1,1'-Carbonyldiimidazole → HCID 86757444, compound

HRID 1597697Notes

Reaction equation

HRID 1597697 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:13][C:14]1[CH:15]=[C:16]([S:21][CH2:22][C:23]([OH:25])=O)[CH:17]=[CH:18][C:19]=1[Cl:20].FC(F)(F)C([O-])=O.[NH2:33][C@@H:34]1[C:41](=[O:42])[N:40]2[C@@H:35]1[S:36][CH2:37][C:38](/[CH:46]=[C:47]1/[C:48](=[O:71])[N:49]([CH2:52][C:53]3[CH:58]=[CH:57][N+:56]([CH2:59][C:60](=[O:70])[NH:61][C:62]4[CH:67]=[CH:66][C:65]([OH:68])=[C:64]([F:69])[CH:63]=4)=[CH:55][CH:54]=3)[CH2:50][CH2:51]/1)=[C:39]2[C:43]([OH:45])=[O:44]>CN(C)C(=O)C>[Cl:13][C:14]1[CH:15]=[C:16]([S:21][CH2:22][C:23]([NH:33][C@@H:34]2[C:41](=[O:42])[N:40]3[C@@H:35]2[S:36][CH2:37][C:38](/[CH:46]=[C:47]2/[C:48](=[O:71])[N:49]([CH2:52][C:53]4[CH:54]=[CH:55][N+:56]([CH2:59][C:60](=[O:70])[NH:61][C:62]5[CH:67]=[CH:66][C:65]([OH:68])=[C:64]([F:69])[CH:63]=5)=[CH:57][CH:58]=4)[CH2:50][CH2:51]/2)=[C:39]3[C:43]([O-:45])=[O:44])=[O:25])[CH:17]=[CH:18][C:19]=1[Cl:20]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 28289932-[(3,4-Dichlorophenyl)thio]acetic acidHCID 87846597HCID 87846597, compound

Product 1

HCID 86757444HCID 86757444, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

With 60.0 mg (0.36 mmol) 1,1′-carbonyldiimidazole, 85.0 mg (0.36 mmol) [(3,4-dichlorophenyl)thio]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: 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-a9d1bbb94d804db3b18f011aabb624d4
Source dataset
uspto-grants-2001_09
Patent number
US06294668B1

Reaction notes

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