Water → HCID 131714627, Verbindung

HRID 1380964

Reaktionsgleichung

Reaktionsgleichung von HRID 1380964
[C:1]([O:5][C:6]([NH:8][CH:9]1[C:46](=[O:47])[N:11]2[C:12]([C:30]([O:32][CH:33]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:31])=[C:13]([CH:17]=[CH:18]OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:14][S:15](=[O:16])[C@H:10]12)=[O:7])([CH3:4])([CH3:3])[CH3:2].[SH:48][C:49]1[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=1.C(N(C(C)C)CC)(C)C.O>CN(C)C=O.C(OC(=O)C)C>[C:1]([O:5][C:6]([NH:8][CH:9]1[C:46](=[O:47])[N:11]2[C:12]([C:30]([O:32][CH:33]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[O:31])=[C:13]([CH:17]=[CH:18][S:48][C:49]3[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=3)[CH2:14][S:15](=[O:16])[C@H:10]12)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

7

Edukt 4

HCID 962WaterHCID 276913-MercaptopyridineHCID 81531DiisopropylethylamineHCID 131714628HCID 131714628, Verbindung

Produkt 1

HCID 131714627HCID 131714627, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of benzhydryl 7-tert-butoxycarbonylamino-3-(2-tosyloxyvinyl)-3-cephem-4-carboxylate-1-oxide (trans isomer) (7 g) and 3-mercaptopyridine (1.33 g) in dimethylformamide (50 ml) containing diisopropylethylamine (4.5 g) was stirred at ambient temperature for 2 hours. The resulting solution was poured into a mixture of ice-cooled water (200 ml) and ethylacetate (200 ml). The separated organic layer was washed in turn with water, 10% aqueous hydrochloric acid and a saturated aqueous solution of sodium bicarbonate and brine. The solvent was evaporated in vacuo to give benzhydryl 7-tert-butoxycarbonylamino-3-[2-(3-pyridyl)thiovinyl]-3-cephem-4-carboxylate-1-oxide. (trans isomer) (5.2 g).

Aufarbeitung

  1. additionThe resulting solution was poured into a mixture of ice-
  2. washThe separated organic layer was washed in turn with water, 10% aqueous hydrochloric acid
  3. customThe solvent was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e9e5d473d9004752875b0119cd13f1df
Quelldatensatz
uspto-grants-1986_04
Patentnummer
US04584290

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