تفاعل #322945

معادلة التفاعل

sodium phosphate

sodium phosphate

4-nitrobenzyl(5R,6R)-3-(4-pyridylthio)-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

sodium bicarbonate

→

sodium (5R,6R)-3-(4-pyridylthio)-6-(1-hydroxy-1-methylethyl)-7-oxo-1-azabicyclo[3.2.0]-hept-2-ene-2-carboxylate

المذيبات

dioxane

dioxane

ظروف التفاعل

المعالجة

1. 1
   أخرىrose to ambient temperature
2. 2
   ترشيحthe mixture was filtered through cellulose powder
3. 3
   غسيلThe filter-cake was washed with water (3×10 ml)
4. 4
   تركيزThe combined filtrates were concentrated to half of the original volume
5. 5
   غسيلThe concentrate was washed with ethyl acetate (3×20 ml)
6. 6
   أخرىevaporated in vacuo
7. 7
   workup.DISSOLUTIONThe residue was dissolve in water (60 ml)
8. 8
   workup.ADDITIONcontaining sodium chloride (1.75 g)
9. 9
   أخرىchromatographed on nonionic adsorption resin "Diaion HP-20" (Trade Mark, maker
10. 10
    غسيل(1.5×20 cm) eluting with water (100 ml)
11. 11
    workup.ADDITIONa mixture of water and acetone (10:0 to 7:3, 200 ml)
12. 12
    أخرىwere collected

الإجراء التجريبي

A mixture of 5% palladium on activated charcoal (50 ml), dioxane (3.5 ml) and 1/30M sodium phosphate buffer solution (pH 7.0, 1.5 ml) was shaken for an hour under hydrogen atmosphere (40 psi) at ambient temperature. To this mixture was added a solution of 4-nitrobenzyl(5R,6R)-3-(4-pyridylthio)-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (43 mg) in a mixture of dioxane (3.5 ml) and 1/30M sodium phosphate buffer solution (pH 7.0, 1.5 ml) at 0° C., and the resultant mixture was shaken under hydrogen atmosphere (40 psi) for 100 minutes, during which time the reaction temperature rose to ambient temperature. After addition of 1% aqueous sodium bicarbonate (0.57 ml) at 0° C., the mixture was filtered through cellulose powder. The filter-cake was washed with water (3×10 ml). The combined filtrates were concentrated to half of the original volume. The concentrate was washed with ethyl acetate (3×20 ml) and evaporated in vacuo. The residue was dissolve in water (60 ml) containing sodium chloride (1.75 g) and then chromatographed on nonionic adsorption resin "Diaion HP-20" (Trade Mark, maker: Mitsubishi Chemical Industries Ltd. (1.5×20 cm) eluting with water (100 ml) and a mixture of water and acetone (10:0 to 7:3, 200 ml). The fractions, whose UV spectra showed λmax 302 nm, were collected and lyophilized to give sodium (5R,6R)-3-(4-pyridylthio)-6-(1-hydroxy-1-methylethyl)-7-oxo-1-azabicyclo[3.2.0]-hept-2-ene-2-carboxylate (13.7 mg) as white powder.

المصدر