Acetic Acid → 769169-13-3

HRID 2266876Notes

Reaction equation

HRID 2266876 reaction equation
[N:1]([C@@H:4]([C@H:8]([CH3:14])[CH2:9][C:10]([F:13])([F:12])[F:11])[C:5]([OH:7])=[O:6])=[N+]=[N-].C(O)(=O)C>[Pd].O>[F:11][C:10]([F:12])([F:13])[CH2:9][C@@H:8]([CH3:14])[C@@H:4]([C:5]([OH:7])=[O:6])[NH2:1]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86594488HCID 86594488, compound

Product 1

HCID 86594487769169-13-3Yield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

(2S,3R)-2-azido-5,5,5-trifluoro-3-methylpentanoic acid (3.2 g, 17.27 mmol), 10% palladium on carbon (0.79 g), glacial acetic acid (37 mL) and water (90 mL) was placed under an atmosphere of hydrogen (40 psi) and shaken on Parr hydrogenator. After 20 h, the reaction mixture was filtered through a pad of the Celite® reagent which was rinsed well with H2O (20 mL). The filtrate was concentrated under reduced pressure to produce a white solid. The solid was triturated with EtOAc (200 mL), filtered and washed once more with EtOAc (200 mL) then air dried to give 5,5,5-trifluoro-L-alloisoleucine as a white solid (2.7 g, 96%). Mass Spectrum (−ESI): 184 (M−H)−.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of the Celite® reagent which
  2. washwas rinsed well with H2O (20 mL)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customto produce a white solid
  5. customThe solid was triturated with EtOAc (200 mL)
  6. filtrationfiltered
  7. washwashed once more with EtOAc (200 mL)
  8. customair dried

Sources & evidence

ORD record
ord-c9da60ddcda14a45b557e1cd0640122a
Source dataset
uspto-grants-2010_12
Patent number
US07858658B2

Reaction notes

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