Hydrochloric Acid → HCID 178508513, Verbindung

HRID 992712Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 992712
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:30]/[OH:31])/[C:8]([NH:10][C@@H:11]2[C:28](=[O:29])[N:13]3[C:14]([C:25]([OH:27])=[O:26])=[C:15]([S:18][CH2:19][C:20]4[CH:21]=[N:22][NH:23][CH:24]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.C(=O)([O-])[O-].[K+].[K+].[C:38](=[O:50])([O:46][CH:47](I)[CH3:48])[O:39][CH:40]1[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1.Cl>CN(C)C(=O)C.C(OCC)(=O)C.O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:30]/[OH:31])/[C:8]([NH:10][C@@H:11]2[C:28](=[O:29])[N:13]3[C:14]([C:25]([O:27][CH2:48][CH2:47][O:46][C:38]([O:39][CH:40]4[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]4)=[O:50])=[O:26])=[C:15]([S:18][CH2:19][C:20]4[CH:21]=[N:22][NH:23][CH:24]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 9826491HCID 9826491, VerbindungHCID 111092781-Iodoethyl cyclohexyl carbonate

Produkt 1

HCID 178508513HCID 178508513, VerbindungAusbeute 3,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

To a solution of 7β-[2-(2-aminothiazol-4-yl)-2-(Z)-(hydroxyimino)acetamido]-3-[(pyrazol-4-yl)methylthio]-3-cephem-4-carboxylic acid (300 mg) in N,N-dimethylacetamide (6 ml) was added potassium carbonate (81.8 mg) under ice-cooling. After stirring at room temperature for 30 minutes, cyclohexyl 1-iodoethyl carbonate (371.47 mg) was added thereto under ice-cooling. The mixture was stirred at the same temperature for 30 minutes, poured into a mixture of water and ethyl acetate and adjusted to pH 5 with 1N hydrochloric acid. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated to give (cyclohexyloxycarbonyloxy)ethyl 7β-[2-(2-aminothiazol-4-yl)-2-(Z)-(hydroxyimino)acetamido]-3-[(pyrazol-4-yl)methylthio]-3-cephem-4-carboxylate (15.8 mg).

Aufarbeitung

  1. temperaturecooling
  2. temperatureunder ice-cooling
  3. stirringThe mixture was stirred at the same temperature for 30 minutes
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-21ae93ca2a8947fe9e7a7f8a661de684
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06468995B1

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