Iodoacetamide → HCID 22064659, compound

HRID 1828112Notes

Reaction equation

HRID 1828112 reaction equation
[C:1]([C:3]1[CH:27]=[CH:26][C:6]([CH2:7][NH:8][C:9](=[O:25])[CH:10]([O:22][CH2:23][CH3:24])[N:11]2[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[CH3:20])[C:12]2=[O:21])=[C:5]([OH:28])[CH:4]=1)#[N:2].I[CH2:30][C:31]([NH2:33])=[O:32].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[C:31]([CH2:30][O:28][C:5]1[CH:4]=[C:3]([C:1]#[N:2])[CH:27]=[CH:26][C:6]=1[CH2:7][NH:8][C:9](=[O:25])[CH:10]([O:22][CH2:23][CH3:24])[N:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH3:20])[C:12]1=[O:21])(=[O:32])[NH2:33]

Participants

5

Reactant 3

HCID 3727IodoacetamideHCID 10796Cesium carbonateHCID 22064656HCID 22064656, compound

Product 1

HCID 22064659HCID 22064659, compoundYield 21.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(RS)-N-(4-Cyano-2-hydroxy-benzyl)-2-ethoxy-2-(4-methyl-1-oxo-1,3-dihydro-isoindol-2-yl)-acetamide (300 mg) was dissolved in acetonitrile (10 ml) and treated over night under vigorous stirring at ambient temperature with iodoacetamide (223 mg) and cesium carbonate (411 mg). Pouring onto crushed ice/NH4Cl, twofold extraction with AcOEt, washing with brine, drying over sodium sulfate, and evaporation of the solvents, followed by flash column chromatography (silica gel, AcOEt/MeOH=10/1), afforded 75 mg of (RS)-N-(2-carbamoylmethoxy-4-cyano-benzyl)-2-ethoxy-2-(4-methyl-1-oxo-1,3-dihydro-isoindol-2-yl)-acetamide as white solid, MS 437.4 ([M+H]+).

Workup

  1. additiontreated over night
  2. additionPouring
  3. customonto crushed
  4. extractionice/NH4Cl, twofold extraction with AcOEt
  5. washwashing with brine
  6. dry with materialdrying over sodium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-a05e6cf6aa234864b4b275935d59c852
Source dataset
uspto-grants-2006_06
Patent number
US07056932B2

Reaction notes

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