Dicyclohexylcarbodiimide → 3-Carbamoyloxymethyl-7-(2-oxo-2,3-dihydrothiazol-4-yl)acetamido-3-cephem-4-carboxylic acid

HRID 127095

Reaktionsgleichung

Reaktionsgleichung von HRID 127095
[O:1]=[C:2]1[NH:6][C:5]([CH2:7][C:8]([OH:10])=O)=[CH:4][S:3]1.ON1C(=O)CCC1=O.C1(N=C=NC2CCCCC2)CCCCC1.[C:34]([O:37][CH2:38][C:39]1[CH2:40][S:41][C@@H:42]2[CH:49]([NH2:50])[C:48](=[O:51])[N:43]2[C:44]=1[C:45]([OH:47])=[O:46])(=[O:36])[NH2:35].C[Si](CC(N)=O)(C)C>O1CCCC1.C(OCC)(=O)C.O>[C:34]([O:37][CH2:38][C:39]1[CH2:40][S:41][C@@H:42]2[CH:49]([NH:50][C:8](=[O:10])[CH2:7][C:5]3[NH:6][C:2](=[O:1])[S:3][CH:4]=3)[C:48](=[O:51])[N:43]2[C:44]=1[C:45]([OH:47])=[O:46])(=[O:36])[NH2:35]

Komponenten

9

Edukt 5

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 127847593-Carbamoyloxymethyl-7-amino-3-cephem-4-carboxylic acidHCID 131325982-Oxo-2,3-dihydrothiazol-4-ylacetic acid

Produkt 1

HCID 705724003-Carbamoyloxymethyl-7-(2-oxo-2,3-dihydrothiazol-4-yl)acetamido-3-cephem-4-carboxylic acidAusbeute 5,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 2-oxo-2,3-dihydrothiazol-4-ylacetic acid (0.4 g.) and N-hydroxysuccinimide (0.3 g.) in tetrahydrofuran (15 ml.) was added N,N'-dicyclohexylcarbodiimide (0.52 g.) with stirring at room temperature, and the mixture was further stirred for 2 hours at the same temperature. Thus obtained solution was added to a solution of 3-carbamoyloxymethyl-7-amino-3-cephem-4-carboxylic acid (0.816 g.) and trimethylsilylacetamide (0.27 g.) in ethyl acetate (30 ml.) at room temperature, and the mixture was stirred for 16 hours at the same temperature. After the reaction, the reaction mixture was cooled to at -20° C., and then water (20 ml.) was added thereto. After stirring the mixture sufficiently, the mixture was filtered, and then the ethyl acetate layer was separated therefrom. The ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, treated with activated carbon, and then the solvent was distilled off under reduced pressure. The residue was pulverized in diethyl ether, collected by filtration and then dried to give 3-carbamoyloxymethyl-7-(2-oxo-2,3-dihydrothiazol-4-yl)acetamido-3-cephem-4-carboxylic acid (60 mg.).

Aufarbeitung

  1. stirringthe mixture was further stirred for 2 hours at the same temperature
  2. stirringthe mixture was stirred for 16 hours at the same temperature
  3. customAfter the reaction
  4. temperaturethe reaction mixture was cooled to at -20° C.
  5. stirringAfter stirring the mixture sufficiently
  6. filtrationthe mixture was filtered
  7. customthe ethyl acetate layer was separated
  8. washThe ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride
  9. dry with materialdried over magnesium sulfate
  10. additiontreated with activated carbon
  11. distillationthe solvent was distilled off under reduced pressure
  12. filtrationcollected by filtration
  13. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5c293cd717ea436daa20727f75ed10fa
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04254260

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