Potassium Carbonate → HCID 22928719, compound

HRID 1352847Notes

Reaction equation

HRID 1352847 reaction equation
[OH:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[CH2:10][N:11]2[CH:15]=[CH:14][CH:13]=[C:12]2[C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)=[O:17])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36].C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:24][C:21]1[CH:20]=[CH:19][C:18]([C:16]([C:12]2[N:11]([CH2:10]/[CH:9]=[CH:8]/[C:4]3[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=3)[O:1][CH2:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:15]=[CH:14][CH:13]=2)=[O:17])=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 516892Sodium BicarbonateHCID 21101200HCID 21101200, compound

Product 1

HCID 22928719HCID 22928719, compoundYield 461.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of the compound (180 mg, 0.567 mmol) of Example 6-2 in N,N-dimethylformamide (3.0 ml) was added potassium carbonate (100 mg, 0.724 mmol) and ethyl 4-bromo-n-bytyrate (105 mg, 0.538 mmol), and the mixture was stirred for 2 hours at 45° C. To the reaction mixture was further added ethyl 4-bromo-n-butyrate (20.0 mg, 0.100 mmol) and the mixture was stirred for additional 9 hours at 50° C. Thereto was added an aqueous sodium hydrogencarbonate solution and the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium chloride solution, and dried over magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified with silica gel chromatography (hexane:ethyl acetate=4:1) to give the subject compound (199 mg, 81%).

Workup

  1. stirringthe mixture was stirred for additional 9 hours at 50° C
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with an aqueous saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was purified with silica gel chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-7706d40b9d6f44c0bc3be2369ebb29f2
Source dataset
uspto-grants-2007_05
Patent number
US07220773B2

Reaction notes

Loading…