Trifluoroacetic acid → HCID 131718942, compound

HRID 1734258Notes

Reaction equation

HRID 1734258 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:36][O:37][CH2:38][C:39]([O:41]C(C)(C)C)=[O:40])[C:8]([NH:10][C@@H:11]2[C:34](=[O:35])[N:13]3[C:14]([C:31]([O-:33])=[O:32])=[C:15]([CH2:18][N+:19]([CH3:30])([CH3:29])[CH2:20][C:21]4[NH:22][CH:23]=[C:24]([OH:28])[C:25](=[O:27])[CH:26]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.FC(F)(F)C(O)=O.C(OC(C)C)(C)C>C1(OC)C=CC=CC=1>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:36][O:37][CH2:38][C:39]([OH:41])=[O:40])[C:8]([NH:10][C@@H:11]2[C:34](=[O:35])[N:13]3[C:14]([C:31]([O-:33])=[O:32])=[C:15]([CH2:18][N+:19]([CH3:29])([CH3:30])[CH2:20][C:21]4[NH:22][CH:23]=[C:24]([OH:28])[C:25](=[O:27])[CH:26]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 131718938HCID 131718938, compound

Product 1

HCID 131718942HCID 131718942, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

To a suspension of 7β-[2-(2-aminothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-[N,N-dimethyl-N-{(5-hydroxy-4-oxo-1,4-dihydropyridin-2-yl)methyl}ammonio]methyl-3-cephem-4-carboxylate (syn isomer) (0.54 g) in anisole (2 ml) was dropwise added trifluoroacetic acid (8 ml) under ice-cooling with stirring. After being stirred at ambient temperature, the mixture was poured into diisopropyl ether (100 ml). The resulting precipitate was collected by filtration, washed with diisopropyl ether and dried under reduced pressure. The precipitate was dissolved in water (30 ml) at pH 7.0 and acidified to pH 1.0 with 6N hydrochloric acid. After removal of precipitated materials, the aqueous solution was subjected to column chromatography on Diaion HP-20 (50 ml). The column was washed with water and the elution was carried out with 30% aqueous methanol. The active fractions were collected and lyophilized to give 7β-[2-(2-aminothiazol-4-yl)-2-carboxymethoxyiminoacetamido]-3-[N,N-dimethyl-N-{(5-hydroxy-4-oxo-1,4-dihydropyridin-2-yl)methyl}ammonio]methyl-3-cephem-4-carboxylate (syn isomer) (0.28 g).

Workup

  1. temperaturecooling
  2. stirringAfter being stirred at ambient temperature
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with diisopropyl ether
  5. customdried under reduced pressure
  6. dissolutionThe precipitate was dissolved in water (30 ml) at pH 7.0
  7. customAfter removal of precipitated materials
  8. washThe column was washed with water
  9. washthe elution
  10. customThe active fractions were collected

Sources & evidence

ORD record
ord-56d7afd659b748aea3eb9fc1c9b38051
Source dataset
uspto-grants-1996_07
Patent number
US05532354

Reaction notes

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