Potassium Carbonate → HCID 68898027, compound

HRID 2099725Notes

Reaction equation

HRID 2099725 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][CH:8]([CH3:18])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([OH:17])[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:26]([O:28][C:29](=[O:33])[CH:30](Br)Br)[CH3:27]>CN(C=O)C>[CH2:26]([O:28][C:29]([CH:30]1[O:16][C:13]2[CH:14]=[CH:15][C:10]([CH2:9][CH:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:19])[CH3:18])=[CH:11][C:12]=2[O:17]1)=[O:33])[CH3:27]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69237Ethyl dibromoacetateHCID 67692264HCID 67692264, compound

Product 1

HCID 68898027HCID 68898027, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To 1.30 g (4.6 mmol) of 3C was added 40 ml of anhydrous DMF followed by 2.5 g (18 mmol) of anhydrous K2CO3, 2.5 g of 3 A° molecular sieves and 2.3 mL (17.7 mmol) of ethyldibromoacetate. The reaction mixture was heated at 120° C. for 3 hours under argon atmosphere and concentrated under reduced pressure. To the residue 100 mL of water and 75 mL of ethyl acetate were added and filtered. The filtrate was transferred to a separatory funnel and the organic layer was separated. The aqueous layer was extracted with 4×50 mL of ethyl acetate. All the organic layers were combined, dried (Na2SO4) and concentrated. The residue was purified by silica gel column chromatography using 20% ethyl acetate in hexane to give 413 mg (1.17 mmol, 26%) of 3D as a colorless gum (M+Na, 374).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue 100 mL of water and 75 mL of ethyl acetate were added
  3. filtrationfiltered
  4. customThe filtrate was transferred to a separatory funnel
  5. customthe organic layer was separated
  6. extractionThe aqueous layer was extracted with 4×50 mL of ethyl acetate
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-302e4ebafc9b4e57b2d690ca3d833906
Source dataset
uspto-grants-2009_08
Patent number
US07569676B2

Reaction notes

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