Hydrogen Peroxide → 2-Bromomethyl-2-methyl-6-(2-phenoxyacetamido)penam-3-carboxylic acid-1-oxide

HRID 261257

Reaktionsgleichung

Reaktionsgleichung von HRID 261257
[Br:1][CH2:2][C:3]1([CH3:25])[CH:7]([C:8]([OH:10])=[O:9])[N:6]2[C:11](=[O:24])[CH:12]([NH:13][C:14](=[O:23])[CH2:15][O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C@H:5]2[S:4]1.[OH:26]O>C(O)(=O)C.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[Br:1][CH2:2][C:3]1([CH3:25])[CH:7]([C:8]([OH:10])=[O:9])[N:6]2[C:11](=[O:24])[CH:12]([NH:13][C:14](=[O:23])[CH2:15][O:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C@H:5]2[S:4]1=[O:26]

Komponenten

5

Edukt 2

HCID 784Hydrogen PeroxideHCID 128952582-Bromomethyl-2-methyl-6-(2-phenoxyacetamido)penam-3-carboxylic acid

Produkt 1

HCID 705901962-Bromomethyl-2-methyl-6-(2-phenoxyacetamido)penam-3-carboxylic acid-1-oxide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 26052Sodium tungstateKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Sodium tungstate (0.02 g) was added to a solution of 2-bromomethyl-2-methyl-6-(2-phenoxyacetamido)penam-3-carboxylic acid (3.1 g) in acetic acid (8 ml) at 7°-10° C. under stirring and then to the mixture was added 30% aqueous hydrogen peroxide (1.2 ml). The mixture was stirred at 7°-10° C. for 1 hour. After the reaction, ice-water (50 ml) was added to the reaction mixture and then extracted with ethyl acetate. The extract was washed with water and back-extracted with 5% sodium bicarbonate aqueous solution. The aqueous layer was washed with ethyl acetate twice, acidified with 5% hydrochloric acid to pH2 and then extracted with ethyl acetate. The extract was washed with water, dried and concentrated to give powder of 2-bromomethyl-2-methyl-6-(2-phenoxyacetamido)penam-3-carboxylic acid-1-oxide (2 g).

Aufarbeitung

  1. stirringThe mixture was stirred at 7°-10° C. for 1 hour
  2. additionwas added to the reaction mixture
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. extractionback-extracted with 5% sodium bicarbonate aqueous solution
  6. washThe aqueous layer was washed with ethyl acetate twice
  7. extractionextracted with ethyl acetate
  8. washThe extract was washed with water
  9. customdried
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-024951aec86f42c4acc7f8994a0af37a
Quelldatensatz
uspto-grants-1979_08
Patentnummer
US04164497

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