Water → HCID 70464043, Verbindung

HRID 543544

Reaktionsgleichung

Reaktionsgleichung von HRID 543544
CC(O[CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=O.O.[CH3:20][N:21]([CH3:31])[C:22]([CH2:24][C:25]1[S:26][C:27]([SH:30])=[N:28][N:29]=1)=[O:23].P(Cl)(Cl)(OP(Cl)(Cl)=O)=O>C(#N)C>[NH2:13][CH:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH2:5][S:30][C:27]3[S:26][C:25]([CH2:24][C:22]([N:21]([CH3:20])[CH3:31])=[O:23])=[N:29][N:28]=3)[CH2:15][S:14][C@H:9]12

Komponenten

6

Edukt 4

HCID 962WaterHCID 4413287-Aminocephalosporanic acidHCID 4432411Diphosphoryl tetrachlorideHCID 178484515HCID 178484515, Verbindung

Produkt 1

HCID 70464043HCID 70464043, VerbindungAusbeute 87,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

Mixed were 1.36 g of 7-ACA, 0.36 g of water and 1.32 g of 2-dimethylaminocarbonylmethyl-5-mercapto-1,3,4-thiadiazole, and 6.5 ml of acetonitrile was added. 5.04 g of diphosphoryl tetrachloride was added through a dropping funnel to the mixture at -20° to -30° C., followed by rinsing the funnel with 1.5 ml of acetonitrile. The reaction mixture was warmed at 10° C. over a period of 5 minutes with stirring, placed in a warm water bath of 40° C. and stirred at the same temperature for 20 minutes. The reaction solution was cooled with ice and adjusted to pH 4.1 with aqueous concentrated ammonia after the addition of 10 ml of cold water. The precipitate was recovered by filtration, washed with water and dried, thereby affording 1.82 g (87.6%) of 7-amino-3-(2-dimethylaminocarbonylmethyl-1,3,4-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid.

Aufarbeitung

  1. additionMixed
  2. additionwas added
  3. washby rinsing the funnel with 1.5 ml of acetonitrile
  4. customplaced in a warm water bath of 40° C.
  5. stirringstirred at the same temperature for 20 minutes
  6. temperatureThe reaction solution was cooled with ice
  7. additionafter the addition of 10 ml of cold water
  8. filtrationThe precipitate was recovered by filtration
  9. washwashed with water
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d0bc62e7a509467b8b3f405fab019620
Quelldatensatz
uspto-grants-1984_05
Patentnummer
US04446318

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