Cesium carbonate → HCID 135518347, compound

HRID 494517Notes

Reaction equation

HRID 494517 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH3:17])([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[C:4](=[O:18])[C:3]=1[C:19]1[NH:24][C:23]2[CH:25]=[CH:26][C:27]([OH:29])=[CH:28][C:22]=2[S:21](=[O:31])(=[O:30])[N:20]=1.Br[CH2:33][C:34]([NH2:36])=[O:35].C(=O)([O-])[O-].[Cs+].[Cs+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.C(OCC)(=O)C>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH3:17])([CH2:12][CH2:13][CH:14]([CH3:15])[CH3:16])[C:4](=[O:18])[C:3]=1[C:19]1[NH:24][C:23]2[CH:25]=[CH:26][C:27]([O:29][CH2:33][C:34]([NH2:36])=[O:35])=[CH:28][C:22]=2[S:21](=[O:30])(=[O:31])[N:20]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 696322-BromoacetamideHCID 136403632HCID 136403632, compound

Product 1

HCID 135518347HCID 135518347, compoundYield 87.7%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Example 28H (0.100 g, 0.227 mmol), 2-bromoacetamide (0.124 g, 0.681 mmol), cesium carbonate (0.390 g, 1.14 mmol), and tetrabutylammonium iodide (0.011 g, 0.024 mmol) in dimethylformamide (2.5 mL) was stirred at 25° C. for 72 hours. The mixture was diluted with ethyl acetate, washed with water and brine, dried with sodium sulfate, filtered, and concentrated in vacuo to give the free acid (0.099 g).

Workup

  1. washwashed with water and brine
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-69921864a5f245d198f0873a04098c4e
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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