Reaktion #322951

Reaktionsgleichung

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

ethanol

dipotassium hydrogen phosphate

water

→

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

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe catalyst was filtered off
2. 2
   Einengenthe filtrate was concentrated to half of the original volume
3. 3
   EinengenThe aqueous concentrate
4. 4
   Waschenwas washed three times with diethyl ether
5. 5
   Sonstigeevaporated in vacuo
6. 6
   workup.DISSOLUTIONThe residue was dissolved in water (250 ml)
7. 7
   workup.ADDITIONpotassium chloride (12.5 g) was added
8. 8
   SonstigeThe aqueous solution was chromatographed on non-ionic adsorption resin "Diaion HP-20 AG" (3.1×33 cm)
9. 9
   Wascheneluting with water (1 liter) and aqueous isopropyl alcohol (5 to 30%, 1 liter)

Vorschrift

A mixture of 4-nitrobenzyl (5R,6R)-3-(2-aminophenylthio)-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (490 mg) and platinum (IV) oxide monohydrate (200 mg) in a mixture of dioxane (60 ml), ethanol (5 ml), 0.1M aqueous dipotassium hydrogen phosphate (22.7 ml) and water (25 ml) was shaken for 50 minutes under a hydrogen atmosphere (40 psi) at ambient temperature. The catalyst was filtered off and the filtrate was concentrated to half of the original volume. The aqueous concentrate was washed three times with diethyl ether and evaporated in vacuo. The residue was dissolved in water (250 ml), and potassium chloride (12.5 g) was added thereto. The aqueous solution was chromatographed on non-ionic adsorption resin "Diaion HP-20 AG" (3.1×33 cm) eluting with water (1 liter) and aqueous isopropyl alcohol (5 to 30%, 1 liter). The fractions, whose UV spectra showed λ max 303 nm, were combined and lyophilized to give potassium (5R, 6R)-3-(2-aminophenylthio)-6-(1-hydroxy-1-methylethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (130 mg).

Quelle