HCID 67488146, compound → HCID 67486229, compound

HRID 251314Notes

Reaction equation

HRID 251314 reaction equation
[CH3:1][O:2][C:3](=[O:37])[CH2:4][CH2:5][NH:6][C:7](=[O:36])[C:8]1[CH:13]=[CH:12][C:11]([C:14](=[CH:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:28][CH:27]=3)=[CH:22][CH:21]=2)[CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:10][CH:9]=1>[Pd].C(O)C>[CH3:1][O:2][C:3](=[O:37])[CH2:4][CH2:5][NH:6][C:7](=[O:36])[C:8]1[CH:9]=[CH:10][C:11]([CH:14]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]3[CH:27]=[CH:28][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:30][CH:31]=3)=[CH:24][CH:25]=2)[CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 67488146HCID 67488146, compound

Product 1

HCID 67486229HCID 67486229, compoundYield 66.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-{4-[1-(4′-tert-Butyl-biphenyl-4-ylmethylene)-3-methyl-butyl]-benzoylamino}-propionic acid methyl ester (240 mg) is taken into ethanol (20 ml) and 10% Pd/C (20 mg) is added: The system is purged with nitrogen, followed by the introduction of hydrogen (30 psi). The mixture is stirred at room temperature for 4 h, filtered through Celite®, and concentrated. The resulting residue is purified by silica gel column chromatography, eluting with EtOAc/hexanes to afford 160 mg of the titled compound. MS (ES): 500.3 (M++1).

Workup

  1. additionis added
  2. customThe system is purged with nitrogen
  3. filtrationfiltered through Celite®
  4. concentrationconcentrated
  5. customThe resulting residue is purified by silica gel column chromatography
  6. washeluting with EtOAc/hexanes

Sources & evidence

ORD record
ord-28b6c7ce31464b509a73a7ce7291c52b
Source dataset
uspto-grants-2011_01
Patent number
US07863329B2

Reaction notes

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