Sodium periodate → 2-Chloro-4-{[(2-methylphenyl)methyl][(3S)-5-oxo-1-(2-oxoethyl)-3-pyrrolidinyl]amino}benzonitrile

HRID 1160418Notes

Reaction equation

HRID 1160418 reaction equation
I([O-])(=O)(=O)=O.[Na+].[Cl:7][C:8]1[CH:15]=[C:14]([N:16]([C@H:25]2[CH2:29][C:28](=[O:30])[N:27]([CH2:31][CH:32]([OH:35])CO)[CH2:26]2)[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])[CH:13]=[CH:12][C:9]=1[C:10]#[N:11]>C1COCC1>[Cl:7][C:8]1[CH:15]=[C:14]([N:16]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])[C@H:25]2[CH2:29][C:28](=[O:30])[N:27]([CH2:31][CH:32]=[O:35])[CH2:26]2)[CH:13]=[CH:12][C:9]=1[C:10]#[N:11]

Participants

4

Reactant 2

HCID 23667635Sodium periodateHCID 59516234HCID 59516234, compound

Product 1

HCID 595161812-Chloro-4-{[(2-methylphenyl)methyl][(3S)-5-oxo-1-(2-oxoethyl)-3-pyrrolidinyl]amino}benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An aqueous solution of sodium periodate (0.25 M in H2O, 12.8 mg, 0.06 mmol) was added to a solution of 2-chloro-4-{[(3S)-1-(2,3-dihydroxypropyl)-5-oxo-3-pyrrolidinyl][(2-methylphenyl)methyl]amino}benzonitrile (25.0 mg, 0.06 mmol) in THF. After stirring at room temperature for 30 min, the reaction mixture was extracted three times with ethyl acetate (5 mL). The organics were dried over anhydrous MgSO4 and concentrated to give the titled compound as white foam. The crude material was immediately used in the next step.

Workup

  1. extractionthe reaction mixture was extracted three times with ethyl acetate (5 mL)
  2. dry with materialThe organics were dried over anhydrous MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8a9d174a3f3042e69d51cd035473f8c7
Source dataset
uspto-grants-2010_10
Patent number
US07816395B2

Reaction notes

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