Sodium Iodide → HCID 14673058, compound

HRID 1639321Notes

Reaction equation

HRID 1639321 reaction equation
[CH:1](=[N:8][CH:9]1[C:30](=[O:31])[N:11]2[C:12]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)=[O:19])=[C:13]([CH2:16]Cl)[CH2:14][S:15][C@H:10]12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-:32].[Na+]>CC(C)=O>[CH:1](=[N:8][CH:9]1[C:30](=[O:31])[N:11]2[C:12]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)=[O:19])=[C:13]([CH2:16][I:32])[CH2:14][S:15][C@H:10]12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 14673056HCID 14673056, compound

Product 1

HCID 14673058HCID 14673058, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

30 g (65.65 mM) of p-methoxybenzyl 7-benzylideneamino-3-chloromethyl-3-cephem-4-carboxylate was dissolved in 500 ml of acetone. Then, 29.5 g (197 mM) of sodium iodide was added thereto, and the mixture was stirred at room temperature for 1 hour. From the reaction solution thus obtained, the solvent was distilled off under reduced pressure. To the residue, 500 ml of ethyl acetate was added. The mixture was washed with a saturated sodium thiosulfate aqueous solution and then with a saturated sodium chloride aqueous solution, then dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure to obtain 27 g (yield: 75%) of p-methoxybenzyl 7-benzylideneamino-3-iodomethyl-3-cephem-4-carboxylate.

Workup

  1. customFrom the reaction solution thus obtained
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionTo the residue, 500 ml of ethyl acetate was added
  4. washThe mixture was washed with a saturated sodium thiosulfate aqueous solution
  5. dry with materialwith a saturated sodium chloride aqueous solution, then dried over anhydrous sodium sulfate
  6. distillationThen, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-59c84a87753342cb990fe96760e9d2e4
Source dataset
uspto-grants-1989_11
Patent number
US04883868

Reaction notes

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