Trifluoroacetic acid → HCID 131714376, compound

HRID 980996Notes

Reaction equation

HRID 980996 reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH:9]1[C:40](=[O:41])[N:11]2[C:12]([C:24]([O:26]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:25])=[C:13]([CH:16]=[CH:17][C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH2:14][S:15][C@H:10]12.C1(OC)C=CC=CC=1.C(OC(C)C)(C)C>ClCCl>[NH2:8][CH:9]1[C:40](=[O:41])[N:11]2[C:12]([C:24]([OH:26])=[O:25])=[C:13]([CH:16]=[CH:17][C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH2:14][S:15][C@H:10]12

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 7914Diisopropyl EtherHCID 131714377HCID 131714377, compound

Product 1

HCID 131714376HCID 131714376, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (15.2 ml) was added to a suspension of benzhydryl 7-amino-3-[2-(3-pyridyl)vinyl]-3-cephem-4-carboxylate (cis-trans mixture) (8.0 g) and anisole (7.4 ml) in dichloromethane (40 ml) at ambient temperature and the mixture was stirred for 1.5 hours at the same temperature. To the resulting solution was added diisopropyl ether (200 ml) and stirred. The precipitate was collected by filtration and washed with diisopropyl ether. The precipitate was added to a mixture of water and ethyl acetate and the mixture was adjusted to pH 7 with 20% potassium carbonate. The separated aqueous layer was adjusted to pH 4.5 with 10% hydrochloric acid under ice-cooling. The precipitate, whose main component was the desired trans isomer, was filtered off and added to water. The mixture was adjusted to pH 7.0 with saturated aqueous sodium bicarbonate. After removal of an insoluble substance, the aqueous filtrate was adjusted to pH 4.5 with 10% hydrochloric acid under ice-cooling. The resulting precipitate was filtered, washed with ice-cooled water and dried over phosphorus pentoxide in vacuo to give 7-amino-3-[2-(3-pyridyl)vinyl]-3-cephem-4-carboxylic acid (trans isomer) (1.9 g).

Workup

  1. stirringstirred
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with diisopropyl ether
  4. additionThe precipitate was added to a mixture of water and ethyl acetate
  5. temperaturecooling
  6. filtrationwas filtered off
  7. additionadded to water
  8. customAfter removal of an insoluble substance
  9. temperaturecooling
  10. filtrationThe resulting precipitate was filtered
  11. washwashed with ice-
  12. temperaturecooled water
  13. dry with materialdried over phosphorus pentoxide in vacuo

Sources & evidence

ORD record
ord-58b5d01f82e2434398f9e8f7648968fe
Source dataset
uspto-grants-1987_01
Patent number
US04639448

Reaction notes

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