2-Benzoylcyclohexanone → ethyl (S)-2-(2-benzoylphenylamino)-3-(3'-methylaminobiphenyl-4-yl)propionate

HRID 271843

Reaction equation

HRID 271843 reaction equation
[NH2:1][C@@H:2]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][CH3:22])[CH:16]=2)=[CH:11][CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:23]([CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][C:32]1=O)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1(OC)C=CC=CC=1.[Pd]>[C:23]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[NH:1][C@@H:2]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][CH3:22])[CH:16]=2)=[CH:11][CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 2756272-BenzoylcyclohexanoneHCID 86601617ethyl (S)-2-amino-3-(3'-methylaminobiphenyl-4-yl)propionate

Product 1

HCID 69685584ethyl (S)-2-(2-benzoylphenylamino)-3-(3'-methylaminobiphenyl-4-yl)propionateYield 55.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7519AnisoleSolvent

Procedure

5.7 g (22.1 mmol) of ethyl (S)-2-amino-3-(3′-methylaminobiphenyl-4-yl)propionate and 5.8 g (28.7 mmol) of 2-benzoylcyclohexanone are dissolved in 10 ml of anisole. 0.6 g of 10% palladium-on-charcoal are added and the reaction medium is then refluxed using a Dean-Stark apparatus for 16 h. The cooled reaction medium is filtered through celite, rinsed with ethyl acetate and concentrated. The residue obtained is purified by chromatography on a column of silica and eluted with a 7/3 heptane/ethyl acetate mixture. 5.9 g of desired product are isolated with a 49% yield.

Workup

  1. temperaturethe reaction medium is then refluxed
  2. customfor 16 h
  3. customThe cooled reaction medium
  4. filtrationis filtered through celite
  5. washrinsed with ethyl acetate
  6. concentrationconcentrated
  7. customThe residue obtained
  8. customis purified by chromatography on a column of silica
  9. washeluted with a 7/3 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-5c54cfe186944ee3b0d444c9ffb1752e
Source dataset
uspto-grants-2008_11
Patent number
US07452878B2

Linked notes

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