Potassium Carbonate → HCID 86622677, compound

HRID 1946614Notes

Reaction equation

HRID 1946614 reaction equation
[C:1]1([C:7]2[C:8]3[CH:18]=[CH:17][CH:16]=[CH:15][C:9]=3[NH:10][C:11](=[O:14])[CH2:12][N:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[O:14]=[C:11]1[N:10]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:9]2[CH:15]=[CH:16][CH:17]=[CH:18][C:8]=2[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:13][CH2:12]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76175RO-05-2921HCID 117544Ethyl 6-bromohexanoate

Product 1

HCID 86622677HCID 86622677, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Title compound 362 (400 mg, 1.69 mmol), ethyl 6-bromohexanoate (0.3 mL, 1.69 mmol) and potassium carbonate (584 mg, 4.23 mmol) were mixed in DMF (20 mL) and the reaction mixture was heated to 80 oC for 24 hours. The DMF was removed and the residue was partitioned between water and ethyl acetate. The 2 layers were split and the aqueous layer was extracted with 2 other portions of ethyl acetate. The combined organic layers were washed with brine, dried, filtered and evaporated. The crude product was purified by flash chromatography (2:1 to 1:2, hexanes:ethyl acetate) to afford title compound 363 (400 mg, 63%) as a clear oil.

Workup

  1. temperaturethe reaction mixture was heated to 80 oC for 24 hours
  2. customThe DMF was removed
  3. customthe residue was partitioned between water and ethyl acetate
  4. customThe 2 layers were split
  5. extractionthe aqueous layer was extracted with 2 other portions of ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe crude product was purified by flash chromatography (2:1 to 1:2, hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-7459e59f738d4246888ef25bede65c6d
Source dataset
uspto-grants-2013_03
Patent number
US08399452B2

Reaction notes

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