Ethanol → HCID 86741290, Verbindung

HRID 235765

Reaktionsgleichung

Reaktionsgleichung von HRID 235765
[CH3:1][C:2]([C@@H:18]1[C:24](=[O:25])[N:23]2[C@@H:19]1[CH2:20][C:21]([S:39][C:40]1[S:41][C:42]([CH3:45])=[N:43][N:44]=1)=[C:22]2[C:26]([O:28]CC1C=CC([N+]([O-])=O)=CC=1)=[O:27])([O:4]C(OCC1C=CC([N+]([O-])=O)=CC=1)=O)[CH3:3].C(O)C.P([O-])([O-])(O)=O.[K+:54].[K+].O>O1CCOCC1.O.[Pt](=O)=O>[OH:4][C:2]([C@@H:18]1[C:24](=[O:25])[N:23]2[C@@H:19]1[CH2:20][C:21]([S:39][C:40]1[S:41][C:42]([CH3:45])=[N:43][N:44]=1)=[C:22]2[C:26]([O-:28])=[O:27])([CH3:3])[CH3:1].[K+:54]

Komponenten

7

Edukt 4

HCID 702EthanolHCID 962WaterHCID 24450Potassium Phosphate, DibasicHCID 54564139HCID 54564139, Verbindung

Produkt 1

HCID 86741290HCID 86741290, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11139377Platinum dioxide monohydrateKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 4-nitrobenzyl (5R,6R)-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-3-(5-methyl-1,3,4-thiadiazol-2-ylthio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (50 mg) and platinum (IV) oxide monohydrate (50 mg) in a mixture of dioxane (6 ml), ethanol (0.5 ml), 0.1M aqueous dipotassium hydrogen phosphate (2.28 ml) and water (2.5 ml) was shaken for 1.5 hours 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 (25 ml) and potassium chloride (1.25 g) was added. The aqueous solution was chromatographed on non-ionic adsorption resin, "Diaion HP-20 AG" (Trademark, manufactured by Mitsubishi Chemical Industries Ltd.) (1.2×22 cm), eluting with water (150 ml) and aqueous isopropyl alcohol (5 to 30%, 100 ml). The fractions, whose UV spectra showed λmax 293 nm, were combined and lyophilized to give potassium (5R,6R)-6-(1-hydroxy-1-methylethyl)-3-(5-methyl-1,3,4-thiadiazol-2-ylthio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (16.9 mg).

Aufarbeitung

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated to half of the original volume
  3. concentrationThe aqueous concentrate
  4. washwas washed three times with diethyl ether
  5. customevaporated in vacuo
  6. dissolutionThe residue was dissolved in water (25 ml)
  7. additionpotassium chloride (1.25 g) was added
  8. customThe aqueous solution was chromatographed on non-ionic adsorption resin, "Diaion HP-20 AG" (Trademark, manufactured by Mitsubishi Chemical Industries Ltd.) (1.2×22 cm)
  9. washeluting with water (150 ml) and aqueous isopropyl alcohol (5 to 30%, 100 ml)

Quellen und Nachweise

ORD-Eintrag
ord-3d56997817514848b63032c24278a152
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04640915

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