Trifluoroacetic acid → HCID 70617609, compound

HRID 372870Notes

Reaction equation

HRID 372870 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:43](=[O:44])[N:12]2[C:13]([C:27]([O:29]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:28])=[C:14]([CH:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH3:18])[CH2:15][S:16][C@H:11]12)=[O:8].C1([O:51]C)C=CC=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:43](=[O:44])[N:12]2[C:13]([C:27]([OH:29])=[O:28])=[C:14]([CH:17]([O:19][C:20](=[O:51])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH3:18])[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 70617671HCID 70617671, compound

Product 1

HCID 70617609HCID 70617609, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of diphenylmethyl 7-(2-thienylacetamido)-3-(1-benzyloxyethyl)-3-cephem-4-carboxylate (stereoisomer A: 160 mg) in methylene chloride (1.6 ml) are added anisole (0.32 ml) and trifluoroacetic acid (0.32 ml). After 15 minutes, the reaction mixture is evaporated to dryness, and the obtained residue is dissolved in ethyl acetate. The solution is extracted with aqueous sodium hydrogen carbonate solution. The extract solution is evaporated with ethyl acetate, cooled with ice, stirred and neutralized with 1N-hydrochloric acid to pH 2.0, and is extracted with ethyl acetate. The extract solution is washed with saline, dried over sodium sulfate, and evaporated to give 7-(2-thienylacetamido)-3-(1-benzoyloxyethyl)-3-cephem-4-carboxylic acid (stereoisomer A: 60 mg). m.p. 114°-118° C. RF: same with the benzylamine salt described below.

Workup

  1. customthe reaction mixture is evaporated to dryness
  2. dissolutionthe obtained residue is dissolved in ethyl acetate
  3. extractionThe solution is extracted with aqueous sodium hydrogen carbonate solution
  4. customThe extract solution is evaporated with ethyl acetate
  5. temperaturecooled with ice
  6. extractionis extracted with ethyl acetate
  7. washThe extract solution is washed with saline
  8. dry with materialdried over sodium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-7e1515f9ab4d492f831f94eaeac92cde
Source dataset
uspto-grants-1978_05
Patent number
US04092474

Reaction notes

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