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

HRID 1830148Notes

Reaction equation

HRID 1830148 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>[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

4

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 1

HCID 8150DiglymeSolvent

Procedure

A solution of (3) (1.5 g, 4.3 mmol) in diglyme was heated at 150° C. in a microwave (Smith Creator, S00219) for 40 minutes. Solvent evaporated under vacuum in Genevac Evaporator at 80° C. for 3 hours to give a brown solid. This was taken in dichloromethyl (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 dichloromethyl. Organic layer dried over Na2SO4 to give pale brown solid (300 mg); 1HNMR (CDCl3) 8.14–8.10 (m, 2H), 7.59–7.47 (m, 3H), 4.83 & 4.65 (d, J=5 Hz, 1H), 3.18–3.05 (2m, 1H), 1.71–1.20(m, 2H), 1.05–0.97 (dt, J=7.2 Hz, 3H).

Workup

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

Sources & evidence

ORD record
ord-caf38bb211bb4af7939834fef976ec75
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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