Hydrogen Peroxide → HCID 12895213, compound

HRID 2106922Notes

Reaction equation

HRID 2106922 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:27](=[O:28])[N:13]3[CH:14]([C:19]([O:21][CH:22]([CH:24]4[CH2:26][CH2:25]4)[CH3:23])=[O:20])[C:15]([CH3:18])([CH3:17])[S:16][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:29]O.O>C(O)(=O)C.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:27](=[O:28])[N:13]3[CH:14]([C:19]([O:21][CH:22]([CH:24]4[CH2:25][CH2:26]4)[CH3:23])=[O:20])[C:15]([CH3:18])([CH3:17])[S:16](=[O:29])[C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 70360869HCID 70360869, compound

Product 1

HCID 12895213HCID 12895213, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 26052Sodium tungstateCatalystHCID 176Acetic AcidSolvent

Procedure

1-cyclopropylethyl 6-(2-phenylacetamido)-2,2-dimethylpenam-3-carboxylate (1.55 g.) was dissolved in acetic acid (8 cc) and sodium tungstate (10 mg.) was added thereto. To the stirred mixture was added, dropwise, 30% hydrogen peroxide (0.53 g.) while cooling in an ice bath and the mixture was stirred for a period of 30 minutes at this temperature. Water was added to the mixture and the aqueous solution was extracted with ethyl acetate. The ethyl acetate layer was washed in turn with a saturated aqueous solution of sodium bicarbonate, water, and a saturated aqueous solution of sodium chloride, dried and concentrated. The residue was dissolved in ether and the ether solution was allowed to stand. The precipitate was collected by filtration to yield crystals (1.53 g.) of 1-cyclopropylethyl 6-(2-phenylacetamido)-2,2-dimethylpenam-3-carboxylate-1-oxide, m.p. 158°-159° C.

Workup

  1. additionTo the stirred mixture was added
  2. extractionthe aqueous solution was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed in turn with a saturated aqueous solution of sodium bicarbonate, water
  4. dry with materiala saturated aqueous solution of sodium chloride, dried
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in ether
  7. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-aee124d2e52a42a2835edce07af28e05
Source dataset
uspto-grants-1990_06
Patent number
US04931555

Reaction notes

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