{4-[2-(Pyrid-3-yl)ethenyl]-2-phenylbenzoyl}methionine methyl ester → {4-[2-(Pyrid-3-yl)ethyl]-2-phenylbenzoyl}methionine methyl ester

HRID 2121189Notes

Reaction equation

HRID 2121189 reaction equation
[CH3:1][O:2][C:3](=[O:32])[C@H:4]([CH2:28][CH2:29][S:30][CH3:31])[NH:5][C:6](=[O:27])[C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[CH:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:9][C:8]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:32])[C@H:4]([CH2:28][CH2:29][S:30][CH3:31])[NH:5][C:6](=[O:27])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:9][C:8]=1[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 1

HCID 54096885{4-[2-(Pyrid-3-yl)ethenyl]-2-phenylbenzoyl}methionine methyl ester

Product 1

HCID 20622784{4-[2-(Pyrid-3-yl)ethyl]-2-phenylbenzoyl}methionine methyl esterYield 71.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of the {4-[2-(pyrid-3-yl)ethenyl]-2-phenylbenzoyl}methionine methyl ester prepared in Example 210 (160 mg, 0.36 mmol) and palladium (10%) on carbon (460 mg, 0.43 mmol of palladium) in methanol was flushed with hydrogen, and stirred under a positive hydrogen pressure for 8 hours. The mixture was then filtered through Celite, rinsed with ethyl acetate, and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate) give {4-[2-(pyrid-3-yl)ethyl]-2-phenylbenzoyl}methionine methyl ester (115 mg, 71%). 1H NMR (300 MHz, CDCl3) δ 8.45 (m, 2H), 7.64 (d, 1H), 7.40 (m, 7H), 7.22 (dd, 2H), 7.10 (d, 1H), 5.87 (br d, 1H), 4.68 (m, 1H), 3.67 (s, 3H), 2.99 (m, 4H), 2.08 (m, 2H), 2.02 (s, 3H), 1.93 (m, 1H), 1.76 (m, 1H). MS (APCI+) m/e 449 (M+H)+.

Workup

  1. customwas flushed with hydrogen
  2. filtrationThe mixture was then filtered through Celite
  3. washrinsed with ethyl acetate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-2730954fc7c24bff9f9499526d8dc299
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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