Ethanol → HCID 86741293, Verbindung

HRID 235769

Reaktionsgleichung

Reaktionsgleichung von HRID 235769
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH2:15][C@H:14]2[N:11]([C:12](=[O:33])[C@H:13]2[C:16]([CH3:32])([O:18]C(OCC2C=CC([N+]([O-])=O)=CC=2)=O)[CH3:17])[C:10]=1[C:34]([O:36]CC1C=CC([N+]([O-])=O)=CC=1)=[O:35].C(O)C.P([O-])([O-])(O)=O.[K+:55].[K+].O>O1CCOCC1.O.[Pt](=O)=O>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH2:15][C@H:14]2[N:11]([C:12](=[O:33])[C@H:13]2[C:16]([OH:18])([CH3:32])[CH3:17])[C:10]=1[C:34]([O-:36])=[O:35].[K+:55]

Komponenten

7

Edukt 4

HCID 702EthanolHCID 962WaterHCID 24450Potassium Phosphate, DibasicHCID 53970580HCID 53970580, Verbindung

Produkt 1

HCID 86741293HCID 86741293, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11139377Platinum dioxide monohydrateKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

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).

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 (250 ml)
  7. additionpotassium chloride (12.5 g) was added
  8. customThe aqueous solution was chromatographed on non-ionic adsorption resin "Diaion HP-20 AG" (3.1×33 cm)
  9. washeluting with water (1 liter) and aqueous isopropyl alcohol (5 to 30%, 1 liter)

Quellen und Nachweise

ORD-Eintrag
ord-e1719374b6824c27b3ae6893bb9dde21
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04640915

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