1,1'-Carbonyldiimidazole → HCID 69465657, compound

HRID 1597700Notes

Reaction equation

HRID 1597700 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([S:23][CH2:24][C:25]([OH:27])=O)[CH:18]=[CH:19][C:20]=1[O:21][CH3:22].FC(F)(F)C(O)=O.[NH2:35][C@@H:36]1[C:43](=[O:44])[N:42]2[C@@H:37]1[S:38][CH2:39][C:40](/[CH:48]=[C:49]1/[C:50](=[O:62])[N:51]([CH2:54][C:55]3[CH:60]=[CH:59][CH:58]=[C:57]([OH:61])[CH:56]=3)[CH2:52][CH2:53]/1)=[C:41]2[C:45]([OH:47])=[O:46]>CN(C)C(=O)C>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([S:23][CH2:24][C:25]([NH:35][C@@H:36]2[C:43](=[O:44])[N:42]3[C@@H:37]2[S:38][CH2:39][C:40](/[CH:48]=[C:49]2/[C:50](=[O:62])[N:51]([CH2:54][C:55]4[CH:60]=[CH:59][CH:58]=[C:57]([OH:61])[CH:56]=4)[CH2:52][CH2:53]/2)=[C:41]3[C:45]([OH:47])=[O:46])=[O:27])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 72503895735-63-0HCID 69469274HCID 69469274, compound

Product 1

HCID 69465657HCID 69465657, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

With 121.1 mg (0.75 mmol) 1,1,-carbonyldiimidazole, 170.6 mg (0.75 mmol) 2-(3,4-dimethoxyphenylthio)acetic acid and 250.0 mg (0.62 mmol) (E)-(6R,7R)-7-amino-3-[1-(3-hydroxy-benzyl)-2-oxo-pyrrolidin-3-ylidenemethyl]-8-oxo-5-thia- 1-aza-bicyclo[4.2.0]oct-2-ene2-carboxylic acid 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). 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. customThe organic solvent was stripped off at a rotary evaporator
  3. customthe aqueous phase was freeze-dried

Sources & evidence

ORD record
ord-2576676e7d464ccfb9b78c3c9f91d3c7
Source dataset
uspto-grants-2001_09
Patent number
US06294668B1

Reaction notes

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