Hydrochloric Acid → (4R,5S,6S)-3-[(2S,4S)-2-(2-fluoroethyloxymethyl)-1-formimidoylpyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

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Reaction Steps

To a solution of (4R,5S,6S)-3-[(2S,4S)-2-(2-fluoroethyloxymethyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (0.3 g) in water (90 ml) was added benzyl formimidate hydrochloride (0.4 g) under ice-cooling with stirring, keeping the pH between 8.5-9 with 4N aqueous sodium hydroxide. After stirring for 30 minutes, the mixture was adjusted to pH 6.5 with 1N hydrochloric acid and washed with ethyl acetate (60 ml×3). The aqueous layer was subjected to a column chromatography on nonionic adsorption resin, "Diaion HP-20" (10 ml), washed with water, eluted with a mixture of acetone and water (7:93 V/V), and lyophilized to give (4R,5S,6S)-3-[(2S,4S)-2-(2-fluoroethyloxymethyl)-1-formimidoylpyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid [0.2 g).

Provenance & Evidence