Cesium carbonate → HCID 15063396, compound

HRID 641703Notes

Reaction equation

HRID 641703 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13].Br[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CC(C)=O>[C:22]([O:21][C:19](=[O:20])[CH2:18][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 15063395HCID 15063395, compound

Product 1

HCID 15063396HCID 15063396, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the product of Step 2 (20 g) in 300 mL of DMF was added 30 g of BrCH2CO2-t-Bu and 65 g of Cs2CO3. The reaction mixture was stirred at 60° C. for 24 h, and was then diluted with 300 ml of acetone and filtered. The filtrate was concentrated and the residue was purified by silica gel chromatography eluted with 1:2 EtOAc/hexane to give 30 g of the title compound as a syrup.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified by silica gel chromatography
  4. washeluted with 1:2 EtOAc/hexane

Sources & evidence

ORD record
ord-842c9aa114e34eae863e7920d371edb9
Source dataset
uspto-grants-2010_04
Patent number
US07696222B2

Reaction notes

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