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Hydrogen Peroxide → 2,2,2-Trichloroethyl 6-(2-phenylacetamido)-2,2-dimethylpenam-3-carboxylate-1-oxide

HRID 436458
Notes
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Reaction equation

HRID 436458 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][CH2:22][C:23]([Cl:26])([Cl:25])[Cl:24])=[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.O.[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][CH2:22][C:23]([Cl:24])([Cl:25])[Cl:26])=[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 129174122,2,2-Trichloroethyl 6-(2-phenylacetamido)-2,2-dimethylpenam-3-carboxylate

Product 1

HCID 122939442,2,2-Trichloroethyl 6-(2-phenylacetamido)-2,2-dimethylpenam-3-carboxylate-1-oxide

Reagents, catalysts & solvents 2

HCID 150191Sodium Tungstate Dihydrate
Catalyst
HCID 176Acetic AcidSolvent

Procedure

Sodium tungstate dihydrate (500 mg.) was added to a solution of 2,2,2-trichloroethyl 6-(2-phenylacetamido)-2,2-dimethylpenam-3-carboxylate (31.5 g.) in acetic acid (150 cc.), and to the mixture was added, dropwise, 30% hydrogen peroxide (9.1 cc ) while cooling in an ice bath. The mixture was stirred for 1.5 hours, and then water was added thereto. The precipitate was collected by filtration, washed with water and dried to yield crystals (33.2 g.) of 2,2,2-trichloroethyl 6-(2-phenylacetamido)-2,2-dimethylpenam-3-carboxylate-1-oxide, m.p. 165.5° - 168.5° C.

Workup

  1. additionto the mixture was added
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-ea388b605c344e8ba5673ff85afb3b33
Source dataset
uspto-grants-1977_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04009159

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes