Trifluoroacetic acid → HCID 131714360, compound

HRID 464212Notes

Reaction equation

HRID 464212 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:41]1[N:42]=[C:43]([NH2:46])[S:44][CH:45]=1)[C:5]([NH:7][CH:8]1[C:39](=[O:40])[N:10]2[C:11]([C:23]([O:25]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:24])=[C:12]([CH:15]=[CH:16][C:17]3[N:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH2:13][S:14][C@H:9]12)=[O:6].FC(F)(F)C(O)=O.C(OC(C)C)(C)C>C(Cl)Cl.C1(OC)C=CC=CC=1>[CH3:1][O:2][N:3]=[C:4]([C:41]1[N:42]=[C:43]([NH2:46])[S:44][CH:45]=1)[C:5]([NH:7][CH:8]1[C:39](=[O:40])[N:10]2[C:11]([C:23]([OH:25])=[O:24])=[C:12]([CH:15]=[CH:16][C:17]3[N:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 131714359HCID 131714359, compound

Product 1

HCID 131714360HCID 131714360, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

To a solution of benzhydryl 7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[2-(3-pyridazinyl)vinyl]-3-cephem-4-carboxylate (syn isomer) (trans isomer) (0.65 g) in methylene chloride (6.5 ml) and anisole (1.5 ml) was added trifluoroacetic acid (3.0 ml) under ice-cooling with stirring. The reaction mixture was stirred at ambient temperature for 30 minutes. The resultant solution was added dropwise to diisopropyl ether (100 ml), and the precipitate was collected by filtration, dissolved in an aqueous solution of sodium bicarbonate. The aqueous layer (100 ml) was washed with ethyl acetate (50 ml) twice, concentrated to 30 ml under reduced pressure and adjusted to pH 3.0 with 10% hydrochloric acid. The precipitate was collected by filtration, washed with water and dried over phosphorus pentoxide under reduced pressure to give 7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[2-(3-pyridazinyl)vinyl]-3-cephem-4-carboxylic acid (syn isomer) (trans isomer) (0.37 g).

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred at ambient temperature for 30 minutes
  3. filtrationthe precipitate was collected by filtration
  4. dissolutiondissolved in an aqueous solution of sodium bicarbonate
  5. washThe aqueous layer (100 ml) was washed with ethyl acetate (50 ml) twice
  6. concentrationconcentrated to 30 ml under reduced pressure
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with water
  9. dry with materialdried over phosphorus pentoxide under reduced pressure

Sources & evidence

ORD record
ord-6b0ab0e0af334109a60b4a4a659fbdd4
Source dataset
uspto-grants-1985_10
Patent number
US04546101

Reaction notes

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