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HCID 12784140, Verbindung → 7beta-Phenoxyacetamido-3-methoxy-3-cephem-4-carboxylic acid

HRID 465174
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 465174
[N+](C1C=CC(C[O:9][C:10]([C:12]2[N:17]3[C:18](=[O:31])[C@@H:19]([NH:20][C:21](=[O:30])[CH2:22][O:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C@H:16]3[S:15][CH2:14][C:13]=2[O:32][CH3:33])=[O:11])=CC=1)([O-])=O.[H][H]>CO.O1CCCC1.[Pd]>[O:23]([CH2:22][C:21]([NH:20][C@@H:19]1[C:18](=[O:31])[N:17]2[C:12]([C:10]([OH:11])=[O:9])=[C:13]([O:32][CH3:33])[CH2:14][S:15][C@H:16]12)=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 12784140HCID 12784140, VerbindungHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 127841427beta-Phenoxyacetamido-3-methoxy-3-cephem-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 250 mg (0.5 mmol) of 7β-phenoxyacetamido-3-methoxy-3-cephem-4-carboxylic acid p-nitrobenzyl ester in 2 ml of methanol/tetrahydrofuran, 1:1, is added to a mixture of 5% palladium/charcoal in 2 ml of the same solvent, which mixture has been prehydrogenated for one hour under atmospheric pressure, and the reaction mixture is hydrogenated for 3 hours at room temperature and under atmospheric pressure. After this time, about 90% of the calculated amount of hydrogen has been taken up. The catalyst is filtered off and the filtrate is evaporated in vacuo. The residue is taken up in 10 ml of methylene chloride and extracted with twice 10 ml of 5% strength aqueous sodium bicarbonate solution. The combined bicarbonate extracts are neutralised at 0° C. with dilute hydrochloric acid and extracted with 3 times 10 ml of methylene chloride. The organic phase is dried over sodium sulphate and freed from the solvent in vacuo. After crystallisation from chloroform/pentane, the residue gives 7β-phenoxyacetamido-3-methoxy-3-cephem-4-carboxylic acid of melting point 173°-174° C.

Aufarbeitung

  1. waitthe reaction mixture is hydrogenated for 3 hours at room temperature and under atmospheric pressure
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated in vacuo
  4. extractionextracted with twice 10 ml of 5% strength aqueous sodium bicarbonate solution
  5. customare neutralised at 0° C. with dilute hydrochloric acid
  6. extractionextracted with 3 times 10 ml of methylene chloride
  7. dry with materialThe organic phase is dried over sodium sulphate
  8. customAfter crystallisation from chloroform/pentane

Quellen und Nachweise

ORD-Eintrag
ord-ad0bdd55216149d887afd5be3706bf02
Quelldatensatz
uspto-grants-1985_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04550162

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