Trifluoroacetic acid → HCID 178525231, compound

HRID 1858515Notes

Reaction equation

HRID 1858515 reaction equation
[K].[C:2]1([CH2:8][C:9]([NH:11][C@@H:12]2[C:44](=[O:45])[N:14]3[C:15]([C:28]([O:30]C(C4C=CC=CC=4)C4C=CC=CC=4)=[S:29])=[C:16]([C:19]4[S:20][CH:21]=[C:22]([CH2:24][C:25]([OH:27])=[O:26])[N:23]=4)[CH2:17][S:18][C@H:13]23)=[O:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(OC(C)C)(C)C>ClCCl>[C:2]1([CH2:8][C:9]([NH:11][C@@H:12]2[C:44](=[O:45])[N:14]3[C:15]([C:28]([OH:30])=[S:29])=[C:16]([C:19]4[S:20][CH:21]=[C:22]([CH2:24][C:25]([OH:27])=[O:26])[N:23]=4)[CH2:17][S:18][C@H:13]23)=[O:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 7914Diisopropyl EtherHCID 131722162HCID 131722162, compound

Product 1

HCID 178525231HCID 178525231, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of benzhydryl 7β-(2-phenylacetamido)-3-(4-carboxymethylthiazol-2-yl)thio-3-cephem-4-carboxylate potassium salt (1.10 g), anisole (1.10 ml) and dichloromethane (3.30 ml) was added trifluoroacetic acid (2.20 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 and water and adjusted to pH 7.2 with an aqueous sodium bicarbonate. The separated aqueous solution was 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. Ethyl acetate was added to the residue and the resulting crystal was collected by filtration to give 7β-(2-phenylacetamido)-3-(4-carboxymethylthiazol-2-yl)thio-3-cephem-4-carboxylic acid (595 mg).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. additionadded to a mixture of tetrahydrofuran and water
  3. extractionextracted with tetrahydrofuran
  4. washThe tetrahydrofuran solution was washed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. additionEthyl acetate was added to the residue
  8. filtrationthe resulting crystal was collected by filtration

Sources & evidence

ORD record
ord-2fa103931b4040aebb3e3cabc9002822
Source dataset
uspto-grants-2000_11
Patent number
US06150351

Reaction notes

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