Cesium carbonate → HCID 15391008, compound

HRID 342148Notes

Reaction equation

HRID 342148 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:23][C:24]#[C:25][CH3:26])[CH2:10][N:11]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=1)[C:12](=[O:15])[CH2:13]Cl)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].CCOC(C)=O.CCCCCC>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH:9]([CH2:23][C:24]#[C:25][CH3:26])[CH2:10][N:11]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)[C:12](=[O:15])[CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 21226206Ethyl acetate hexaneHCID 67590094HCID 67590094, compound

Product 1

HCID 15391008HCID 15391008, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the chloroacetamide from Step H (1.68 g, 4.23 mmol) in 15 mL of dry DMF at 0° C. was added Cs2CO3 (3.08 g, 9.48 mmol). The solution was stirred for 30 minutes, then allowed to warm to room temperature. After 14 hours, the reaction was poured into 50% EtOAc/hexane, washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide the crude product. This material was purified by silica gel chromatography (20-40% EtOAc/hexane) to yield the titled product.

Workup

  1. waitAfter 14 hours
  2. washwashed with water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide the crude product
  7. customThis material was purified by silica gel chromatography (20-40% EtOAc/hexane)

Sources & evidence

ORD record
ord-46c18d178c2541e8b18636d55092ba8b
Source dataset
uspto-grants-1999_01
Patent number
US05856326

Reaction notes

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