Trifluoroacetic acid → HCID 88729722, compound

HRID 1656204Notes

Reaction equation

HRID 1656204 reaction equation
C(OC([N:8]([CH:19]1[C:44](=[O:45])[N:21]2[C:22]([C:28]([O:30]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:29])=[C:23]([CH:26]=[CH2:27])[CH2:24][S:25][C@H:20]12)[C:9](=[O:18])[CH:10]([C:12]1[N:13]=[C:14]([NH2:17])[S:15][CH:16]=1)[NH2:11])=O)(C)(C)C.FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>C(Cl)Cl>[NH2:17][C:14]1[S:15][CH:16]=[C:12]([CH:10]([C:9]([NH:8][CH:19]2[C:44](=[O:45])[N:21]3[C:22]([C:28]([OH:30])=[O:29])=[C:23]([CH:26]=[CH2:27])[CH2:24][S:25][C@H:20]23)=[O:18])[NH2:11])[N:13]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 131713174HCID 131713174, compound

Product 1

HCID 88729722HCID 88729722, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of benzhydryl 7-[N-tert-butoxycarbonyl-2-(2-aminothiazol-4-yl)glycinamido]-3-vinyl-3-cephem-4-carboxylate (3.9 g) in methylene chloride (20 ml) were added trifluoroacetic acid (13.7 g) and anisole (3.8 g) under ice-cooling, and the mixture was stirred at ambient temperature for an hour. After evaporation of the reaction mixture, to the residue were added water (100 ml) and ethyl acetate, followed by adjusting to pH 7 with 2N aqueous solution of sodium bicarbonate. The precipitated solid was removed by filtration and the aqueous layer was separated out. Thereto was added ethyl acetate, followed by adjusting to pH 5 with 10% hydrochloric acid. After separating out the aqueous layer, the organic solvent was completely removed therefrom by evaporation, and then the resultant aqueous solution was adjusted to pH 4 with 10% hydrochloric acid under cooling, followed by subjecting to column chromatography on a nonionic adsorption resin "Diaion HP-20" (120 ml). After washing with water (270 ml), elution was carried out with 10% isopropyl alcohol and then 30% isopropyl alcohol, and the fractions containing the desired compound were collected and evaporated under reduced pressure to give a residue, which was lyophilized to obtain 7-[2-(2-aminothiazol-4-yl)glycinamido]-3-vinyl-3-cephem-4-carboxylic acid (0.8 g).

Workup

  1. temperaturecooling
  2. customAfter evaporation of the reaction mixture
  3. additionto the residue were added water (100 ml) and ethyl acetate
  4. customThe precipitated solid was removed by filtration
  5. customthe aqueous layer was separated out
  6. additionThereto was added ethyl acetate
  7. customAfter separating out the aqueous layer
  8. customthe organic solvent was completely removed
  9. customby evaporation
  10. temperatureunder cooling
  11. washAfter washing with water (270 ml), elution
  12. addition30% isopropyl alcohol, and the fractions containing the desired compound
  13. customwere collected
  14. customevaporated under reduced pressure
  15. customto give a residue, which

Sources & evidence

ORD record
ord-3d73a00d2b0f4a12ad9f5bf3e4b115f1
Source dataset
uspto-grants-1993_10
Patent number
US05252731

Reaction notes

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