Water → Benzhydryl 7-(4-bromo-3,3-diethoxy-2-methoxyiminobutyramido)-3-vinyl-3-cephem-4-carboxylate

HRID 569343

Reaktionsgleichung

Reaktionsgleichung von HRID 569343
Cl.[NH2:2][CH:3]1[C:28](=[O:29])[N:5]2[C:6]([C:12]([O:14][CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])=[C:7]([CH:10]=[CH2:11])[CH2:8][S:9][C@H:4]12.[Br:30][CH2:31][C:32]([O:43][CH2:44][CH3:45])([O:40][CH2:41][CH3:42])[C:33](=[N:37][O:38][CH3:39])[C:34](Cl)=[O:35].O>C(OCC)(=O)C>[Br:30][CH2:31][C:32]([O:43][CH2:44][CH3:45])([O:40][CH2:41][CH3:42])[C:33](=[N:37][O:38][CH3:39])[C:34]([NH:2][CH:3]1[C:28](=[O:29])[N:5]2[C:6]([C:12]([O:14][CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:13])=[C:7]([CH:10]=[CH2:11])[CH2:8][S:9][C@H:4]12)=[O:35]

Komponenten

5

Edukt 3

HCID 962WaterHCID 12818005Benzhydryl 7-amino-3vinyl-3cephem-4-carboxylate hydrochlorideHCID 542161602-Methoxyimino-3,3-diethoxy-4-bromobutyryl chloride

Produkt 1

HCID 131713161Benzhydryl 7-(4-bromo-3,3-diethoxy-2-methoxyiminobutyramido)-3-vinyl-3-cephem-4-carboxylateAusbeute 100,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a solution of benzhydryl 7-amino-3-vinyl-3-cephem-4-carboxylate hydrochloride (6.4 g) and timethylsilylacetamide (9.8 g) in ethyl acetate (80 ml) was added 4-bromo-3,3-diethoxy-2-methoxyiminobutyryl chloride (syn isomer) (5.0 g) at -20° C. with stirring, and the stirring was continued at -20° to 5° C. for an hour. To the reaction mixture were added ethyl acetate and water, and the separated ethyl acetate solution was washed with a saturated aqueous sodium bicarbonate and an aqueous sodium chloride, followed by drying over anhydrous magnesium sulfate. Removal of the solvent gave benzhydryl 7-(4-bromo-3,3-diethoxy-2-methoxyiminobutyramido)-3-vinyl-3-cephem-4-carboxylate (syn isomer) (10.1 g).

Aufarbeitung

  1. waitthe stirring was continued at -20° to 5° C. for an hour
  2. washthe separated ethyl acetate solution was washed with a saturated aqueous sodium bicarbonate
  3. dry with materialby drying over anhydrous magnesium sulfate
  4. customRemoval of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-52c2aabe7f364e20ad7f693b6b936da7
Quelldatensatz
uspto-grants-1988_03
Patentnummer
US04731443

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