Phosphate → HCID 86596169, compound

Participants

Reaction Steps

To a solution of 4-nitrobenzyl (5R,6S)-7-oxo-6-{(1R)-1-[(trimethylsilyl)oxy]ethyl}-3-{3-[(trimethylsilyl)oxy]phenyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (207 mg) in acetonitrile (3 ml) was added under ice cooling 0.1N hydrochloric acid (0.3 ml), and the mixture was stirred for 15 minutes. After the solution was neutralized with a 0.1N aqueous sodium hydrogencarbonate solution (0.3 ml), further thereto 0.25M phosphate buffer (10 ml, pH6) and acetonitrile (7 ml) were added. Zinc dust (1.49 g) was added thereto and the mixture was vigorously stirred for an hour under ice cooling and for additional an hour at room temperature. The insoluble materials were removed with celite and washed with water and chloroform. Then, the filtrate and the washed solvent were combined to separate by a separating funnel. The aqueous layer was washed with chloroform, twice separated with a separating funnel and an organic solvent in the aqueous layer was removed under reduced pressure. The aqueous solution was purified by polymer chromatography (CHP-20P), and the fractions eluted with water were collected to be subjected to freeze-drying to give sodium (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-(hydroxyphenyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (14 mg).

Provenance & Evidence