Trifluoroacetic acid → HCID 22054007, compound

HRID 1765681Notes

Reaction equation

HRID 1765681 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 22054007HCID 22054007, compoundYield 29.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8150DiglymeSolvent

Procedure

A solution of (3) (1.5 g, 4.3 mmol) in diglyme was 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 3 hours to give a brown solid. This was 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 pale brown solid. 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 (2×t, 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 dichloromethane
  6. dry with materialOrganic layer dried over Na2SO4
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-80eb387bc97047c8a0acf1ff0f18676b
Source dataset
uspto-grants-2007_06
Patent number
US07226921B2

Reaction notes

Loading…