Diethyl Ether → HCID 58595175, compound

Participants

Reaction Steps

To a solution of (1R,5S,6S)-2-[1-(4-carbamoyl-1,3-thiazol-2-yl)azetidin-3-yl]thio-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid sodium salt (357 mg, 0.80 mmol) (obtained as described in Example 3) in dimethylformamide (5 ml) was added ethyl iodide (357 mg, 2.40 mmol) at 0° C. under an atmosphere of nitrogen and the mixture was stirred for 1 hour. The mixture was further stirred for 2 hours while gradually raising the temperature to room temperature. At the end of this time, to the reaction mixture was added ethyl acetate and the organic layer was washed sequentially with 10% aqueous sodium chloride solution, 10% aqueous sodium thiosulfate solution saturated aqueous sodium hydrogencarbonate solution, and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using ethyl acetate—20% acetonitrile; ethyl acetate—40% acetonitrile; ethyl acetate—60% acetonitrile and ethyl acetate to give a purified product, which was dissolved in methylene chloride and diethyl ether and hexane were sequentially added to the solution to afford ethyl (1R,5S,6S)-2-[1-(4-carbamoyl-1,3-thiazol-2-yl)azetidin-3-yl]thio-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate (387 mg, yield 95%) as a colorless powder.

Provenance & Evidence