Sodium Iodide → HCID 67901183, compound

HRID 1885142Notes

Reaction equation

HRID 1885142 reaction equation
[I-:1].[Na+].[C:3]([O:7][C:8]([NH:10][CH:11]1[C:38](=[O:39])[N:13]2[C:14]([C:22]([O:24][CH:25]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])=[C:15](/[CH:18]=[CH:19]\[CH2:20]Cl)[CH2:16][S:17][C@H:12]12)=[O:9])([CH3:6])([CH3:5])[CH3:4]>CC(C)=O>[C:3]([O:7][C:8]([NH:10][CH:11]1[C:38](=[O:39])[N:13]2[C:14]([C:22]([O:24][CH:25]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])=[C:15](/[CH:18]=[CH:19]/[CH2:20][I:1])[CH2:16][S:17][C@H:12]12)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 67901180HCID 67901180, compound

Product 1

HCID 67901183HCID 67901183, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To an ice cooled solution of sodium iodide (900 mg, 6 mmol) in acetone was added a solution of diphenylmethyl 7-t-butoxycarbonylamino-3-[(Z)-3-chloro-1-propen-1-yl]-3-cephem-4-carboxylate (VIa) (1.08 g, 2 mmol) in acetone (2.5 ml). The mixture was stirred while being cooled in an ice bath for 3.5 hours, and was concentrated under reduced pressure. The residue was diluted with ethyl acetate and aqueous sodium thiosulfate solution. The organic layer was separated, dried over magnesium sulfate, and concentrated. 923mg of the title product was obtained as a yellow powder after crystallization from a small volume of ethanol (73% yield).

Workup

  1. temperaturewhile being cooled in an ice bath for 3.5 hours
  2. concentrationwas concentrated under reduced pressure
  3. additionThe residue was diluted with ethyl acetate and aqueous sodium thiosulfate solution
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c0772bb307294f34b8b6e7aeabf923b0
Source dataset
uspto-grants-1992_09
Patent number
US05143911

Reaction notes

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