Ethyl Acetate → HCID 15428589, compound

HRID 1421690Notes

Reaction equation

HRID 1421690 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([NH:8][C:9]1[CH:23]=[CH:22][C:12]([CH2:13][O:14][C:15](=[O:21])[CH2:16][CH2:17][CH2:18][CH2:19][Br:20])=[CH:11][CH:10]=1)=[O:7].C([O-])([O-])=O.[Cs+].[Cs+].CCOC(C)=O>CN(C=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[O:7]=[C:6]1[CH2:5][CH2:4][CH2:3][CH2:2][N:8]1[C:9]1[CH:23]=[CH:22][C:12]([CH2:13][O:14][C:15](=[O:21])[CH2:16][CH2:17][CH2:18][CH2:19][Br:20])=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 10796Cesium carbonate2×HCID 15428588HCID 15428588, compound

Product 1

HCID 15428589HCID 15428589, compound

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

The ester from Step 1 (1 g, 2.22 mmol) was dissolved in DMF. Cs2CO3 (725 mg , 2.22 mmol) was added and the reaction mixture was heated to 50° for 18 hours. TLC shows ~50% starting material remaining. Additional Cs2CO3 (2.22 mmol) was added the reaction mixture was heated at 50° for and additional 8 hours. The mixture was dissolved in 10% citric acid and extracted with EtOAc. The organic layer was washed with saturated NaHCO3, H2O and brine, dried (MgSO4) filtered and concentrated to yield a yellow oil. Flash chromatography (EtOAc) yielded the title compound as a yellow oil.

Workup

  1. temperaturethe reaction mixture was heated to 50° for 18 hours
  2. temperaturewas heated at 50° for and additional 8 hours
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with saturated NaHCO3, H2O and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield a yellow oil

Sources & evidence

ORD record
ord-a9a1b58203264fe9a94c64a2c214e0f3
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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