Reacción #346354

ord-13912584cd0d47cd8a0335c54d569d09

Ecuación de reacción

CC1(C)S[C@@H]2C(NC(=O)Cc3ccccc3)C(=O)N2C1C(=O)OCC(Cl)(Cl)Cl
2,2,2-trichloroethyl 6-(2-phenylacetamido)-2,2-dimethylpenam-3-carboxylate
CC(=O)O
acetic acid
O=C([O-])[O-].O=C([O-])[O-].OO.OO.OO.[Na+].[Na+].[Na+].[Na+]
sodium percarbonate
CC(=O)O
acetic acid
→
CC1(C)C(C(=O)OCC(Cl)(Cl)Cl)N2C(=O)C(NC(=O)Cc3ccccc3)[C@H]2S1=O
2,2,2-trichloroethyl 6-(2-phenylacetamido)-2,2-dimethylpenam-3-carboxylate-1-oxide

Reactantes

CC1(C)S[C@@H]2C(NC(=O)Cc3ccccc3)C(=O)N2C1C(=O)OCC(Cl)(Cl)Cl
2,2,2-trichloroethyl 6-(2-phenylacetamido)-2,2-dimethylpenam-3-carboxylate
CC(=O)O
acetic acid
O=C([O-])[O-].O=C([O-])[O-].OO.OO.OO.[Na+].[Na+].[Na+].[Na+]
sodium percarbonate
CC(=O)O
acetic acid

Reactivos

O.O.[Na+].[Na+].[O]=[W](=[O])([O-])[O-]
sodium tungstate dihydrate

Disolventes

O
water
O
water

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.ADDITIONwas added
  2. 2
    Temperaturawhile cooling in an ice bath
  3. 3
    workup.STIRRINGThe mixture was stirred for 3 hours
  4. 4
    FiltraciónThe precipitate was collected by filtration
  5. 5
    Lavadowashed with water
  6. 6
    Otrodried

Procedimiento

2,2,2-trichloroethyl 6-(2-phenylacetamido)-2,2-dimethylpenam-3-carboxylate (466 mg.) was added to acetic acid (2 cc), and sodium percarbonate (377 mg.) was added thereto while cooling in an ice bath. The mixture was stirred for 30 minutes, and sodium tungstate dihydrate (40 mg.), acetic acid (1 cc) and water (1 cc) were added thereto. The mixture was stirred for 3 hours, and then water (50 cc) was added thereto. The precipitate was collected by filtration, washed with water and dried to yield crude crystals (400 mg.) of 2,2,2-trichloroethyl 6-(2-phenylacetamido)-2,2-dimethylpenam-3-carboxylate-1-oxide, m.p. 165° - 167° C.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04036847uspto-grants-1977_07