HCID 68428320, compound → HCID 68430732, compound

HRID 384133Notes

Reaction equation

HRID 384133 reaction equation
[C:1]([O:7][C:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-])=O)[CH:23]=3)=[CH:15][CH:14]=2)[O:10][N:9]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]>C(OCC)(=O)C.[C].[Pd]>[C:1]([O:7][C:8]1[CH:12]=[C:11]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([NH2:28])[CH:23]=3)=[CH:17][CH:18]=2)[O:10][N:9]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 68428320HCID 68428320, compound

Product 1

HCID 68430732HCID 68430732, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(4-(2-(3-nitrophenyl)ethoxy)phenyl)-3-isoxazolyl pivalate (100 mg) in ethyl acetate (5 ml), 13 mg of 10% palladium-carbon catalyst was added, and the reaction solution was stirred at room temperature for 1 hour under hydrogen atmosphere. The catalyst was filtered off through Celite, then the filtrate was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: ethyl acetate/hexane (0:100-25:75-30:70)) to afford the title compound as a yellow oil.

Workup

  1. filtrationThe catalyst was filtered off through Celite
  2. distillationthe filtrate was distilled off under reduced pressure
  3. customthe residue obtained
  4. customwas purified by silica gel column chromatography (eluent: ethyl acetate/hexane (0:100-25:75-30:70))

Sources & evidence

ORD record
ord-b211cc1916f441569dafbd9246ecc8d2
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

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