Acetic Acid → 769169-13-3

HRID 1985932Notes

Reaction equation

HRID 1985932 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-d527a5cdad5243db92f9a6295f0b2cc8
Source dataset
uspto-grants-2009_06
Patent number
US07547725B2

Reaction notes

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