Cesium carbonate → HCID 66922405, compound

HRID 2039869Notes

Reaction equation

HRID 2039869 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:20]3=N[CH:22]=[C:23]([OH:25])[CH:24]=[C:19]3[N:18]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:17]=2[O:32][C:33]2[C:38]([CH3:39])=[CH:37][CH:36]=[CH:35][C:34]=2[CH3:40])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:41](=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:48][C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50]>CN(C=O)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]([C:16]2[C:20]3[C:19](=[CH:24][C:23]([O:25][CH2:48][C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])=[CH:22][CH:41]=3)[N:18]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:17]=2[O:32][C:33]2[C:38]([CH3:39])=[CH:37][CH:36]=[CH:35][C:34]=2[CH3:40])=[O:15])[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 58149440HCID 58149440, compound

Product 1

HCID 66922405HCID 66922405, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The compound of example 56 (60 mg, 111 μmol), cesium carbonate (108 mg, 332 μmol) and tert-butyl bromoacetate (17.9 μl, 23.7 μmol) were stirred in DMF at room temperature for 2 h. The mixture was diluted with water and extracted with EA. The organic layer was dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by silica gel chromatography (EA/HEP). Yield: 67 mg.

Workup

  1. extractionextracted with EA
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (EA/HEP)

Sources & evidence

ORD record
ord-5f4a997ae428430ba48e8e87f3f50c7d
Source dataset
uspto-grants-2013_11
Patent number
US08580813B2

Reaction notes

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