Sodium Iodide → HCID 131717681, compound

HRID 1681451Notes

Reaction equation

HRID 1681451 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:36](=[O:37])[N:13]3[C:14]([C:20]([O:22][CH:23]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[O:21])=[C:15]([CH2:18]Cl)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].[I-:39].[C:40]1([P:46]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>CC(C)=O>[I-:39].[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:36](=[O:37])[N:13]3[C:14]([C:20]([O:22][CH:23]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[O:21])=[C:15]([CH2:18][P+:46]([C:47]4[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=4)([C:53]4[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=4)[C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 11776TriphenylphosphineHCID 13180403HCID 13180403, compound

Product 1

HCID 131717681HCID 131717681, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

32.5 g (0.0609 mol) of benzhydryl 7-phenylacetamido-3-chloromethyl-3-cephem-4-carboxylate are dissolved in 330 ml of acetone, and 10.1 g (0.0674 mol) of NaI and 17.6 g (0.0671 mol) of triphenylphosphine are added in succession, with stirring. After the mixture has been stirred at room temperature for 1.5 hours, the insoluble material is removed by filtration with suction and the clear mother liquor is stirred into 1,000 ml of ether. The white flocculent material which precipitates out is filtered off with suction, washed with 300 ml of ether and dried in vacuo.

Workup

  1. stirringAfter the mixture has been stirred at room temperature for 1.5 hours
  2. customthe insoluble material is removed by filtration with suction
  3. stirringthe clear mother liquor is stirred into 1,000 ml of ether
  4. customThe white flocculent material which precipitates out
  5. filtrationis filtered off with suction
  6. washwashed with 300 ml of ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-6252bf9a9c7244bfbb1437ee5fdc2fbf
Source dataset
uspto-grants-1992_12
Patent number
US05171854

Reaction notes

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