Trifluoroacetic acid → HCID 178520258, compound

HRID 1858530Notes

Reaction equation

HRID 1858530 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:48](=[O:49])[N:13]3[C:14]([C:32]([O:34]C(C4C=CC=CC=4)C4C=CC=CC=4)=[S:33])=[C:15]([C:18]4[S:19][CH:20]=[C:21]([C:23]5[CH:28]=[CH:27][C:26]([C:29]([OH:31])=[O:30])=[CH:25][CH:24]=5)[N:22]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[K].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:48](=[O:49])[N:13]3[C:14]([C:32]([OH:34])=[S:33])=[C:15]([C:18]4[S:19][CH:20]=[C:21]([C:23]5[CH:28]=[CH:27][C:26]([C:29]([OH:31])=[O:30])=[CH:25][CH:24]=5)[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 131722184HCID 131722184, compound

Product 1

HCID 178520258HCID 178520258, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of potassium benzhydryl 7β-(2-phenylacetamido)-3-[4-(4-carboxyphenyl)thiazol-2-yl]thio-3-cephem-4-carboxylate (450 mg), anisole (0.45 ml) and dichloromethane (1.35 ml) was added trifluoroacetic acid (0.9 ml) at 15° C. After stirring at room temperature for 1.5 hours, the solution was poured into diisopropyl ether. The resulting precipitate was collected by filtration, added to a mixture of tetrahydrofuran (10 ml) and water (15 ml), and the solution was adjusted to pH 7.2 with an aqueous sodium hydrogen carbonate. 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 powder was collected by filtration and dried in vacuo to give 7β-(2-phenylacetamido)-3-[4-(4-carboxyphenyl)thiazol-2-yl]thio-3-cephem-4-carboxylic acid (75 mg).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. additionadded to a mixture of tetrahydrofuran (10 ml) and water (15 ml)
  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 powder was collected by filtration
  9. customdried in vacuo

Sources & evidence

ORD record
ord-8f1f5801a60f48389378280ce7a46a18
Source dataset
uspto-grants-2000_11
Patent number
US06150351

Reaction notes

Loading…