Acetic Anhydride → Glutaryl-7-aminocephalosporanic acid

HRID 1588330

Reaktionsgleichung

Reaktionsgleichung von HRID 1588330
[CH2:1]1[S:6][C@@H:5]2[C@H:7]([NH:10][C:11]([CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[O:12])[C:8](=[O:9])[N:4]2[C:3]([C:19]([OH:21])=[O:20])=[C:2]1[CH2:22][OH:23].[C:24](OC(=O)C)(=[O:26])[CH3:25].[OH-].[Na+]>>[CH3:25][C:24]([O:23][CH2:22][C:2]1[CH2:1][S:6][C@@H:5]2[C@H:7]([NH:10][C:11]([CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[O:12])[C:8](=[O:9])[N:4]2[C:3]=1[C:19]([OH:21])=[O:20])=[O:26]

Komponenten

4

Edukt 3

HCID 7918Acetic Anhydride2×HCID 14798Sodium HydroxideHCID 6453255(6R,7R)-7-((4-Carboxy-1-oxobutyl)amino)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid

Produkt 1

HCID 446570Glutaryl-7-aminocephalosporanic acidAusbeute 74.000 %

Versuchsvorschrift

To an aqueous solution of desacetyl glutaryl 7ACA (4 ml, 0.20 mmoles) chilled in an ice bath is added 0.4 ml acetic anhydride (4.2 mmoles) dropwise and 20% sodium hydroxide (9.75 mmoles) is pumped in to maintain the reaction pH at 7.0±1. After all of the acetic anhydride is added and the pH stabilizes, by HPLC there is now 0.148 moles of glutaryl 7ACA (yield is 74%). There is 4.5% of desacetyl glutaryl 7ACA remaining along with 10% of a compound tentatively identified as the cyclic glutarimide 7ACA derivative.

Aufarbeitung

  1. temperatureto maintain the reaction pH at 7.0±1

Quellen und Nachweise

ORD-Eintrag
ord-2009c0b86b7d417dade55be0f6878f49
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05221739

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