HCID 71184307, compound → (3R)-3-amino-4-(2,4,5-trifluorophenyl)butanoic Acid

HRID 2371010Notes

Reaction equation

HRID 2371010 reaction equation
C([N:8](CC1C=CC=CC=1)[C@H:9]([C:15](=O)[C:16]1[CH:21]=[C:20]([F:22])[C:19]([F:23])=[CH:18][C:17]=1[F:24])[CH2:10][C:11]([O:13]C)=[O:12])C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[NH2:8][C@H:9]([CH2:15][C:16]1[CH:21]=[C:20]([F:22])[C:19]([F:23])=[CH:18][C:17]=1[F:24])[CH2:10][C:11]([OH:13])=[O:12]

Participants

5

Reactant 2

HCID 71184307HCID 71184307, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 7146283(3R)-3-amino-4-(2,4,5-trifluorophenyl)butanoic AcidYield 93.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3 g (S)-methyl 3-(dibenzylamino)-4-oxo-4-(2,4,5-trifluorophenyl)butanoate in 100 ml ethanol, was added 0.5 g of 10% Pd/C under an atmosphere of nitrogen. The atmosphere of nitrogen was replace with an atmosphere of hydrogen, and the reaction was carried out at 25° C. for 5 h. After completion of the reaction, the reaction mixture was filtered through diatomite. The filtrate was concentrated, and the pH was adjusted to 5˜6 by addition of 10% hydrochloric acid. The aqueous layer was washed with ethyl acetate, and then concentrated to obtain 1.47 g (R)-3-amino-4-(2,4,5-trifluorophenyl)butanoic acid as white solid, with a yield of 93.2%.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered through diatomite
  3. concentrationThe filtrate was concentrated
  4. additionthe pH was adjusted to 5˜6 by addition of 10% hydrochloric acid
  5. washThe aqueous layer was washed with ethyl acetate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-de50ab816e0c4d68989df5f69d129144
Source dataset
uspto-grants-2014_04
Patent number
US08710255B2

Reaction notes

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