Potassium Carbonate → HCID 140360503, compound

Participants

Reaction Steps

To a solution of (5R,6S)-3-[(1S)-1,2-diaminoethyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (1.00 g) in a mixture of water (100 ml) and tetrahydrofuran (100 ml) was added portionwise ethyl acetimidate hydrochloride (1.00 g) under ice-cooling with stirring, keeping the pH between 8.0 and 8.5 with saturated aqueous potassium carbonate. After stirring for 2 hours, the mixture was concentrated under reduced pressure to be about 10 ml-volume. The aqueous solution was subjected to a column chromatography on silica gel (100 g) and eluted with a mixture of water and acetonitrile (6:4, V/V). The fractions containing the object compound were collected, concentrated under reduced pressure, and lyophilized to give a solid. A solution of the solid in water (10 ml) was subjected to a column chromatography on "Diaion HP-20" and eluted with water. The fractions containing the objected compound were collected, concentrated under reduced pressure, and lyophilized to give (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-[(4S)-2-methyl-2-imidazolin-4-yl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (0.08 g) as a solid.

Provenance & Evidence