HCID 118106777, compound → HCID 131735219, compound

HRID 626432Notes

Reaction equation

HRID 626432 reaction equation
C(OC([NH:11][C@H:12]([C:19]([NH:21][C:22]1[CH:23]=[C:24]([CH2:29][CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH:25]=[CH:26][C:27]=1[Cl:28])=[O:20])[CH:13]([C:15]([F:18])([F:17])[F:16])[CH3:14])=O)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[Cl:28][C:27]1[CH:26]=[CH:25][C:24]([CH2:29][CH2:30][C:31]([O:33][C:34]([CH3:36])([CH3:37])[CH3:35])=[O:32])=[CH:23][C:22]=1[NH:21][C:19](=[O:20])[C@H:12]([CH:13]([C:15]([F:18])([F:17])[F:16])[CH3:14])[NH2:11]

Participants

4

Reactant 1

HCID 118106777HCID 118106777, compound

Product 1

HCID 131735219HCID 131735219, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3.19 g (5.87 mmol) of tert-butyl 3-[3-({N-[(benzyloxy)carbonyl]-4,4,4-trifluorovalyl}amino)-4-chlorophenyl]propanoate (Example 34A, racemic diastereomer mixture) were dissolved in 50 ml of ethyl acetate. The solution was inertized with argon, and 125 mg of palladium on carbon (5%) were added. The reaction mixture was stirred vigorously at standard pressure under an atmosphere of hydrogen for 3 h. After filtration through kieselguhr, the filtrate was concentrated under reduced pressure. The residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 50:1→3:1) and the diastereomers were separated:

Workup

  1. additionwere added
  2. filtrationAfter filtration through kieselguhr
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 50:1→3:1)
  5. customthe diastereomers were separated

Sources & evidence

ORD record
ord-31eaf78dedff4b85b49045dde48754c2
Source dataset
uspto-grants-2016_04
Patent number
US09309198B2

Reaction notes

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