Sodium Iodide → HCID 14621643, compound

HRID 1639324Notes

Reaction equation

HRID 1639324 reaction equation
Cl[CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[CH:22]([NH:23][CH:24]=[O:25])[C:21](=[O:26])[N:7]2[C:8]=1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)=[O:10].[I-:27].[Na+]>CC(C)=O>[CH:24]([NH:23][CH:22]1[C:21](=[O:26])[N:7]2[C:8]([C:9]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)=[O:10])=[C:3]([CH2:2][I:27])[CH2:4][S:5][C@H:6]12)=[O:25]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 14621685HCID 14621685, compound

Product 1

HCID 14621643HCID 14621643, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

14.5 g (36.6 mM) of p-methoxybenzyl 3-chloromethyl-7-formamido-3-cephem-4-carboxylate was dissolved in 360 ml of acetone. Under cooling with ice, 13.7 g (91.4 mM) of sodium iodide was added to this solution, and the mixture was stirred for 30 minutes, and further at room temperature for 30 minutes. The reaction solution was concentrated under reduced pressure, and the oily residue was dissolved by an addition of ethyl acetate. The organic layer was washed sequentially with water, a saturated sodium thiosulfate aqueous solution and a saturated sodium chloride aqueous solution. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The oily residue was subjected to silica gel column chromatography (Wakogel C-300, eluted with 20% ethyl acetate-chloroform), and the fraction containing the desired product was concentrated to obtain 15.7 g (yield: 87.9%) of p-methoxybenzyl 7-formamido-3-iodomethyl-3-cephem-4-carboxylate.

Workup

  1. additionwas added to this solution
  2. waitfurther at room temperature for 30 minutes
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. dissolutionthe oily residue was dissolved by an addition of ethyl acetate
  5. washThe organic layer was washed sequentially with water
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washThe oily residue was subjected to silica gel column chromatography (Wakogel C-300, eluted with 20% ethyl acetate-chloroform)
  9. additionthe fraction containing the desired product
  10. concentrationwas concentrated

Sources & evidence

ORD record
ord-6f78eb62897f49c88376a5443a5418c4
Source dataset
uspto-grants-1989_11
Patent number
US04883868

Reaction notes

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