Sulfamic Acid → HCID 70463851, Verbindung

HRID 1902922Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1902922
[C:1]([NH:9][CH:10]1[C:22](=[O:23])[N:12]2[C:13]([C:19]([OH:21])=[O:20])=[C:14]([CH3:18])[CH2:15][S:16](=[O:17])[C@H:11]12)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][Si:25]([CH3:33])([CH3:32])NC(OCC)=O.C[Si](OS(O[Si](C)(C)C)(=O)=O)(C)C.NS(O)(=O)=O.[Br:52]N1C(=O)CCC1=O>ClCCl>[C:1]([NH:9][CH:10]1[C:22](=[O:23])[N:12]2[C:13]([C:19]([O:21][Si:25]([CH3:33])([CH3:32])[CH3:24])=[O:20])=[C:14]([CH2:18][Br:52])[CH2:15][S:16](=[O:17])[C@H:11]12)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 5

HCID 5987Sulfamic AcidHCID 67184N-bromobutanimideHCID 87573Silanol, trimethyl-, 1,1'-sulfateHCID 11355656HCID 11355656, VerbindungHCID 704647027-Benzamido-3-methyl-3-cephem-4-carboxylic acid-1-oxide

Produkt 1

HCID 70463851HCID 70463851, VerbindungAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture consisting of 400.5 mg (1.20 mmoles) of 7-benzamido-3-methyl-3-cephem-4-carboxylic acid-1-oxide, 0.69 g (4.3 mmoles) of N-trimethylsilylurethane and 20 mg of bis-(trimethylsilyl)-sulfate in 40 ml of dichloromethane was refluxed for 3/4 hours after which a clear solution was obtained. This was cooled in an ice-bath and bromination was carried out after the addition of 200 mg (2.04 mmoles) of amidosulfonic acid using 325.3 mg (1.83 mmoles) of N-bromosuccinimide as the brominating agent. The bromination took half an hour to obtain a 65% yield of trimethylsilyl 7-benzamido-3-bromomethyl-3-cephem-4-carboxylate-1-oxide.

Aufarbeitung

  1. temperaturewas refluxed for 3/4 hours after which a clear solution
  2. customwas obtained
  3. temperatureThis was cooled in an ice-bath
  4. waitThe bromination took half an hour

Quellen und Nachweise

ORD-Eintrag
ord-1ac59a5f84754228b1d395d356081362
Quelldatensatz
uspto-grants-1982_12
Patentnummer
US04366315

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