HCID 58288264, compound → HCID 58288367, compound

HRID 1476120Notes

Reaction equation

HRID 1476120 reaction equation
C([NH:8][C:9]1[CH:10]=[C:11]([CH2:16][C:17]([CH3:26])([CH3:25])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:12]=[CH:13][C:14]=1[Cl:15])C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[NH2:8][C:9]1[CH:10]=[C:11]([CH2:16][C:17]([CH3:26])([CH3:25])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:12]=[CH:13][C:14]=1[Cl:15]

Participants

4

Reactant 1

HCID 58288264HCID 58288264, compound

Product 1

HCID 58288367HCID 58288367, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2.7 g (about 7.22 mmol) of tert-butyl 3-[3-(benzylamino)-4-chlorophenyl]-2,2-dimethylpropanoate were dissolved in 150 ml of ethyl acetate, and 100 ml of palladium on carbon (10%) were added. The reaction mixture was stirred at RT under an atmosphere of hydrogen at atmospheric pressure overnight. The mixture was then filtered off with suction through kieselguhr, the residue was washed thoroughly with ethyl acetate and the combined filtrate was concentrated. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1→7:1). This gave 1.49 g (72.7% of theory) of the target compound.

Workup

  1. filtrationThe mixture was then filtered off with suction through kieselguhr
  2. washthe residue was washed thoroughly with ethyl acetate
  3. concentrationthe combined filtrate was concentrated
  4. customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1→7:1)

Sources & evidence

ORD record
ord-8a4f14008d564648a5633d8d0b159cc3
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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