Trifluoroacetic acid → HCID 131712194, compound

HRID 1703033Notes

Reaction equation

HRID 1703033 reaction equation
C1(OC)C=CC=CC=1.[CH3:9][O:10][N:11]=[C:12]([C:51]1[N:52]=[N:53][S:54][CH:55]=1)[C:13]([NH:15][C:16]1([O:49][CH3:50])[C:47](=[O:48])[N:18]2[C:19]([C:31]([O:33]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:32])=[C:20]([CH2:23][S:24][C:25]3[N:29]([CH3:30])[N:28]=[N:27][N:26]=3)[CH2:21][S:22][C@H:17]12)=[O:14].FC(F)(F)C(O)=O>ClCCCl>[CH3:9][O:10][N:11]=[C:12]([C:51]1[N:52]=[N:53][S:54][CH:55]=1)[C:13]([NH:15][C:16]1([O:49][CH3:50])[C:47](=[O:48])[N:18]2[C:19]([C:31]([OH:33])=[O:32])=[C:20]([CH2:23][S:24][C:25]3[N:29]([CH3:30])[N:28]=[N:27][N:26]=3)[CH2:21][S:22][C@H:17]12)=[O:14]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 131712193HCID 131712193, compound

Product 1

HCID 131712194HCID 131712194, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Anisole (0.86 ml.) was added at ambient temperature to a solution of diphenylmethyl 7-[2-methoxyimino-2-(1,2,3-thiadiazol-4-yl)acetamido]-7-methoxy-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylate (syn isomer) (0.86 g.) in dry 1,2-dichloroethane (10 ml.), and then trifluoroacetic acid (1.68 g.) was added dropwise thereto under ice-cooling. The resulting mixture was stirred for 2 hours under ice-cooling and the reaction mixture was concentrated under reduced pressure. To the residue were added ethyl acetate (20 ml.) and water (20 ml.). After shaking the mixture, the ethyl acetate layer was separated. The remaining aqueous layer was further extracted with ethyl acetate (10 ml. and 5 ml.). The ethyl acetate layers were combined and 10% aqueous solution of dipotassium hydrogen phosphate (20 ml.) was added thereto. The mixture was shaken and the aqueous layer was separated. The ethyl acetate layer was further extracted with 10% aqueous solution of dipotassium hydrogen phosphate (10 ml. and 5 ml.). The aqueous layers were combined and washed in turn with ethyl acetate (10 ml. and 5 ml.) and ether (10 ml.). The remaining solvent in the aqueous layer was removed by bubbling of nitrogen gas. The resulting aqueous layer was adjusted to pH 2 with 10% hydrochloric acid under ice-cooling. Precipitates were collected by filtration, washed with water and dried over phosphorus pentoxide under reduced pressure to give 7-[2-methoxyimino-2-(1,2,3-thiadiazol-4-yl)acetamido]-7-methoxy-3-(1-methyl-1H-tetrazol-5yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (0.21 g.).

Workup

  1. temperatureunder ice-cooling
  2. temperaturecooling
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. additionTo the residue were added ethyl acetate (20 ml.) and water (20 ml.)
  5. stirringAfter shaking the mixture
  6. customthe ethyl acetate layer was separated
  7. extractionThe remaining aqueous layer was further extracted with ethyl acetate (10 ml. and 5 ml.)
  8. addition10% aqueous solution of dipotassium hydrogen phosphate (20 ml.) was added
  9. stirringThe mixture was shaken
  10. customthe aqueous layer was separated
  11. extractionThe ethyl acetate layer was further extracted with 10% aqueous solution of dipotassium hydrogen phosphate (10 ml. and 5 ml.)
  12. washwashed in turn with ethyl acetate (10 ml. and 5 ml.) and ether (10 ml.)
  13. customThe remaining solvent in the aqueous layer was removed
  14. customby bubbling of nitrogen gas
  15. temperaturecooling
  16. customPrecipitates
  17. filtrationwere collected by filtration
  18. washwashed with water
  19. dry with materialdried over phosphorus pentoxide under reduced pressure

Sources & evidence

ORD record
ord-20f95c1bd42445eba24977e4ebc214ca
Source dataset
uspto-grants-1982_09
Patent number
US04350693

Reaction notes

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