Sodium Iodide → HCID 13367908, compound

HRID 893758Notes

Reaction equation

HRID 893758 reaction equation
Cl[CH2:2]/[CH:3]=[CH:4]\[C:5]1[CH2:6][S:7][C@@H:8]2[CH:28]([NH:29][C:30](=[O:60])/[C:31](/[C:35]3[N:36]=[C:37]([NH:40][C:41]([C:54]4[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=4)([C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[S:38][CH:39]=3)=[N:32]\[O:33][CH3:34])[C:27](=[O:61])[N:9]2[C:10]=1[C:11]([O:13][CH:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12].[I-:62].[Na+]>CC(C)=O.C(OCC)(=O)C>[I:62][CH2:2]/[CH:3]=[CH:4]/[C:5]1[CH2:6][S:7][C@@H:8]2[CH:28]([NH:29][C:30](=[O:60])/[C:31](/[C:35]3[N:36]=[C:37]([NH:40][C:41]([C:54]4[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=4)([C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[S:38][CH:39]=3)=[N:32]\[O:33][CH3:34])[C:27](=[O:61])[N:9]2[C:10]=1[C:11]([O:13][CH:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 88495627HCID 88495627, compound

Product 1

HCID 13367908HCID 13367908, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of diphenylmethyl 3-[(Z)-3-chloro-1-propen-1-yl]-7-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-methoxyimino-acetamido]-3-cephem-4-carboxylate (IXb) (392 mg, 0.45 mmol) and sodium iodide (204 mg, 1.36 mmol) in acetone (3.9 ml) was stirred at room temperature for 2 hours and diluted with ethyl acetate. The organic solution was successively washed with an aqueous sodium thiosulfate solution, water and brine, dried over anhydrous magnesium sulfate and concentrated to afford 394 mg (91% yield) of the title product.

Workup

  1. washThe organic solution was successively washed with an aqueous sodium thiosulfate solution, water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-55b4e238d1584d4dacf5da7544b8ee35
Source dataset
uspto-grants-1992_06
Patent number
US05126336

Reaction notes

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