Water → HCID 70603589, compound

HRID 236925Notes

Reaction equation

HRID 236925 reaction equation
[C:1]1(C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:8](=[O:11])(O)[O-].[Na+].Cl[N:14]1[C:18](=[O:19])[CH2:17][CH2:16][C:15]1=O.[C:21]([O:24]CC)(=[O:23])[CH3:22].[OH2:27]>>[O:27]([CH2:17][C:18]([NH:14][CH:15]1[C:18](=[O:19])[N:14]2[CH:22]([C:21]([OH:24])=[O:23])[C:16](=[CH2:15])[CH2:17][S:8](=[O:11])[C@H:16]12)=[O:19])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 5

HCID 962WaterHCID 1140TolueneHCID 8857Ethyl AcetateHCID 31398ChlorosuccinimideHCID 23665763Sodium Bisulfite

Product 1

HCID 70603589HCID 70603589, compoundYield 35%

Procedure

To 200 ml. of dried toluene were added 4.95 g. (10 mmol) of 4'-methoxybenzyl 6-phenoxyacetamido-2,2-dimethylpenam-3-carboxylate-1-oxide and 5.2 g. (50 mmol) of sodium bisulfite. The mixture was heated at reflux, and 1.5 g. (11 mmol) of N-chlorosuccinimide were added. The mixture then was stirred and refluxed for one hour after which it was cooled in an ice bath, and 1.3 gms. (11 mmol) of stannic chloride were added. The mixture then was stirred at room temperature for about 2 hours after which it was poured into a mixture of ethyl acetate and water. The organic layer was separated and washed successively with 5 percent hydrochloric acid and brine. The organic layer then was extracted with 5 percent sodium bicarbonate solution. The extract was slurried with ethyl acetate, and acidified to pH 2.5. The ethyl acetate layer was separated, washed with water, dried over magnesium sulfate, and concentrated in vacuo to a small volume from which 1.3 gms. (35 percent) of the title compound were obtained as crystals. Analysis of the product by nmr was consistent with the structure of the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux
  3. temperaturerefluxed for one hour after which it
  4. temperaturewas cooled in an ice bath
  5. stirringThe mixture then was stirred at room temperature for about 2 hours after which it
  6. customThe organic layer was separated
  7. washwashed successively with 5 percent hydrochloric acid and brine
  8. extractionThe organic layer then was extracted with 5 percent sodium bicarbonate solution
  9. customThe ethyl acetate layer was separated
  10. washwashed with water
  11. dry with materialdried over magnesium sulfate
  12. concentrationconcentrated in vacuo to a small volume from which 1.3 gms

Sources & evidence

ORD record
ord-df8607ebf8a9452fbedfdb841032fbfe
Source dataset
uspto-grants-1979_06
Patent number
US04159266

Reaction notes

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