HCID 126504123, compound → HCID 90014841, compound

HRID 626434Notes

Reaction equation

HRID 626434 reaction equation
C(OC([NH:11][C@H:12]([C:19]([NH:21][C:22]1[CH:23]=[C:24]([CH2:29][C@@H:30]([CH3:36])[C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:25]=[CH:26][C:27]=1[F:28])=[O:20])[CH:13]([C:15]([F:18])([F:17])[F:16])[CH3:14])=O)C1C=CC=CC=1>C(O)C.C1COCC1.[Pd]>[F:28][C:27]1[CH:26]=[CH:25][C:24]([CH2:29][C@@H:30]([CH3:36])[C:31]([O:33][CH2:34][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

5

Reactant 1

HCID 126504123HCID 126504123, compound

Product 1

HCID 90014841HCID 90014841, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.36 g (4.61 mmol) of ethyl (2R)-3-[3-({N-[(benzyloxy)carbonyl]-4,4,4-trifluorovalyl}amino)-4-fluorophenyl]-2-methylpropanoate (Example 37A, mixture of 4 isomers) were dissolved in a mixture of 9.8 ml of ethanol and 9.8 ml of THF. The solution was inertized with argon, and 293 mg of palladium on carbon (10%) were added. The reaction mixture was stirred vigorously at standard pressure under an atmosphere of hydrogen overnight. Following filtration through kieselguhr and washing with dichloromethane/methanol, the filtrate was concentrated under reduced pressure and the residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1→4:1) and separated. This gave 1.35 g of the target compound as diastereomer mixture 1 (77.2% of theory).

Workup

  1. additionwere added
  2. filtrationfiltration through kieselguhr
  3. washwashing with dichloromethane/methanol
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1→4:1)
  6. customseparated

Sources & evidence

ORD record
ord-7b051e7e62aa4ed1889b6c5ac9807d58
Source dataset
uspto-grants-2016_04
Patent number
US09309198B2

Reaction notes

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