solvent was distilled off from the reaction mixture under reduced pressure. The resulting residue was dissolved in ethyl acetate and washed with an aqueous solution of sodium chloride and dried over anhydrous sodium sulphate. The solvent was distilled off under reduced pressure and the residue was purified by preparative thin layer chromatography (eluent: a 3:2 by volume mixture of benzene and ethyl acetate), to give 63 mg of the desired product as crystals.

Provenance & Evidence