Sulfamic Acid → HCID 70463777, Verbindung

HRID 1902912Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1902912
[CH3:1][Si:2]([CH3:12])([CH3:11])N1CCCCCC1=O.[CH3:13][C:14]1[CH2:15][S:16](=[O:36])[C@@H:17]2[CH:24]([NH:25][C:26](=[O:34])[CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:23](=[O:35])[N:18]2[C:19]=1[C:20]([OH:22])=[O:21].NS(O)(=O)=O.[Br:42]N1C(=O)CCC1=O>ClCCl>[Br:42][CH2:13][C:14]1[CH2:15][S:16](=[O:36])[C@@H:17]2[CH:24]([NH:25][C:26](=[O:34])[CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:23](=[O:35])[N:18]2[C:19]=1[C:20]([O:22][Si:2]([CH3:12])([CH3:11])[CH3:1])=[O:21]

Komponenten

6

Edukt 4

HCID 5987Sulfamic AcidHCID 67184N-bromobutanimideHCID 114239991-Trimethylsilanyl-azepan-2-oneHCID 70485748HCID 70485748, Verbindung

Produkt 1

HCID 70463777HCID 70463777, VerbindungAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

255 mg of N-trimethylsilylcaprolactam (1.36 mmoles) were added to a refluxing suspension of 360 mg (1.03 mmoles) of 3-methyl-7-phenylacetamido-3-cephem-4-carboxylic acid-1-oxide in 25 ml of dichloromethane and a clear, colorless solution was obtained within 2 minutes. Refluxing was continued for another 25 minutes and the solution was cooled in an ice-bath and diluted to 40 ml with dichloromethane 150 mg of amidosulfonic acid (1.53 mmoles) were added thereto and bromination was carried out in half an hour using 299 mg (1.68 mmoles) of N-bromosuccinimide as the brominating agent to obtain a 51% yield of trimethylsilyl 3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylate-1-oxide.

Aufarbeitung

  1. customa clear, colorless solution was obtained within 2 minutes
  2. temperatureRefluxing
  3. temperaturethe solution was cooled in an ice-bath
  4. additionwere added
  5. waitbromination was carried out in half an hour

Quellen und Nachweise

ORD-Eintrag
ord-901ed1fc421e44b78af5e6eded5543cb
Quelldatensatz
uspto-grants-1982_12
Patentnummer
US04366315

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