Sodium Iodide → HCID 15671927, compound

HRID 1253244

Reaction equation

HRID 1253244 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:32](=[O:33])[N:13]3[C:14]([C:20]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[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.[I-:34].[Na+].[C:36]([C:39]12[CH2:46][CH2:45][N:42]([CH2:43][CH2:44]1)[CH2:41][CH2:40]2)(=[O:38])[NH2:37]>CC(C)=O>[I-:34].[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:32](=[O:33])[N:13]3[C:14]([C:20]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=4)=[O:21])=[C:15]([CH2:18][N+:42]45[CH2:45][CH2:46][C:39]([C:36](=[O:38])[NH2:37])([CH2:44][CH2:43]4)[CH2:40][CH2:41]5)[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 101300691-azabicyclo[2.2.2]octane-4-carboxamideHCID 10874591(4-Methoxyphenyl)methyl (6R,7R)-3-(chloromethyl)-8-oxo-7-((2-phenylacetyl)amino)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

Product 1

HCID 15671927HCID 15671927, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

p-Methoxybenzyl 7β-phenylacetamido-3-chloromethyl-3-cephem-4-carboxylate (980 mg) was suspended in acetone (20 ml), and sodium iodide (362 mg) was added to the suspension and stirred at room temperature for 1 hour. To the resulting suspension was added 4-carbamoylquinuclidine (313 mg) under ice-cooled condition, and the mixture was stirred for 2 hours. The reaction mixture was filtered, and diethyl ether (70 ml) was added to the filtrate. The deposited solid was filtered to obtain the desired product (500 mg).

Workup

  1. temperaturecooled condition
  2. stirringthe mixture was stirred for 2 hours
  3. filtrationThe reaction mixture was filtered
  4. additiondiethyl ether (70 ml) was added to the filtrate
  5. filtrationThe deposited solid was filtered

Sources & evidence

ORD record
ord-2adfb7a2894947a6ac8716409d2b2423
Source dataset
uspto-grants-1988_05
Patent number
US04748171

Linked notes

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