N-bromobutanimide → HCID 70463777, Verbindung

HRID 1902908Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1902908
[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].CN([Si:30]([CH3:33])([CH3:32])[CH3:31])C(=O)C.[Br:34]N1C(=O)CCC1=O>ClCCl>[Br:34][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:30]([CH3:33])([CH3:32])[CH3:31])=[O:9]

Komponenten

5

Edukt 3

HCID 67184N-bromobutanimideHCID 81953N-Trimethylsilyl-N-methylacetamideHCID 70485748HCID 70485748, Verbindung

Produkt 1

HCID 70463777HCID 70463777, VerbindungAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

366 mg (1.05 mmoles) of 3-methyl-7-phenylacetamido-3-cephem-4-carboxylic acid-1-oxide were silylated in one hour at room temperature by stirring in 25 ml of dichloromethane with 208 mg (1.43 mmoles) of N-methyl-N-trimethylsilylacetamide. The clear solution obtained was cooled in an ice-bath and bromination was carried out in half an hour using 282 mg (1.58 mmoles) of N-bromosuccinimide as the brominating agent to obtain a 44% yield of trimethylsilyl 3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylate-1-oxide.

Aufarbeitung

  1. customThe clear solution obtained
  2. temperaturewas cooled in an ice-bath
  3. waitbromination was carried out in half an hour

Quellen und Nachweise

ORD-Eintrag
ord-90927bbc45264603b9c31e64bfb08451
Quelldatensatz
uspto-grants-1982_12
Patentnummer
US04366315

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