Ethanol → potassium (5R,6R)-6-(1-hydroxy-1-methylethyl)-3-(1-methyl-1H-tetrazol-5-ylthio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

HRID 235767

Reaktionsgleichung

Reaktionsgleichung von HRID 235767
[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[N:44]([CH3:45])[N:43]=[N:42][N:41]=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[N:44]([CH3:45])[N:43]=[N:42][N:41]=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 867412914-nitrobenzyl (5R,6R)-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-3-(1-methyl-1H-tetrazol-5-ylthio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Produkt 1

HCID 86741292potassium (5R,6R)-6-(1-hydroxy-1-methylethyl)-3-(1-methyl-1H-tetrazol-5-ylthio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

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-(1-methyl-1H-tetrazol-5-ylthio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (50 mg) and platinum (IV) oxide monohydrate (25 mg) in a mixture of dioxane (10 ml), ethanol (0.5 ml), 0.1M aqueous dipotassium hydrogen phosphate (2.35 ml) and water (3.5 ml) was shaken for an hour 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 thereto. The aqueous solution was chromatographed on non-ionic adsorption resin "Diaion HP-20 AG" (1.35×17.5 cm), eluting with water (100 ml) and 10% aqueous isopropyl alcohol (100 ml). The fractions, whose UV spectra showed λmax 289 nm, were combined and lyophilized to give potassium (5R,6R)-6-(1-hydroxy-1-methylethyl)-3-(1-methyl-1H-tetrazol-5-ylthio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (17 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" (1.35×17.5 cm)
  9. washeluting with water (100 ml) and 10% aqueous isopropyl alcohol (100 ml)

Quellen und Nachweise

ORD-Eintrag
ord-bc39318e70384a0c8e0c0f336d08e311
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04640915

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