Hydrogen Peroxide → HCID 12895213, compound

HRID 647770Notes

Reaction equation

HRID 647770 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 aquous 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 colected 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 aquous 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 colected by filtration

Sources & evidence

ORD record
ord-9a2357d2aff54f9ba730bed241245d24
Source dataset
uspto-grants-1983_10
Patent number
US04410458

Reaction notes

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