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

HRID 1455584Notes

Reaction equation

HRID 1455584 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.FC(F)(F)C(O)=O>COCCOCCOC.ClCCl>[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

5

Reactant 2

HCID 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-olYield 29.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8150DiglymeSolvent

Procedure

A solution of (3) (1.5 g, 4.3 mmol) in diglyme is heated at 150° C. in a microwave reactor (Smith Creator, S00219) for 40 minutes. Solvent evaporated under vacuum in Genevac Evaporator at 80° C. for 3hours to give a solid. This is taken in dichloromethane (40 mL) and treated with trifluoroacetic acid at room temperature for 2 hours. Solvent evaporated to dryness under reduced pressure, crude taken in water, washed with DCM, aqueous layer basified with 1M NaOH solution and extracted with dichloromethane. Organic layer dried over Na2SO4 and evaporated under reduced pressure to give 2-amino-1-(5-phenyl-[1,2,4]oxadiazol-3-yl)-butan-1-ol (300 mg) as a solid.

Workup

  1. customSolvent evaporated under vacuum in Genevac Evaporator at 80° C. for 3hours
  2. customto give a solid
  3. customSolvent evaporated to dryness under reduced pressure, crude
  4. washwashed with DCM, aqueous layer
  5. extractionextracted with dichloromethane
  6. dry with materialOrganic layer dried over Na2SO4
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-3f2d817630ee4f4a9cde41a309c01e6f
Source dataset
uspto-grants-2009_01
Patent number
US07482448B2

Reaction notes

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