Trifluoroacetic acid → 7-Amino-3vinyl-3-cephem-4-carboxylic acid

HRID 569373

Reaktionsgleichung

Reaktionsgleichung von HRID 569373
C(=[N:9][CH:10]1[C:35](=[O:36])[N:12]2[C:13]([C:19]([O:21]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:20])=[C:14]([CH:17]=[CH2:18])[CH2:15][S:16][C@H:11]12)C1C(=CC=CC=1)O.FC(F)(F)C(O)=O.C(OC(C)C)(C)C>C(Cl)Cl.C1(OC)C=CC=CC=1>[NH2:9][CH:10]1[C:35](=[O:36])[N:12]2[C:13]([C:19]([OH:21])=[O:20])=[C:14]([CH:17]=[CH2:18])[CH2:15][S:16][C@H:11]12

Komponenten

6

Edukt 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 136460592HCID 136460592, Verbindung

Produkt 1

HCID 128180067-Amino-3vinyl-3-cephem-4-carboxylic acidAusbeute 54,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 7519AnisoleLösungsmittel

Versuchsvorschrift

To a solution of benzhydryl 7-salicylideneamino-3-vinyl-3-cephem-4-carboxylate (1.6 g) in methylene chloride (20 ml) and anisole (5 ml) was added dropwise trifluoroacetic acid (6 ml) with stirring, and the stirring was continued at ambient temperature for an hour. The reaction mixture was poured into diisopropyl ether, and the precipitates were collected by filtration and then suspended in water, followed by adjusting to pH 3.5 with a saturated aqueous sodium bicarbonate. The solid was collected by filtration to give 7-amino-3-vinyl-3-cephem-4-carboxylic acid (0.4 g).

Aufarbeitung

  1. waitthe stirring was continued at ambient temperature for an hour
  2. filtrationthe precipitates were collected by filtration
  3. filtrationThe solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-5d38b4a9ac3848388ab573dcc173fb25
Quelldatensatz
uspto-grants-1988_03
Patentnummer
US04731443

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