Sulfamic Acid → HCID 70463777, Verbindung

HRID 1902911Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1902911
[CH3:1][C:2]1[CH2:3][S:4](=[O:24])[C@@H:5]2[CH:12]([NH:13][C:14](=[O:22])[CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:11](=[O:23])[N:6]2[C:7]=1[C:8]([OH:10])=[O:9].[CH3:25][Si:26]([CH3:32])([CH3:31])NC(=O)C.NS(O)(=O)=O.[Br:38]N1C(=O)CCC1=O>ClCCl>[Br:38][CH2:1][C:2]1[CH2:3][S:4](=[O:24])[C@@H:5]2[CH:12]([NH:13][C:14](=[O:22])[CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:11](=[O:23])[N:6]2[C:7]=1[C:8]([O:10][Si:26]([CH3:32])([CH3:31])[CH3:25])=[O:9]

Komponenten

6

Edukt 4

HCID 5987Sulfamic AcidHCID 25989Acetamide, N-(trimethylsilyl)-HCID 67184N-bromobutanimideHCID 70485748HCID 70485748, Verbindung

Produkt 1

HCID 70463777HCID 70463777, VerbindungAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a refluxing suspension of 329 mg (0.95 mmole) of 3-methyl-7-phenylacetamido-3-cephem-4-carboxylic acid-1-oxide in 25 ml of dichloromethane, 298 mg (2.27 mmoles) of N-trimethylsilylacetamide were added and a clear, colorless solution was obtained after 15 minutes. Refluxing was continued for another 30 minutes after which 300 mg (3.06 mmoles) of amidosulfonic acid were added. The mixture was diluted with dichloromethane to 40 ml and cooled in an ice-bath. Bromination was carried out in one hour using 280 mg (1.57 mmoles) of N-bromosuccinimide as the brominating agent to obtain a yield of 50% of trimethylsilyl 3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylate-1-oxide.

Aufarbeitung

  1. additionwere added
  2. customa clear, colorless solution was obtained after 15 minutes
  3. temperatureRefluxing
  4. temperaturecooled in an ice-bath
  5. waitBromination was carried out in one hour

Quellen und Nachweise

ORD-Eintrag
ord-8f47359f58374c548a9c2855285f9a62
Quelldatensatz
uspto-grants-1982_12
Patentnummer
US04366315

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