反应详情

A mixture of 5% palladium on activated carbon (175 mg), dioxane (12.5 ml) and 1/30M sodium phosphate buffer (pH 7.0, 5.5 ml) was shaken for an hour under a hydrogen atmosphere (40 psi) at ambient temperature. A solution of 4-nitrobenzyl (5R,6R)-3-(2-acetamidoethylthio)-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (175 mg) in a mixture of dioxane (12 ml) and 1/30M sodium phosphate buffer (pH7.0, 5 ml) was added to the mixture at 0° C. and the resulting mixture was shaken under a hydrogen atmosphere (40 psi) for an hour, during which time the reaction temperature rose to ambient temperature. 1% Aqueous solution of sodium bicarbonate (2.29 ml) was added therein at 0° C. and the mixture was filtered through cellulose powder. The filter-cake was washed with water (3×20 ml). The combined filtrates were concentrated to a half volume, washed with ethyl acetate (3×50 ml), and evaporated in vacuo. The residue was dissolved in water (220 ml) containing sodium chloride (6.6 g) and chromatographed on Diaion non-ionic adsorption resin, HP-20 AG (trade mark, made by Mitsubishi Chemical Industries) (150-300μ, φ2.2×36 cm) eluting with water (360 ml) and a mixture of water and acetone (10:0 to 7:3, 600 ml). The fractions, whose UV spectra showed λmax 300 nm, were combined and lyophilized to give sodium (5R,6R)-3-(2-acetamidoethylthio)-6-(1-hydroxy-1-methylethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (46.5 mg) as white powder.

1. additionwas added to the mixture at 0° C.
2. stirringthe resulting mixture was shaken under a hydrogen atmosphere (40 psi) for an hour
3. customrose to ambient temperature
4. filtrationat 0° C. and the mixture was filtered through cellulose powder
5. washThe filter-cake was washed with water (3×20 ml)
6. concentrationThe combined filtrates were concentrated to a half volume
7. washwashed with ethyl acetate (3×50 ml)
8. customevaporated in vacuo
9. dissolutionThe residue was dissolved in water (220 ml)
10. additioncontaining sodium chloride (6.6 g)
11. customchromatographed on Diaion non-ionic adsorption resin, HP-20 AG (trade mark, made by Mitsubishi Chemical Industries) (150-300μ, φ2.2×36 cm)
12. washeluting with water (360 ml)
13. additiona mixture of water and acetone (10:0 to 7:3, 600 ml)