p-Toluenesulfonic acid → Benzhydryl 7-salicylideneamino-3-hydroxymethyl-3-cephem-4-carboxylate

HRID 1088102Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1088102
C1(N[CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)CCCCC1.[CH:14](=[N:22][CH:23]1[C:35](=[O:36])[N:25]2[C:26]([C:32]([OH:34])=[O:33])=[C:27]([CH2:30][OH:31])[CH2:28][S:29][C@H:24]12)[C:15]1[C:16](=[CH:18][CH:19]=[CH:20][CH:21]=1)[OH:17].[C:37]1([CH3:47])[CH:42]=[CH:41][C:40](S(O)(=O)=O)=[CH:39][CH:38]=1>C(OCC)(=O)C>[CH:14](=[N:22][CH:23]1[C:35](=[O:36])[N:25]2[C:26]([C:32]([O:34][CH:47]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[O:33])=[C:27]([CH2:30][OH:31])[CH2:28][S:29][C@H:24]12)[C:15]1[C:16](=[CH:18][CH:19]=[CH:20][CH:21]=1)[OH:17]

Komponenten

4

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 136460587HCID 136460587, Verbindung

Produkt 1

HCID 136460596Benzhydryl 7-salicylideneamino-3-hydroxymethyl-3-cephem-4-carboxylateAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a suspension of 7-salicylideneamino-3-hydroxymethyl-3-cephem-4-carboxylic acid dicyclohexylamine salt (3 g) in ethyl acetate (60 ml) was added dropwise an ethyl acetate solution of p-toluenesulfonic acid (1.1 g) with stirring, and the reaction mixture was stirred for an hour at ambient temperature. After the precipitate was filtered off, the filtrate was treated with a solution of excess diphenyldiazomethane in ethyl acetate for an hour. The solvent was distilled off, and the residue was pulverized with diisopropyl ether, collected by filtration and dried to give benzhydryl 7-salicylideneamino-3-hydroxymethyl-3-cephem-4-carboxylate (2.66 g).

Aufarbeitung

  1. stirringthe reaction mixture was stirred for an hour at ambient temperature
  2. filtrationAfter the precipitate was filtered off
  3. additionthe filtrate was treated with a solution of excess diphenyldiazomethane in ethyl acetate for an hour
  4. distillationThe solvent was distilled off
  5. filtrationcollected by filtration
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-646032ee2ec8482ca183f1763bafe617
Quelldatensatz
uspto-grants-1990_10
Patentnummer
US04960889

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