Water → Benzhydryl 7beta-tert-butoxycarbonylamino-3-[3-formamido-2-(2-formyloxyethyl)-1-pyrazolio]methyl-3-cephem-4-carboxylate iodide

HRID 2082024Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2082024
C(OC([C@@H:8]1[C:34](=[O:35])[N:10]2[C:11]([C:18]([O:20][CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])=[C:12]([CH2:16]Cl)[CH:13](N)[S:14][C@H:9]12)=O)(C)(C)C.[I-:36].[Na+].[CH:38]([NH:40][C:41]1[N:45]([CH2:46][CH2:47][O:48][CH:49]=[O:50])[N:44]=[CH:43][CH:42]=1)=[O:39].[OH2:51]>CN(C)C=O.C(OCC)(=O)C>[I-:36].[C:12]([O:51][C:34]([NH:10][C@@H:8]1[C:34](=[O:35])[N:10]2[C:11]([C:18]([O:20][CH:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[O:19])=[C:12]([CH2:16][N+:44]3[N:45]([CH2:46][CH2:47][O:48][CH:49]=[O:50])[C:41]([NH:40][CH:38]=[O:39])=[CH:42][CH:43]=3)[CH2:13][S:14][C@H:9]12)=[O:35])([CH3:16])([CH3:13])[CH3:11]

Komponenten

7

Edukt 4

HCID 962WaterHCID 5238Sodium IodideHCID 149965672-(5-Formamido-1H-pyrazol-1-yl)ethyl formateHCID 131717748Benzhydryl 7beta-tert-butoxycarbonyl-amino-3-chloromethyl-3-cephem-4-carboxylate

Produkt 1

HCID 10259694Benzhydryl 7beta-tert-butoxycarbonylamino-3-[3-formamido-2-(2-formyloxyethyl)-1-pyrazolio]methyl-3-cephem-4-carboxylate iodide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of benzhydryl 7β-tert-butoxycarbonyl-amino-3-chloromethyl-3-cephem-4-carboxylate (20 g) and sodium iodide (5.82 g) in N,N-dimethylformamide (20 ml) was added 5-formamido-1-(2-formyloxyethyl)pyrazole (21.34 g) at room temperature. After being stirred for 24 hours at the same temperature, the mixture was poured into a mixture of water and ethyl acetate. The organic layer was separated and washed with water, aqueous sodium chloride solution, and dried over magnesium sulfate. The solution was evaporated in vacuo to give benzhydryl 7β-tert-butoxycarbonylamino-3-[3-formamido-2-(2-formyloxyethyl)-1-pyrazolio]methyl-3-cephem-4-carboxylate iodide (29.6 g).

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with water, aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customThe solution was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-76cf50f6956a4814b12c62e399c37a74
Quelldatensatz
uspto-grants-1993_02
Patentnummer
US05187160

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