Tetrahydrofuran → HCID 86583551, compound

HRID 1790576Notes

Reaction equation

HRID 1790576 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:16]2[CH:21]=[C:20]([CH:22]=[CH2:23])[CH:19]=[C:18]([O:24][CH3:25])[CH:17]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1)#[N:2].C1COCC1>CCO.[Pd]>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:16]2[CH:17]=[C:18]([O:24][CH3:25])[CH:19]=[C:20]([CH2:22][CH3:23])[CH:21]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 86583552HCID 86583552, compound

Product 1

HCID 86583551HCID 86583551, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Pd-C (10%, 236 mg, 0.22 mmol) was added a solution of the ethyl (RS)-(4-cyano-phenylamino)-(3-methoxy-5-vinyl-phenyl)-acetate (1.495 g, 4.44 mmol) obtained in Example198.3 in EtOH (40 ml) and THF (4 ml) and the mixture was hydrogenated for 1 h. at room temperature. The reaction mixture was filtered, the filtrate was concentrated and the residue was purified by filtration over SiO2 (eluent: AcOEt/hexane 1:1). There were obtained 1.5 g (99%) of ethyl (RS)-(4-cyano-phenylamino)-(3-ethyl-5-methoxy-phenyl)-acetate as a beige solid; MS: 338 ([M]+).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. filtrationthe residue was purified by filtration over SiO2 (eluent: AcOEt/hexane 1:1)

Sources & evidence

ORD record
ord-cdee9b61f41e40f48a4e847666dd8773
Source dataset
uspto-grants-2006_07
Patent number
US07071212B2

Reaction notes

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