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Hydrochloric Acid → Cefuroxime

HRID 894832
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 894832
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].C([O-])(O)=O.[Na+].Cl.[OH-].[Na+]>C(#N)C.O.C(O)(=O)C.CO.C(Cl)(Cl)Cl>[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
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Komponenten

11

Edukt 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70090Phosphorisocyanatidic dichlorideHCID 516892Sodium BicarbonateHCID 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 5479529
Cefuroxime
Ausbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Dichlorophosphinyl isocyanate (1.46 ml) was added to a stirred suspension of (6R,7R)-7-[Z-2-(fur-2-yl)-2-methoxyiminoacetamido]-3-hydroxymethylceph-3-em-4-carboxylic acid (3.81 g) in acetonitrile (50 ml) cooled to 5°. The reaction mixture was stirred at 5° for 15 minutes and then added to a solution of NaHCO3 (5.1 g) in water (100 ml). This mixture was stirred for 10 minutes when the pH was adjusted from 7.4 to 5.0 with hydrochloric acid. The pH fell to 3.0 after a further 10 minutes so it was readjusted to 5.0 with aqueous sodium hydroxide solution. The mixture was kept at ca. 20° overnight and then heated at 45° for 2 hours when TLC (chloroform:methanol:acetic acid=9:2:1) showed that reaction was essentially complete. The precipitated white solid was removed by filtration and the filtrate was washed with ethyl acetate. The aqueous phase was acidified to pH 1.9 with dilute hydrochloric acid in the presence of ethyl acetate. The aqueous phase was re-extracted with ethyl acetate, and the combined ethyl acetate extracts were washed with 25% aqueous sodium chloride solution and then evaporated. The solid residue was triturated with diethyl ether to give the title compound (3.18 g, 75.0%), purity by HPLC 95.4% and by TLC 91%.

Aufarbeitung

  1. temperaturecooled to 5°
  2. stirringThis mixture was stirred for 10 minutes when the pH
  3. waitThe pH fell to 3.0 after a further 10 minutes so it
  4. waitThe mixture was kept at ca. 20° overnight
  5. customshowed that reaction
  6. customThe precipitated white solid was removed by filtration
  7. washthe filtrate was washed with ethyl acetate
  8. extractionThe aqueous phase was re-extracted with ethyl acetate
  9. washthe combined ethyl acetate extracts were washed with 25% aqueous sodium chloride solution
  10. customevaporated
  11. customThe solid residue was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-1cad6ea37adf4ef9b6d06601bb629461
Quelldatensatz
uspto-grants-1981_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04284767

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