1,1'-Carbonyldiimidazole → HCID 86757450, compound

HRID 1597701Notes

Reaction equation

HRID 1597701 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[C:17]([Cl:21])=[CH:16][C:15]=1[S:22][CH2:23][C:24]([OH:26])=O.FC(F)(F)C([O-])=O.[NH2:34][C@@H:35]1[C:42](=[O:43])[N:41]2[C@@H:36]1[S:37][CH2:38][C:39](/[CH:47]=[C:48]1/[C:49](=[O:72])[N:50]([CH2:53][C:54]3[CH:59]=[CH:58][N+:57]([CH2:60][C:61](=[O:71])[NH:62][C:63]4[CH:68]=[CH:67][C:66]([OH:69])=[C:65]([F:70])[CH:64]=4)=[CH:56][CH:55]=3)[CH2:51][CH2:52]/1)=[C:40]2[C:44]([OH:46])=[O:45]>CN(C)C(=O)C>[F:70][C:65]1[CH:64]=[C:63]([NH:62][C:61]([CH2:60][N+:57]2[CH:58]=[CH:59][C:54]([CH2:53][N:50]3[CH2:51][CH2:52]/[C:48](=[CH:47]\[C:39]4[CH2:38][S:37][C@H:36]5[N:41]([C:42](=[O:43])[C@H:35]5[NH:34][C:24](=[O:26])[CH2:23][S:22][C:15]5[CH:16]=[C:17]([Cl:21])[C:18]([Cl:20])=[CH:19][C:14]=5[Cl:13])[C:40]=4[C:44]([O-:46])=[O:45])/[C:49]3=[O:72])=[CH:55][CH:56]=2)=[O:71])[CH:68]=[CH:67][C:66]=1[OH:69]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 303740(2,4,5-Trichloro-phenylsulfanyl)-acetic acidHCID 87846597HCID 87846597, compound

Product 1

HCID 86757450HCID 86757450, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

With 60.0 mg (0.36 mmol) 1,1,-carbonyldiimidazole, 99.0 mg (0.36 mmol) (2,4,5-trichloro-phenylsulfanyl)-acetic acid and 200.0 mg (0.30 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: acetonitril (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: acetonitril (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-5430e5fa0814410f98be51201324c918
Source dataset
uspto-grants-2001_09
Patent number
US06294668B1

Reaction notes

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