Acetic Acid → 769169-13-3

HRID 1594279Notes

Reaction equation

HRID 1594279 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-cba777340a174a7c8e391cae7f458ade
Source dataset
uspto-grants-2007_11
Patent number
US07300951B2

Reaction notes

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