Trifluoroacetic acid → HCID 70262478, compound

HRID 1858527Notes

Reaction equation

HRID 1858527 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:43](=[O:44])[N:13]3[C:14]([C:27]([O:29]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:28])=[C:15]([S:18][CH2:19][CH2:20][C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O.C(OC(C)C)(C)C>ClCCl.C1(OC)C=CC=CC=1>[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:43](=[O:44])[N:13]3[C:14]([C:27]([OH:29])=[O:28])=[C:15]([S:18][CH2:19][CH2:20][C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 70265971HCID 70265971, compound

Product 1

HCID 70262478HCID 70262478, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

To a solution of benzhydryl 7β-(2-phenylacetamido)-3-[2-(3-pyridyl)ethylthio]-3-cephem-4-carboxylate (632 mg) in a mixture of dichloromethane (1.8 ml) and anisole (0.6 ml) was added trifluoroacetic acid (1.2 ml) under ice-cooling. The mixture was stirred at the same temperature for 1.5 hours. The reaction mixture was poured into diisopropyl ether (60 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 (188 mg/50 ml), tetrahydrofuran (20 ml) and ethyl acetate (40 ml). To the separated aqueous layer was added tetrahydrofuran (20 ml) and ethyl acetate (40 ml), adjusted to pH 3.0 with 1N-hydrochloric acid. The resulting precipitate was collected by filtration, washed with water, ethyl acetate and n-hexane, and dried to give 7β-(2-phenylacetamido)-3-[2-(3-pyridyl)ethylthio]-3-cephem-4-carboxylic acid (366 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 (188 mg/50 ml), tetrahydrofuran (20 ml) and ethyl acetate (40 ml)
  5. additionTo the separated aqueous layer was added tetrahydrofuran (20 ml) and ethyl acetate (40 ml)
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with water, ethyl acetate and n-hexane
  8. customdried

Sources & evidence

ORD record
ord-8ac3c31113774d7a8d6ed847edcc9e37
Source dataset
uspto-grants-2000_11
Patent number
US06150351

Reaction notes

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