HCID 12961570, compound → HCID 14782602, compound

Participants

Reaction Steps

54 mg of p-nitrobenzyl 3-(4-pyridylthio)-6-ethyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate obtained in Example 17 was dissolved in a mixture of 2 ml of dioxane and 2 ml of a 0.1 M phosphate buffer (pH 7.0). Then, 54 mg of platinum oxide was added, and the reaction was performed at room temperature for 4 hours in a Paar reducing apparatus (hydrogen pressure 4 kg/cm2). The catalyst was removed by filtration. The filtrate and the wash liquid were combined and concentrated under reduced pressure to about 2/3 of the original amount. To the resulting solution was added 2.5 g of sodium chloride, and further water was added to make the total amount 50 ml. The solution was charged on a column of Diaion HP-20AG (1.1×20 cm), and eluted with 300 ml in total of an aqueous solution of acetone having a concentration gradually varying from 0 to 30% by a concentration gradient method. The eluate was fractionated into 5 g fractions. The fractions were screened by high-velocity liquid chromatography, and fractions having an ultraviolet absorption at λmax 303 nm were collected, and lyophilized to afford 20.7 mg (yield 56.8%) of the captioned product.

Provenance & Evidence