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Sodium Iodide → HCID 14535682, Verbindung

HRID 1905013
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1905013
[I-].[Na+].[Cl:3][C:4]([Cl:51])([Cl:50])[CH2:5][O:6][C:7]([NH:9][C@@H:10]1[C:48](=[O:49])[N:12]2[C:13]([C:32]([O:34][CH:35]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[O:33])=[C:14](OP(C3C=CC=CC=3)(C3C=CC=CC=3)=O)[CH2:15][S:16][C@H:11]12)=[O:8]>C(#N)C.[Ag].C(NC(/C=C\S)=O)C>[Cl:50][C:4]([Cl:51])([Cl:3])[CH2:5][O:6][C:7]([NH:9][C@@H:10]1[C:48](=[O:49])[N:12]2[C:13]([C:32]([O:34][CH:35]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)=[O:33])=[C:14]([S:16]/[CH:11]=[CH:10]\[C:48](=[O:49])[NH:12][CH2:13][CH3:14])[CH2:15][S:16][C@H:11]12)=[O:8]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 5238Sodium IodideHCID 14535680HCID 14535680, Verbindung

Produkt 1

HCID 14535682HCID 14535682, VerbindungAusbeute 186,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 88619285HCID 88619285, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

(a') To a suspension of 784 mg (3.294 mM) of (Z)-2-(N-ethylcarbamoyl)vinylmercaptan silver salt in 30 ml of acetonitrile was added 2.965 g (19.77 mM) of sodium iodide, and the mixture was stirred at room temperature for 5 minutes. To the mixture was added at 0° C. a solution of 2 g (2.53 mM) of benzhydryl 7β-2,2,2-trichloroethoxycarbonylamino-3-diphenylphosphoryloxy-3-cephem-4-carboxylate in 20 ml of acetonitrile, and the mixture was stirred at the same temperature for 30 minutes, and then some insoluble material was filtered. To the filtrate was added 100 ml of ethyl acetate, and the mixture was washed with a saturated aqueous sodium chloride solution (50 ml×3) and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was chromatographed over silica gel column (eluent; chloroform) to give 1.65 g of benzhydryl 7β-2,2,2-trichloroethyoxycarbonylamino-3-[(Z)-2-(N-ethylcarbamoyl)vinylthio]-3-cephem-4-carboxylate.

Aufarbeitung

  1. stirringthe mixture was stirred at the same temperature for 30 minutes
  2. filtrationsome insoluble material was filtered
  3. additionTo the filtrate was added 100 ml of ethyl acetate
  4. washthe mixture was washed with a saturated aqueous sodium chloride solution (50 ml×3)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was chromatographed over silica gel column (eluent; chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-3e5a81b7764646f68ffe9266381da832
Quelldatensatz
uspto-grants-1989_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04841044

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