Trifluoroacetic acid → HCID 178433974, compound

HRID 1858520Notes

Reaction equation

HRID 1858520 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([CH2:9][C:10]([NH:12][C@@H:13]2[C:42](=[O:43])[N:15]3[C:16]([C:26]([O:28]C(C4C=CC=CC=4)C4C=CC=CC=4)=[S:27])=[C:17]([C:20]4[S:21][C:22]([CH3:25])=[N:23][N:24]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2].FC(F)(F)C(O)=O.C(OC(C)C)(C)C>ClCCl.C1(OC)C=CC=CC=1>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([CH2:9][C:10]([NH:12][C@@H:13]2[C:42](=[O:43])[N:15]3[C:16]([C:26]([OH:28])=[S:27])=[C:17]([C:20]4[S:21][C:22]([CH3:25])=[N:23][N:24]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 131722174HCID 131722174, compound

Product 1

HCID 178433974HCID 178433974, compoundYield 54.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

To a solution of benzhydryl 7β-[2-(2-formylaminothiazol-4-yl)acetamido]-3-(5-methyl-1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylate (1.2 g) in a mixture of dichloromethane (3.6 ml) and anisole (1.2 ml) was added trifluoroacetic acid (2.4 ml) under ice-cooling. The mixture was stirred at the same temperature for 45 minutes. The reaction mixture was poured into diisopropyl ether (80 ml) and the resulting precipitate was collected by filtration and dried in vacuo. The precipitate was dissolved in a mixture of aqueous sodium hydrogen carbonate (40 ml), tetrahydrofuran (20 ml) and ethyl acetate (40 ml). To the separated aqueous solution were added ethyl acetate (40 ml) and tetrahydrofuran (20 ml). The mixture was adjusted to pH 1.8 with 1N-hydrochloric acid. The organic layer was washed with saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The residue was triturated with ethyl acetate to give 7β-[2-(2-formylaminothiazol-4-yl)acetamido]-3-(5-methyl-1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylic acid (490 mg).

Workup

  1. temperaturecooling
  2. filtrationthe resulting precipitate was collected by filtration
  3. customdried in vacuo
  4. dissolutionThe precipitate was dissolved in a mixture of aqueous sodium hydrogen carbonate (40 ml), tetrahydrofuran (20 ml) and ethyl acetate (40 ml)
  5. additionTo the separated aqueous solution were added ethyl acetate (40 ml) and tetrahydrofuran (20 ml)
  6. washThe organic layer was washed with saturated aqueous sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-5a041314bed34450b0920b95401b20cc
Source dataset
uspto-grants-2000_11
Patent number
US06150351

Reaction notes

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