Pyridine → Phenylacetyl 7-aminodesacetoxycephalosporanic acid

HRID 1833895Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1833895
[CH3:1][C:2]1([CH3:24])[CH:6]([C:7]([OH:9])=[O:8])[N:5]2[C:10](=[O:22])[C@@H:11]([NH:12][C:13](=[O:21])[CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C@H:4]2[S@:3]1=O.ClC(Cl)(Cl)COP([O-])([O-])=O.N1C=CC=CC=1>O1CCOCC1>[CH3:1][C:2]1[CH2:24][S:3][C@@H:4]2[C@H:11]([NH:12][C:13](=[O:21])[CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:10](=[O:22])[N:5]2[C:6]=1[C:7]([OH:9])=[O:8]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 22764074HCID 22764074, VerbindungHCID 90473365HCID 90473365, Verbindung

Produkt 1

HCID 168674Phenylacetyl 7-aminodesacetoxycephalosporanic acidAusbeute 244,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

The polymer ester of (1S, 5R, 6R)-2,2-dimethyl-6-phenylacetamidopenam-3-carboxylic acid 1-oxide[45.60g, 0.05 mole, from example 29(a)] was refluxed for 24 hours in dioxan (500 ml.) with trichloroethylphosphate (1.15g, 5.0 m.mole) and pyridine (0.41 ml., 0.40g, 0.0051 mole) as in example 16 above to give the polymer ester of (6R, 7R)-3-methyl-7-phenylacetamidoceph-3-em-4-carboxylic acid (40.65g). The IR and NMR spectra were identical with the product obtained in example 8 above.

Quellen und Nachweise

ORD-Eintrag
ord-337e2731ce2340cb8933ead5b57a84b1
Quelldatensatz
uspto-grants-1978_01
Patentnummer
US04067858

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