Trifluoroacetic acid → HCID 131714998, compound

HRID 1249421Notes

Reaction equation

HRID 1249421 reaction equation
C([O:5][C:6]([CH2:8][O:9][N:10]=[C:11]([C:43]1[N:44]=[C:45]([NH2:48])[S:46][CH:47]=1)[C:12]([NH:14][CH:15]1[C:41](=[O:42])[N:17]2[C:18]([C:25]([O:27]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:26])=[C:19](/[CH:22]=[CH:23]/[Cl:24])[CH2:20][S:21][C@H:16]12)=[O:13])=[O:7])(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C(OC(C)C)(C)C>[C:6]([CH2:8][O:9][N:10]=[C:11]([C:43]1[N:44]=[C:45]([NH2:48])[S:46][CH:47]=1)[C:12]([NH:14][CH:15]1[C:41](=[O:42])[N:17]2[C:18]([C:25]([OH:27])=[O:26])=[C:19](/[CH:22]=[CH:23]/[Cl:24])[CH2:20][S:21][C@H:16]12)=[O:13])([OH:7])=[O:5]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 131714996HCID 131714996, compound

Product 1

HCID 131714998HCID 131714998, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

To a mixture of benzhydryl 7-[2-t-butoxycarbonylmethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[(E)-2-chlorovinyl]-3-cephem-4-carboxylate (syn isomer) (2.2 g) and anisole (2.2 ml) was added trifluoroacetic acid (9.0 ml) in an ice-bath. The mixture was stirred for two hours at room temperature and poured into diisopropyl ether (180 ml). The resulting precipitates were collected by filtration and washed with diisopropyl ether. The precipitates were dissolved in an aqueous solution of sodium bicarbonate and washed with ethyl acetate. The aqueous layer was concentrated to remove organic solvent under reduced pressure, cooled to 5° C. and adjusted to pH 2.2 with diluted hydrochloric acid. The resulting precipitates were collected by filtration, washed with water and dried in vacuo to give 7-[2-carboxymethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[(E)-2-chlorovinyl]-3-cephem-4-carboxylic acid (syn isomer) (1.07 g).

Workup

  1. customThe resulting precipitates
  2. filtrationwere collected by filtration
  3. washwashed with diisopropyl ether
  4. dissolutionThe precipitates were dissolved in an aqueous solution of sodium bicarbonate
  5. washwashed with ethyl acetate
  6. concentrationThe aqueous layer was concentrated
  7. customto remove organic solvent under reduced pressure
  8. temperaturecooled to 5° C.
  9. customThe resulting precipitates
  10. filtrationwere collected by filtration
  11. washwashed with water
  12. customdried in vacuo

Sources & evidence

ORD record
ord-d8d6f882ddee494288b3c5eb6bcc8b16
Source dataset
uspto-grants-1986_12
Patent number
US04631274

Reaction notes

Loading…