Hydrogen Peroxide → p-Methoxybenzyl 7beta-amino-3-azidomethyl-3-cephem-4-carboxylate-1,1-dioxide

HRID 258009

Reaktionsgleichung

Reaktionsgleichung von HRID 258009
[NH2:1][C@@H:2]1[C:25](=[O:26])[N:4]2[C:5]([C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=[O:14])=[C:6]([CH2:9][N:10]=[N+:11]=[N-:12])[CH2:7]S[C@H:3]12.OO.[S:29]([O-:32])([O-])=[O:30].[Na+].[Na+]>C(OCC)(=O)C.O.O.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[NH2:1][C@@H:2]1[C:25](=[O:26])[N:4]2[C:5]([C:13]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=3)=[O:14])=[C:6]([CH2:9][N:10]=[N+:11]=[N-:12])[CH2:7][S:29](=[O:32])(=[O:30])[C@H:3]12

Komponenten

6

Edukt 3

HCID 784Hydrogen Peroxide2×HCID 24437Sodium SulfiteHCID 131718254p-Methoxybenzyl 7beta-amino-3-azidomethyl-3-cephem-4-carboxylate

Produkt 1

HCID 131718253p-Methoxybenzyl 7beta-amino-3-azidomethyl-3-cephem-4-carboxylate-1,1-dioxide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 150191Sodium Tungstate DihydrateKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

p-Methoxybenzyl 7β-amino-3-azidomethyl-3-cephem-4-carboxylate (17.15 g, 0.046 mol) in ethyl acetate was cooled to 15° C., sodium tungstate dihydrate (1.52 g, 0.0046 mol) was added followed by hydrogen peroxide (30%, 20.73 ml) in one portion and the stirring was continued at room temperature. After two hours an additional portion of hydrogen peroxide (5.18 ml) was added and the reaction mixture was stirred at room temperature for a total period of 18 h; the mixture was cooled to 10° C. and a solution of sodium sulphite (10%, 600 ml) was added while stirring. Organic layer was separated out, washed with aq. sodium bicarbonate solution, brine and dried (Na2SO4). Evaporation of the solvent in vacuo gave a foam (12 g) which was purified over a silica column using hexane-ethyl acetate (1:3) as eluant to give the pure product as a white foam (6.8 g, 36.5%). IR (Nujol) ν max 2083 cm-1.

Aufarbeitung

  1. customwas continued at room temperature
  2. temperaturethe mixture was cooled to 10° C.
  3. stirringwhile stirring
  4. customOrganic layer was separated out
  5. washwashed with aq. sodium bicarbonate solution, brine
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4181c31959a440168d9c37b195912fba
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05264429

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