HCID 67341665, compound → HCID 67341927, compound

HRID 1669322Notes

Reaction equation

HRID 1669322 reaction equation
[CH3:1][O:2][C:3](=[O:40])[CH2:4][CH2:5][NH:6][C:7](=[O:39])[C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:21]2[CH:22]=[C:23]([C:29]3[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=3)[C:24]([O:27][CH3:28])=[CH:25][CH:26]=2)=[CH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:10][CH:9]=1>C(O)C.[Pd]>[CH3:1][O:2][C:3](=[O:40])[CH2:4][CH2:5][NH:6][C:7](=[O:39])[C:8]1[CH:9]=[CH:10][C:11]([CH:14]([C:21]2[CH:22]=[C:23]([C:29]3[CH:30]=[CH:31][C:32]([C:35]([F:36])([F:37])[F:38])=[CH:33][CH:34]=3)[C:24]([O:27][CH3:28])=[CH:25][CH:26]=2)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 67341665HCID 67341665, compound

Product 1

HCID 67341927HCID 67341927, compoundYield 87.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-{4-[1-(6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-hept-1-enyl]-benzoylamino}-propionic acid methyl ester (330 mg) in ethanol (10 mL) is added Pd/C (5%, 20 mg). The system is purged with N2, filled with H2 (30 PSI), stirred at room temperature for 5 h. Then the mixture is filtered through celites, and the filtrate is concentrated to give 3-{4-[1-(6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-heptyl]-benzoylamino}-propionic acid methyl ester (290 mg), hydrolyze by 5N NaOH (0.5 mL) to afford the titled compound. MS (ES): 540.3 [M+H]−.

Workup

  1. customThe system is purged with N2
  2. additionfilled with H2 (30 PSI)
  3. filtrationThen the mixture is filtered through celites
  4. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-6dc8eb41d97e4ac58ec7d054992309bb
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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