Hydrochloric Acid → HCID 58595093, 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 (162 mg, 0.36 mmol) (obtained as described in Example 3) in a mixture of water (1-ml) and tetrahydrofuran (1 ml) was added 1 M hydrochloric acid (0.33 ml, 0.36 mmol) at 0° C. The mixture was concentrated under reduced pressure. To a solution of the residue in acetonitrile (10 ml) were added phenol (102 mg, 1.1 mmol), dimethylaminopyridine (22 mg, 0.18 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (139 mg, 0.73 mmol) at room temperature. After stirring the mixture for 30 minutes, further 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (139 mg, 0.73 mmol) was added thereto and the resulting mixture was stirred for 30 minutes. At the end of this time, to the reaction mixture was added ethyl acetate and the organic layer was washed sequentially with dilute hydrochloric acid, 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 afford phenyl (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 (66 mg, yield 36%) as a colorless powder.

Provenance & Evidence