HCID 58392355, compound → HCID 58392206, compound

HRID 561392Notes

Reaction equation

HRID 561392 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[C:27]3[C:22](=[C:23]([CH2:28][S:29][CH3:30])[CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)[CH:9]2C(=O)O[C:12](C)([CH3:16])[O:11][C:10]2=[O:18])=[CH:4][CH:3]=1>N1C=CC=CC=1.C(O)C.[Cu]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:19]2[C:27]3[C:22](=[C:23]([CH2:28][S:29][CH3:30])[CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)[CH2:9][C:10]([O:11][CH2:12][CH3:16])=[O:18])=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 58392355HCID 58392355, compound

Product 1

HCID 58392206HCID 58392206, compound

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

18 mg (0.28 mmol) of copper powder were added to 12.2 g (27.5 mmol) of the compound from Example 13A in 200 ml of pyridine and 55 ml of ethanol. The reaction mixture was heated under reflux for 4 h. It was concentrated, and the residue was taken up in dichloromethane, washed with water, 1N hydrochloric acid and saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient). 6.68 g (56% of theory) of the target compound were obtained.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 4 h
  3. concentrationIt was concentrated
  4. washwashed with water, 1N hydrochloric acid and saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient)
  9. custom6.68 g (56% of theory) of the target compound were obtained

Sources & evidence

ORD record
ord-55d35807f9f24c6aaa3bd797bcc94395
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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