Pyridine → Benzhydryl 7-amino-3vinyl-3cephem-4-carboxylate hydrochloride

HRID 569380

Reaktionsgleichung

Reaktionsgleichung von HRID 569380
P(Cl)(Cl)(Cl)(Cl)[Cl:2].N1C=CC=CC=1.C(OC(C(NC(OCC)=O)CCCC([NH:35][CH:36]1[C:61](=[O:62])[N:38]2[C:39]([C:45]([O:47][CH:48]([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)[C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)=[O:46])=[C:40]([CH:43]=[CH2:44])[CH2:41][S:42][C@H:37]12)=O)=O)(C1C=CC=CC=1)C1C=CC=CC=1.COCCO>C(Cl)CCl.O>[ClH:2].[NH2:35][CH:36]1[C:61](=[O:62])[N:38]2[C:39]([C:45]([O:47][CH:48]([C:49]3[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=3)[C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)=[O:46])=[C:40]([CH:43]=[CH2:44])[CH2:41][S:42][C@H:37]12

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 80192-MethoxyethanolHCID 24819Phosphorus pentachlorideHCID 14099864Benzhydryl 7-(5-benzhydryloxycarbonyl-5-ethoxycarbonylaminopentanamido)-3-vinyl-3-cephem-4-carboxylate

Produkt 1

HCID 12818005Benzhydryl 7-amino-3vinyl-3cephem-4-carboxylate hydrochlorideAusbeute 36,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of phosphorus pentachloride (7.87 g) in ethylene chloride (47.75 ml) was added pyridine (2.99 g) at 5° to 6° C. After stirring for 30 minutes, to the mixture was added benzhydryl 7-(5-benzhydryloxycarbonyl-5-ethoxycarbonylaminopentanamido)-3-vinyl-3-cephem-4-carboxylate (9.75 g). After stirring for 2 hours at 5° to 6° C. and cooling to -30° to -20° C., the mixture was treated with 2-methoxyethanol (7.67 ml) for 1.5 hours and then with water (10 ml) for an hour. The precipitates were collected by filtration and washed with ethyl acetate and diisopropyl alcohol to give benzhydryl 7-amino-3-vinyl-3-cephem-4-carboxylate hydrochloride (1.99 g).

Aufarbeitung

  1. stirringAfter stirring for 2 hours at 5° to 6° C.
  2. temperaturecooling to -30° to -20° C.
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with ethyl acetate and diisopropyl alcohol

Quellen und Nachweise

ORD-Eintrag
ord-a13105f7dd6740d89d0fb47d827401ab
Quelldatensatz
uspto-grants-1988_03
Patentnummer
US04731443

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