HCID 86717927, compound → 1609346-06-6

HRID 1486260Notes

Reaction equation

HRID 1486260 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]([NH:14]C(C1C=CC=CC=1)CO)([CH3:13])[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9]>C(O)C.[OH-].[Pd+2].[OH-]>[NH2:14][C:3]([CH3:13])([C:2]([F:1])([F:24])[F:25])[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:9])[CH3:10]

Participants

4

Reactant 1

HCID 86717927HCID 86717927, compound

Product 1

HCID 901360511609346-06-6

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

39 g (107.6 mmol) of tert-butyl-{3,3,3-trifluoro-2-[(2-hydroxy-1-phenylethyl)amino]-2-methylpropyl}carbamate from Example 50A were initially charged under argon in ethanol (700 ml), and 5.44 g (53.8 mmol) of palladium(II) hydroxide (20% on activated carbon, water-moist, about 60%) were added. The reaction mixture was hydrogenated at standard pressure for 16 h. Then the reaction mixture was filtered through silica gel and concentrated. The residue was purified by means of silica gel chromatography (cyclohexane/ethyl acetate gradient: 9/1 to 6/4). This gave 15.8 g (61% of theory) of the target compound.

Workup

  1. filtrationThen the reaction mixture was filtered through silica gel
  2. concentrationconcentrated
  3. customThe residue was purified by means of silica gel chromatography (cyclohexane/ethyl acetate gradient: 9/1 to 6/4)

Sources & evidence

ORD record
ord-b9f407fbfb5e43e3bab34685d1cc59f6
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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