Sulfamic Acid → HCID 70463851, Verbindung

HRID 1902920Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1902920
CN([Si:9]([CH3:12])([CH3:11])[CH3:10])C(=O)C(F)(F)F.[C:13]([NH:21][CH:22]1[C:34](=[O:35])[N:24]2[C:25]([C:31]([OH:33])=[O:32])=[C:26]([CH3:30])[CH2:27][S:28](=[O:29])[C@H:23]12)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.NS(O)(=O)=O.[Br:41]N1C(=O)CCC1=O>ClCCl>[C:13]([NH:21][CH:22]1[C:34](=[O:35])[N:24]2[C:25]([C:31]([O:33][Si:9]([CH3:12])([CH3:11])[CH3:10])=[O:32])=[C:26]([CH2:30][Br:41])[CH2:27][S:28](=[O:29])[C@H:23]12)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

6

Edukt 4

HCID 5987Sulfamic AcidHCID 32510N-methyl-N-(trimethylsilyl)trifluoroacetamideHCID 67184N-bromobutanimideHCID 704647027-Benzamido-3-methyl-3-cephem-4-carboxylic acid-1-oxide

Produkt 1

HCID 70463851HCID 70463851, VerbindungAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

324 mg (1.63 mmoles) of N-methyl-N-trimethylsilyltrifluoroacetamide were added to a suspension of 409 mg (1.22 mmoles) of 7-benzamido-3-methyl-3-cephem-4-carboxylic acid-1-oxide in 25 ml of dichloromethane and after stirring at room temperature for 10 minutes, a clear, slightly yellow solution was obtained. This was diluted to 40 ml with dicloromethane and 50 mg of amidosulfonic acid (0.51 mmole) were added. This solution was cooled in an ice-bath and was brominated in one hour with 301 mg (1.70 mmoles) of N-bromosuccinimide to obtain a yield of 59% of trimethylsilyl 7-benzamido-3-bromomethyl-3-cephem-4-carboxylate-1-oxide.

Aufarbeitung

  1. customa clear, slightly yellow solution was obtained
  2. additionwere added
  3. temperatureThis solution was cooled in an ice-bath

Quellen und Nachweise

ORD-Eintrag
ord-890771214c054e29b794457644896bf6
Quelldatensatz
uspto-grants-1982_12
Patentnummer
US04366315

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