Acetate → HCID 69656156, compound

HRID 1828113Notes

Reaction equation

HRID 1828113 reaction equation
[C:1]([C:3]1[CH:28]=[CH:27][C:6]([CH2:7][NH:8][C:9](=[O:26])[CH:10]([O:23][CH2:24][CH3:25])[N:11]2[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:20][CH3:21])[CH:17]=3)[C:12]2=[O:22])=[C:5](O)[CH:4]=1)#[N:2].[C:30]([O-])(=[O:32])C.ClC[C:36]([NH:38][CH3:39])=[O:37].[I-].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[C:1]([C:3]1[CH:28]=[CH:27][C:6]([CH:7]([O:32][CH3:30])[NH:8][C:9](=[O:26])[CH:10]([O:23][CH2:24][CH3:25])[N:11]2[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:20][CH3:21])[CH:17]=3)[C:12]2=[O:22])=[C:5]([C:36](=[O:37])[NH:38][CH3:39])[CH:4]=1)#[N:2]

Participants

7

Reactant 5

HCID 175AcetateHCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 667732-chloro-N-methylacetamideHCID 22064684HCID 22064684, compound

Product 1

HCID 69656156HCID 69656156, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(RS)-N-(4-Cyano-2-hydroxy-benzyl)-2-ethoxy-2-(5-methoxy-1-oxo-1,3-dihydro-isoindol-2-yl)-acetamide (intermediate of example 64, 101 mg) was dissolved in acetonitrile (2.2 ml) and treated over night under vigorous stirring at 40° C. with 2-chloro-N-methylacetamide (29 mg), potassium iodide (42 mg), and cesium carbonate (92 mg). Pouring onto crashed ice/NH4Cl, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash column chromatography (silica gel, AcOEt), yielded (RS )-N-(4-cyano-2-methylcarbamoyl methoxy-benzyl)-2-ethoxy-2-(5-methoxy-1-oxo-1,3-dihydro-isoindol-2-yl)-acetamide (113 mg), off-white solid, MS 467.4 ([M+H]+).

Workup

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

Sources & evidence

ORD record
ord-d073ce656e4e4e16829cef2d57133b9d
Source dataset
uspto-grants-2006_06
Patent number
US07056932B2

Reaction notes

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