Trifluoroacetic acid → HCID 70590729, compound

HRID 1438798Notes

Reaction equation

HRID 1438798 reaction equation
[NH:1]([C:8]1([CH3:36])[CH:13]([C:14]([O:16]C(C2CC2)C)=[O:15])[N:12]2[C:22](=[O:35])[CH:23]([NH:24][C:25](=[O:34])[CH2:26][O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:11]2[S:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>>[NH:1]([C:8]1([CH3:36])[CH:13]([C:14]([OH:16])=[O:15])[N:12]2[C:22](=[O:35])[CH:23]([NH:24][C:25](=[O:34])[CH2:26][O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:11]2[S:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70590252HCID 70590252, compound

Product 1

HCID 70590729HCID 70590729, compoundYield 50.4%

Procedure

1-Cyclopropylethyl 3-anilino-3-methyl-7-(2-phenoxyacetamido)-cepham-4-carboxylate (142mg) was dissolved in ice-cooled trifluoroacetic acid (1.5 ml) and the mixture was stirred for 1 hour under ice-cooling. After the reaction, the reaction mixture was concentrated under reduced pressure. The residue was dissolved by adding ethyl acetate and extracted with 5% sodium bicarbonate aqueous solution. The extract was adjusted to pH2 with 5% hydrochloric acid and back-extracted with ethyl acetate. The extract was washed with water, dried and the solvent was distilled off. The residue (amorphous) was dissolved in methanol and to this solution was added water little by little. Precifitates were collected by filtration and dried to give powder of 3-anilino-3-methyl-7-(2-phenoxy-acetamido)cepham-4-carboxylic acid (62 mg), mp 119 to 123° C (dec.).

Workup

  1. temperaturecooling
  2. customAfter the reaction
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved
  5. additionby adding ethyl acetate
  6. extractionextracted with 5% sodium bicarbonate aqueous solution
  7. extractionback-extracted with ethyl acetate
  8. washThe extract was washed with water
  9. customdried
  10. distillationthe solvent was distilled off
  11. dissolutionThe residue (amorphous) was dissolved in methanol and to this solution
  12. additionwas added water little by little
  13. filtrationPrecifitates were collected by filtration
  14. customdried

Sources & evidence

ORD record
ord-4b5ec24741e94758a6db25071d57d72d
Source dataset
uspto-grants-1977_11
Patent number
US04056521

Reaction notes

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