Ammonia → 7-Amino-3-(4,6-diamino-1-methyl-pyrimidinium-2-yl)thiomethyl-3-cephem-4-carboxylate

HRID 847423Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 847423
C(O[CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH2:17])[C:15](=[O:18])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=O)C.[NH2:19][C:20]1[CH:25]=[C:24]([NH2:26])[N:23]([CH3:27])[C:22](=[S:28])[N:21]=1.CO.N>C(#N)C>[NH2:17][CH:16]1[C:15](=[O:18])[N:10]2[C:11]([C:12]([O-:14])=[O:13])=[C:6]([CH2:5][S:28][C:22]3[N:21]=[C:20]([NH2:19])[CH:25]=[C:24]([NH2:26])[N+:23]=3[CH3:27])[CH2:7][S:8][C@H:9]12

Komponenten

6

Edukt 4

HCID 222AmmoniaHCID 887MethanolHCID 110081672(1H)-Pyrimidinethione, 4,6-diamino-1-methyl-HCID 113463103-Acetoxymethyl-7-amino-3cephem-4-carboxylic acid

Produkt 1

HCID 677883687-Amino-3-(4,6-diamino-1-methyl-pyrimidinium-2-yl)thiomethyl-3-cephem-4-carboxylateAusbeute 73,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Under an anhydrous condition, a solution containing 2.72 g of 3-acetoxymethyl-7-amino-3-cephem-4-carboxylic acid and 1.56 g of 4,6-diamino-1-methyl-2-(1H)pyrimidinethione suspended in 20 ml of dry acetonitrile was cooled to 0° C.; and 3.6 ml of boron trifluoride diethylether was added. The temperature of the reaction solution was increased to a room temperature, e.g., 18°-20° C.; the solution was stirred for three hours; and then 10 ml of methyl alcohol was added. The resultant solution was stirred for 10 minutes and was added with 30 ml of ice water. The pH of the solution was adjusted to 7.1 by adding aqueous ammonia solution After concentration under a reduced pressure, e.g., about 20 mmHg, the solution was adjusted to pH 3.7 with 2N-aqueous hydrochloric acid; and allowed to stand at a room temperature for 24 hrs. The precipitates resulted from the reaction solution were filtered, washed with 10 ml of distilled water and with 10 ml of methyl alcohol, and dried to give 2.69 g of the title compound as a solid.

Aufarbeitung

  1. temperatureThe temperature of the reaction solution was increased to a room temperature
  2. custome.g., 18°-20° C.
  3. concentrationAfter concentration under a reduced pressure, e.g., about 20 mmHg
  4. waitto stand at a room temperature for 24 hrs
  5. customThe precipitates resulted from the reaction solution
  6. filtrationwere filtered
  7. washwashed with 10 ml of distilled water and with 10 ml of methyl alcohol
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f878150a6292476c825b248e06fba628
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05142041

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