Potassium Carbonate → HCID 44819339, compound

HRID 1909641Notes

Reaction equation

HRID 1909641 reaction equation
Cl.[Cl:2][C:3]1[CH:22]=[CH:21][C:6]([O:7][C:8]2[CH:20]=[CH:19][C:11]([O:12][CH2:13][C@@H:14]3[CH2:18][CH2:17][CH2:16][NH:15]3)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34]>CN(C=O)C.O.C(OCC)(=O)C>[CH3:36][O:35][C:33](=[O:34])[CH2:32][CH2:31][CH2:30][N:15]1[CH2:16][CH2:17][CH2:18][C@H:14]1[CH2:13][O:12][C:11]1[CH:19]=[CH:20][C:8]([O:7][C:6]2[CH:21]=[CH:22][C:3]([Cl:2])=[CH:4][CH:5]=2)=[CH:9][CH:10]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 107604Methyl 4-bromobutyrateHCID 66869241HCID 66869241, compound

Product 1

HCID 44819339HCID 44819339, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product from step 4 (3.47 g, 10.2 mmol) in DMF (46.0 mL) was added potassium carbonate (2.85 g, 20.6 mmol) and methyl 4-bromobutyrate (1.48 mL, 12.9 mmol). The resulting suspension was stirred at ambient temperature overnight. The reaction mixture was diluted with water and ethyl acetate. The crude residue was extracted into ethyl acetate. The organic portion was washed with water, washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified by silica gel flash chromatography using hexane/EtOAc (gradient system) to give the title compound (2.30 g, 63%) as a yellow oil.

Workup

  1. extractionThe crude residue was extracted into ethyl acetate
  2. washThe organic portion was washed with water
  3. washwashed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-f5062a6c43024139bf4b0f9f30843757
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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