Water → 2-Amino-1-(5-phenyl-[1,2,4]oxadiazol-3-yl)-butan-1-ol

HRID 1830162Notes

Reaction equation

HRID 1830162 reaction equation
C(OC(=O)[NH:7][CH:8]([CH:11]([OH:24])[C:12](=[NH:23])[NH:13][O:14][C:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:9][CH3:10])(C)(C)C.O.C(O)(C(F)(F)F)=O>C(O)C.[OH-].[OH-].[Pd+2]>[NH2:7][CH:8]([CH2:9][CH3:10])[CH:11]([C:12]1[N:23]=[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:14][N:13]=1)[OH:24]

Participants

6

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 178458006[(Z)-[1-amino-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]pentylidene]amino] benzoate

Product 1

HCID 220540072-Amino-1-(5-phenyl-[1,2,4]oxadiazol-3-yl)-butan-1-ol

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Compound 3 (9.0 g, 39 mmol) was dissolved in ethanol (100 ml) and water (20 ml) followed by the addition of 9 grams of Pd(OH)2 and TFA (4 ml). The mixture was hydrogenated at 50 psi for 48 hours, then the reaction was filtered through celite which was concentrated to give 9 grams of crude material 4 which was used without further purification. Compound 4 was dissolved in dry methanol (300 ml) and HCl gas was bubbled through for 15 minutes. The reaction was stirred at room temperature for three days and was concentrated. The crude product was purified on silica eluting With 1:1 heptane/ethyl acetate to give 3.9 grains of compound 5.

Workup

  1. filtrationthe reaction was filtered through celite which
  2. concentrationwas concentrated
  3. customto give 9 grams of crude material 4 which
  4. customwas used without further purification
  5. dissolutionCompound 4 was dissolved in dry methanol (300 ml)
  6. customHCl gas was bubbled through for 15 minutes
  7. concentrationwas concentrated
  8. customThe crude product was purified on silica eluting With 1:1 heptane/ethyl acetate

Sources & evidence

ORD record
ord-5c92a633c8ee46439903bf317ed770f1
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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