Phosphorisocyanatidic dichloride → Cefuroxime

HRID 894833

Reaktionsgleichung

Reaktionsgleichung von HRID 894833
ClP([N:5]=[C:6]=[O:7])(Cl)=O.[O:8]1[CH:12]=[CH:11][CH:10]=[C:9]1/[C:13](=[N:31]/[O:32][CH3:33])/[C:14]([NH:16][C@@H:17]1[C:29](=[O:30])[N:19]2[C:20]([C:26]([OH:28])=[O:27])=[C:21]([CH2:24][OH:25])[CH2:22][S:23][C@H:18]12)=[O:15]>CC(C)=O>[CH3:33][O:32]/[N:31]=[C:13](\[C:14]([NH:16][C@@H:17]1[C:29](=[O:30])[N:19]2[C:20]([C:26]([OH:28])=[O:27])=[C:21]([CH2:24][O:25][C:6]([NH2:5])=[O:7])[CH2:22][S:23][C@H:18]12)=[O:15])/[C:9]1[O:8][CH:12]=[CH:11][CH:10]=1

Komponenten

4

Edukt 2

HCID 70090Phosphorisocyanatidic dichlorideHCID 9800056(6R,7R)-7-(((2Z)-2-(2-Furanyl)-2-(methoxyimino)acetyl)amino)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid

Produkt 1

HCID 5479529CefuroximeAusbeute 56,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

The process of Example 3 was repeated, using dichlorophosphinyl isocyanate (1.46 ml) and a solution of (6R,7R)-7-[Z-2-(fur-2-yl)-2-methoxyiminoacetamido]-3hydroxymethylceph-3-em-4-carboxylic acid (3.81 g) in acetone (50 ml) cooled to 4°, but the reaction mixture was heated at 45° for 2 hours and then kept at 20° overnight, to give the title compound (2.40 g, 56.7%); purity by HPLC 95.6% and by TLC 94.5%.

Aufarbeitung

  1. temperaturethe reaction mixture was heated at 45° for 2 hours

Quellen und Nachweise

ORD-Eintrag
ord-1c61885a5b8b4ff480bd40d166cecdaa
Quelldatensatz
uspto-grants-1981_08
Patentnummer
US04284767

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