1,1'-Carbonyldiimidazole → HCID 86757447, compound

HRID 1597699Notes

Reaction equation

HRID 1597699 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=[O:2].FC(F)(F)C1C=C[C:18]([C:21]2[CH:25]=[CH:24][S:23][C:22]=2[CH2:26][C:27](O)=O)=CC=1.[F:32][C:33]([F:38])([F:37])[C:34]([O-])=O.[NH2:39][C@@H:40]1[C:47](=[O:48])[N:46]2[C@@H:41]1[S:42][CH2:43][C:44](/[CH:52]=[C:53]1/[C:54](=[O:77])[N:55]([CH2:58][C:59]3[CH:64]=[CH:63][N+:62]([CH2:65][C:66](=[O:76])[NH:67][C:68]4[CH:73]=[CH:72][C:71]([OH:74])=[C:70]([F:75])[CH:69]=4)=[CH:61][CH:60]=3)[CH2:56][CH2:57]/1)=[C:45]2[C:49]([OH:51])=[O:50]>CN(C)C(=O)C>[F:75][C:70]1[CH:69]=[C:68]([NH:67][C:66]([CH2:65][N+:62]2[CH:61]=[CH:60][C:59]([CH2:58][N:55]3[CH2:56][CH2:57]/[C:53](=[CH:52]\[C:44]4[CH2:43][S:42][C@H:41]5[N:46]([C:47](=[O:48])[C@H:40]5[NH:39][C:25](=[O:2])[CH2:24][S:23][C:22]5[CH:26]=[CH:27][C:34]([C:33]([F:38])([F:37])[F:32])=[CH:18][CH:21]=5)[C:45]=4[C:49]([O-:51])=[O:50])/[C:54]3=[O:77])=[CH:64][CH:63]=2)=[O:76])[CH:73]=[CH:72][C:71]=1[OH:74]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 86757449HCID 86757449, compoundHCID 87846597HCID 87846597, compound

Product 1

HCID 86757447HCID 86757447, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

With 66.8 mg (0.41 mmol) 1,1, -carbonyldiimidazole, 97.3 mg (0.41 mmol) 2-[4-(trifluoromethyl)phenylthiolacetic acid and 250.0 mg (0.37 mmol) (E)-(6R,7R)-7-amino-3-[1-[1-[(3-fluoro-4-hydroxy-phenylcarbamoyl)-methyl]-pyridin-1-ium-4-ylmethyl]-2-oxo-pyrrolidin-3-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate trifluoroacetate in 4 ml N,N-dimethylacetamide. The resulting solid was purified by column chromatography on MCI gel (75-150μ, Mitsubishi Kasei Corporation) with a gradient of water:acetonitrile (1:0, 4:1, 3:1, 2:1, 1:1). The organic solvent was stripped off at a rotary evaporator and the aqueous phase was freeze-dried.

Workup

  1. customThe resulting solid was purified by column chromatography on MCI gel (75-150μ, Mitsubishi Kasei Corporation) with a gradient of water:acetonitrile (1:0, 4:1, 3:1, 2:1, 1:1)
  2. customThe organic solvent was stripped off at a rotary evaporator
  3. customthe aqueous phase was freeze-dried

Sources & evidence

ORD record
ord-f2751f9971084d7b83818b9d2eefdddb
Source dataset
uspto-grants-2001_09
Patent number
US06294668B1

Reaction notes

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