Ethyl Acetate → HCID 58595064, 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 (402 mg, 0.90 mmol) (obtained as described in Example 3) in dimethylacetamide (5 ml) was added iodomethyl pivalate (261 mg, 1.08 mmol) at 0° C. under an atmosphere of nitrogen and the mixture was stirred for 1 hour. 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. To the residue was added diethyl ether to afford pivaloyloxymethyl (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 (450 mg, yield 93%) as a colorless powder.

Provenance & Evidence