Trifluoroacetic acid → HCID 131715674, compound

HRID 34500Notes

Reaction equation

HRID 34500 reaction equation
FC(F)(F)C([O-])=O.C([NH:27][C:28]1[S:29][CH:30]=[C:31]([C:33](=[N:69][O:70][CH:71]([F:73])[F:72])[C:34]([NH:36][CH:37]2[C:67](=[O:68])[N:39]3[C:40]([C:51]([O:53]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:52])=[C:41]([CH:44]([CH3:50])[NH+:45]4[CH2:49][CH2:48][CH2:47][CH2:46]4)[CH2:42][S:43][C@H:38]23)=[O:35])[N:32]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(OC(C)C)(C)C>C(Cl)Cl>[NH2:27][C:28]1[S:29][CH:30]=[C:31]([C:33](=[N:69][O:70][CH:71]([F:72])[F:73])[C:34]([NH:36][CH:37]2[C:67](=[O:68])[N:39]3[C:40]([C:51]([O-:53])=[O:52])=[C:41]([CH:44]([CH3:50])[NH+:45]4[CH2:49][CH2:48][CH2:47][CH2:46]4)[CH2:42][S:43][C@H:38]23)=[O:35])[N:32]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 7914Diisopropyl EtherHCID 131715676HCID 131715676, compound

Product 1

HCID 131715674HCID 131715674, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of benzhydryl 7-[2-(2-tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-(1-methyl-1-pyrrolidiniomethyl)-3-cephem-4-carboxylate trifluoroacetate (syn isomer) (1.25 g) in methylene chloride (4 ml) was stirred at 0°-5° C., and anisole (2.6 ml) and trifluoroacetic acid (5.2 ml) were added thereto. The mixture was stirred for one hour at 0°-5° C. To the reaction mixture was added diisopropyl ether, and the resultant precipitates were collected by filtration, washed with diisopropyl ether and dissolved in water (400 ml). The solution was subjected to column chromatography on macroporus non-ionic adsorption resin "Diaion HP-20" and the elution was carried out with 30% aqueous solution of methanol. The fractions containing the object compound were collected, concentrated in vacuo and lyophilized to give 7-[2-(2-aminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-(1-methyl-1-pyrrolidiniomethyl)-3-cephem-4-carboxylate (syn isomer) (450 mg).

Workup

  1. customthe resultant precipitates
  2. filtrationwere collected by filtration
  3. washwashed with diisopropyl ether
  4. dissolutiondissolved in water (400 ml)
  5. washthe elution
  6. additionThe fractions containing the object compound
  7. customwere collected
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e23da50c655946a68116796fd287f677
Source dataset
uspto-grants-1988_08
Patent number
US04761410

Reaction notes

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