Hydrochloric Acid → HCID 54040558, compound

Participants

Reaction Steps

To a solution of (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[(2S,4S)-2-{(2-ureidoethyl)oxymethyl}-pyrrolidin-4-yl]thio-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (0.15 g) in water (30 ml) was added ethyl acetimidate hydrochloride (1.65 g) by portions at 0°-5° C., keeping the pH between 8.4-8.6 with 10% aqueous potassium carbonate. After adjusting to pH 6.5 with lN aqueous hydrochloric acid, the solution was washed with 10% solution of tetrahydrofuran in ethyl acetate (50 ml) by four portions and the organic solvent was removed by evaporation. The residual solution was subjected to a column chromatography on nonionic adsorption resin, "HP-20" (30 ml), washed with water, eluted with 5% aqueous isopropyl alcohol and lyophilized to give (4R,5S,6S)-3-[(2S,4S)-1-acetimidoyl-2-{(2-ureidoethyl)oxymethyl}pyrrolidin-4-yl]thio-6-[ (1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (0.11 g).

Provenance & Evidence