Sulfamic Acid → HCID 70463851, Verbindung

HRID 1902921Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1902921
[CH3:1][Si:2]([CH3:8])([CH3:7])NC(=O)C.[C:9]([NH:17][CH:18]1[C:30](=[O:31])[N:20]2[C:21]([C:27]([OH:29])=[O:28])=[C:22]([CH3:26])[CH2:23][S:24](=[O:25])[C@H:19]12)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.NS(O)(=O)=O.[Br:37]N1C(=O)CCC1=O>ClCCl>[C:9]([NH:17][CH:18]1[C:30](=[O:31])[N:20]2[C:21]([C:27]([O:29][Si:2]([CH3:8])([CH3:7])[CH3:1])=[O:28])=[C:22]([CH2:26][Br:37])[CH2:23][S:24](=[O:25])[C@H:19]12)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

6

Edukt 4

HCID 5987Sulfamic AcidHCID 25989Acetamide, N-(trimethylsilyl)-HCID 67184N-bromobutanimideHCID 704647027-Benzamido-3-methyl-3-cephem-4-carboxylic acid-1-oxide

Produkt 1

HCID 70463851HCID 70463851, VerbindungAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

208 mg of N-trimethylsilylacetamide (1.59 mmoles) were added to a suspension of 383 mg (1.14 mmoles) of 7-benzamido-3-methyl-3-cephem-4-carboxylic acid-1-oxide in 25 ml of dichloromethane, and after stirring for 11/2 hours at room temperature, a clear solution was obtained, which was diluted with dichloromethane to 50 ml. 200 mg of amidosulfonic acid (1.04 mmoles) were added thereto and the mixture was cooled in an ice-bath. Bromination was carried out in half an hour using 310 mg (1.74 mmoles) of N-bromosuccinimide as the brominating agent to obtain a 48% yield of trimethylsilyl 7-benzamido-3-bromomethyl-3-cephem-4-carboxylate-1-oxide.

Aufarbeitung

  1. customa clear solution was obtained
  2. temperaturethe mixture was cooled in an ice-bath
  3. waitBromination was carried out in half an hour

Quellen und Nachweise

ORD-Eintrag
ord-e56895226ad148ef9fa9bdfb31a824ae
Quelldatensatz
uspto-grants-1982_12
Patentnummer
US04366315

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