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

HRID 1075989

Reaction equation

HRID 1075989 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 26052Sodium tungstateCatalystHCID 176Acetic AcidSolvent

Procedure

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, icewater (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 aqueouos 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). Infrared Absorption Spectrum (CHCl3). 3350, 1795, 1740, 1688 cm-1.

Workup

  1. stirringThe mixture was stirred at 7° ~ 10°C for 1 hour
  2. customAfter the reaction, icewater (50 ml)
  3. additionwas added to the reaction mixture
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. extractionback-extracted with 5% sodium bicarbonate aqueous solution
  7. washThe aqueouos layer was washed with ethyl acetate twice
  8. extractionextracted with ethyl acetate
  9. washThe extract was washed with water
  10. customdried
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-348503be9f9f41f1bff902c03b12353b
Source dataset
uspto-grants-1976_05
Patent number
US03954732

Linked notes

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