Sodium Hydroxide → HCID 15117447, compound

Participants

Reaction Steps

To a solution of (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(3S)-pyrrolidin-3-yl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (1.0 g) in water (30 ml) was added ethyl acetimidate hydrochloride (2.8 g) at 0° C while adjusting pH to 8.5 with 30% sodium hydroxide solution. After stirring for 30 minutes at the same temperature, the solution was adjusted to pH 6.5 with lN-hydrochloric.acid, washed with ethyl acetate, and then concentrated in vacuo. The residue was chromatographed on nonionic adsorption resin "Diaion HP-20" eluting with aqueous isopropyl alcohol (3%). The farctions containing the desired compound were collected and lyophilized to give (5R,6S)-3-[(3S)-1-acetimidoylpyrrolidin-3-yl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (550 mg).

Provenance & Evidence