Cesium carbonate → HCID 135507537, compound

HRID 494512Notes

Reaction equation

HRID 494512 reaction equation
[CH2:1]([C:5]1([CH3:30])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7]([C:16]2[NH:21][C:20]3[CH:22]=[CH:23][C:24]([OH:26])=[CH:25][C:19]=3[S:18](=[O:28])(=[O:27])[N:17]=2)[C:6]1=[O:29])[CH2:2][CH2:3][CH3:4].Br[CH2:32][C:33]([NH2:35])=[O:34].C(=O)([O-])[O-].[Cs+].[Cs+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.C(OCC)(=O)C>[CH2:1]([C:5]1([CH3:30])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7]([C:16]2[NH:21][C:20]3[CH:22]=[CH:23][C:24]([O:26][CH2:32][C:33]([NH2:35])=[O:34])=[CH:25][C:19]=3[S:18](=[O:28])(=[O:27])[N:17]=2)[C:6]1=[O:29])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 696322-BromoacetamideHCID 136403663HCID 136403663, compound

Product 1

HCID 135507537HCID 135507537, compoundYield 66.9%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Example 27H (0.100 g, 0.235 mmol), 2-bromoacetamide (0.097 g, 0.703 mmol), cesium carbonate (0.382 g, 1.17 mmol), and tetrabutylammonium iodide (0.001 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 (0.076 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-c3d6dca8f0a6480c8292e7f7fdaf4236
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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