Trifluoroacetic acid → HCID 178514147, compound

HRID 1858518Notes

Reaction equation

HRID 1858518 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)=[S:28])=[C:15]([C:18]4[S:19][CH:20]=[C:21]([CH2:23][C:24](=[S:26])[NH2:25])[N:22]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(OC(C)C)(C)C>ClCCl>[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])=[S:28])=[C:15]([C:18]4[S:19][CH:20]=[C:21]([CH2:23][C:24](=[S:26])[NH2:25])[N:22]=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 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 7914Diisopropyl EtherHCID 131722170HCID 131722170, compound

Product 1

HCID 178514147HCID 178514147, compoundYield 5.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of benzhydryl 7β-(2-phenylacetamido)-3-(4-thiocarbamoylmethylthiazol-2-yl)thio-3-cephem-4-carboxylate (1.46 g), anisole (1.46 ml) and dichloromethane (4.38 ml) was added trifluoroacetic acid (2.92 ml) at 15° C. After stirring at room temperature for 1 hour, the solution was poured into diisopropyl ether. The resulting precipitate was collected by filtration, added to a mixture of tetrahydrofuran, ethyl acetate and water, and adjusted to pH 7.5 with an aqueous sodium hydrogen carbonate. The separated aqueous solution was washed with ethyl acetate, adjusted to pH 3.0 with 1N-hydrochloric acid and extracted with tetrahydrofuran. The tetrahydrofuran solution was washed with saturated sodium chloride solution, dried over magnesium sulfate and evaporated under reduced pressure. The residue was subjected to preparative HPLC (eluent: pH 3 buffer/acetonitrile) to give 7β-(2-phenylacetamido)-3-(4-thiocarbamoylmethylthiazol-2-yl)thio-3-cephem-4-carboxylic acid (62 mg).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. additionadded to a mixture of tetrahydrofuran, ethyl acetate and water
  3. washThe separated aqueous solution was washed with ethyl acetate
  4. extractionextracted with tetrahydrofuran
  5. washThe tetrahydrofuran solution was washed with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-075b96eed25f493faa051f538b7f99ba
Source dataset
uspto-grants-2000_11
Patent number
US06150351

Reaction notes

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