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0 °C

A solution of (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-(pyrrolidin-3-yl)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (180 mg) in phosphate buffer solution (pH was adjusted to around pH 8.5 with 30% aqueous potassium carbonate at 0° C. To the solution was added four portions of ethyl acetimidate hydrochloride (835 mg), while adjusting pH to around 8.5 with j0% aqueous potassium carbonate. After stirring for 10 minutes at 0° C., the solution was adjusted to around pH 7.0 with 1N hydrochloric acid. After the mixture was washed with a mixture of ethyl acetate (270 ml) and tetrahydrofuran (30 ml), the aqueous layer was concentrated. The resulting solution was chromatographed on nonionic adsorption resin "Diaion HP-20" (40 ml) eluting with a mixture of acetonitrile and water (2:98, V/V). The fractions containing the object compound were collected and freeze-dried to give (5R,6S)-3-(1-acetimidoylpyrrolidin-3-yl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (80 mg).

1. washAfter the mixture was washed with a mixture of ethyl acetate (270 ml) and tetrahydrofuran (30 ml)
2. concentrationthe aqueous layer was concentrated
3. customThe resulting solution was chromatographed on nonionic adsorption resin "Diaion
4. wash" (40 ml) eluting with a mixture of acetonitrile and water (2:98, V/V)
5. additionThe fractions containing the object compound
6. customwere collected
7. customfreeze-dried