Cesium carbonate → HCID 135507537, compound

HRID 2224834Notes

Reaction equation

HRID 2224834 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-8242f22d13b44160a741afac27b87733
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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