HCID 58392144, compound → HCID 58392389, compound

HRID 561436Notes

Reaction equation

HRID 561436 reaction equation
[CH3:1][C:2]1(C)OC(=O)[CH:5]([CH:9]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)[C:10]2[C:18]3[C:13](=[C:14]([CH2:19][S:20][CH3:21])[CH:15]=[CH:16][CH:17]=3)[NH:12][CH:11]=2)[C:4](=[O:29])[O:3]1>N1C=CC=CC=1.C(O)C.[Cu]>[CH3:28][C:25]1[CH:26]=[CH:27][C:22]([CH:9]([C:10]2[C:18]3[C:13](=[C:14]([CH2:19][S:20][CH3:21])[CH:15]=[CH:16][CH:17]=3)[NH:12][CH:11]=2)[CH2:5][C:4]([O:3][CH2:2][CH3:1])=[O:29])=[CH:23][CH:24]=1

Participants

5

Reactant 1

HCID 58392144HCID 58392144, compound

Product 1

HCID 58392389HCID 58392389, compoundYield 67.7%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

6.5 mg (102 μmol) of copper powder were added to a solution of 4.34 g of the compound from Example 94A in 75 ml of pyridine and 20 ml of ethanol. The reaction mixture was heated under reflux for 1 h. It was concentrated, and the crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient) to result in 2.55 g of the title compound.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 1 h
  3. concentrationIt was concentrated
  4. customthe crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient)

Sources & evidence

ORD record
ord-1807bf91e6b847499a6fbef6c25ce85c
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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