HCID 136360006, compound → HCID 136360009, compound

HRID 1617562Notes

Reaction equation

HRID 1617562 reaction equation
[OH:1][N:2]=[C:3]([C:26]1[CH:31]=[CH:30][N:29]=[C:28]([CH3:32])[CH:27]=1)[CH2:4][CH:5]([C:13]1[CH:18]=[CH:17][C:16]([C:19]#[C:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12]>CO.[Pd]>[OH:1][N:2]=[C:3]([C:26]1[CH:31]=[CH:30][N:29]=[C:28]([CH3:32])[CH:27]=1)[CH2:4][CH:5]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12]

Participants

4

Reactant 1

HCID 136360006HCID 136360006, compound

Product 1

HCID 136360009HCID 136360009, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-{4-[3-[Hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-phenyl}-pent-4-ynoic acid as a mixture of E and Z isomers (4.2:1) (example 84; 50 mg) in methanol (2 mL) was hydrogenated in the presence of Pd (5% on carbon, 6 mg) at room temperature for 5 hours. The solution was filtered over decalite, the filter residue was washed with methanol, and the solution was evaporated. The crude product was purified by flash chromatography on silica gel (gradient CH2Cl2 to CH2Cl2/MeOH 1:1) to yield 5-{4-[3-[hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-phenyl}-pentanoic acid as a mixture of E and Z isomers (4.4:1) as a colorless oil, MS (ESI+): m/z=431.4 ([M+H]+).

Workup

  1. filtrationThe solution was filtered over decalite
  2. washthe filter residue was washed with methanol
  3. customthe solution was evaporated
  4. customThe crude product was purified by flash chromatography on silica gel (gradient CH2Cl2 to CH2Cl2/MeOH 1:1)

Sources & evidence

ORD record
ord-1e82870efef445918330a685e25b4cf7
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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