Ethanol → HCID 86741296, Verbindung

HRID 235774

Reaktionsgleichung

Reaktionsgleichung von HRID 235774
[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[O: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[O: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 3

HCID 702EthanolHCID 24450Potassium Phosphate, DibasicHCID 86741295HCID 86741295, Verbindung

Produkt 1

HCID 86741296HCID 86741296, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11139377Platinum dioxide monohydrateKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 4-nitrobenzyl (5R, 6R)-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-3-(5-methyl-1,3,4-oxadiazol-2-ylthio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (50 mg), platinum (IV) oxide monohydrate (50 mg), ethanol (0.5 ml) and 0.1M aqueous solution of dipotassium hydrogen phosphate (2.35 ml) in a mixture of water (2.5 ml) and dioxane (6 ml) was shaken under a hydrogen atmosphere (40 psi) at ambient temperature for an hour. After the catalyst was filtered off, the filtrate was evaporated to half of the original volume. The resultant aqueous solution was washed three times with diethyl ether and then evaporated in vacuo. The residue was dissolved in water (25 ml) and the resultant aqueous solution was chromatographed on nonionic adsorption resin "Diaion HP-20AG" eluting with water (100 ml) and 10% aqueous isopropyl alcohol (100 ml). The fractions, whose UV spectra showed λmax 292 nm, were combined and lyophilized to give potassium (5R, 6R)-6-(1-hydroxy-1-methylethyl)-3-(5-methyl-1,3,4-oxadiazol-2-ylthio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (14.3 mg) as powder.

Aufarbeitung

  1. filtrationAfter the catalyst was filtered off
  2. customthe filtrate was evaporated to half of the original volume
  3. washThe resultant aqueous solution was washed three times with diethyl ether
  4. customevaporated in vacuo
  5. dissolutionThe residue was dissolved in water (25 ml)
  6. customthe resultant aqueous solution was chromatographed on nonionic adsorption resin "Diaion
  7. wash" eluting with water (100 ml) and 10% aqueous isopropyl alcohol (100 ml)

Quellen und Nachweise

ORD-Eintrag
ord-1b0345dccce4453b9ff1c5dfb0fe1ba1
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04640915

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