2-Hydroxyisobutyric acid → 3-(4-Bromo-3,5-dimethyl-phenyl)-5-(2-hydroxy-prop-2-yl)-[1,2,4]oxadiazole

HRID 237670Notes

Reaction equation

HRID 237670 reaction equation
F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[OH:23][C:24]([CH3:29])([CH3:28])[C:25](O)=[O:26].C(N(CC)C(C)C)(C)C.[Br:39][C:40]1[C:49]([CH3:50])=[CH:48][C:43]([C:44]([NH:46]O)=[NH:45])=[CH:42][C:41]=1[CH3:51]>CN(C)C=O.O>[Br:39][C:40]1[C:49]([CH3:50])=[CH:48][C:43]([C:44]2[N:45]=[C:25]([C:24]([OH:23])([CH3:29])[CH3:28])[O:26][N:46]=2)=[CH:42][C:41]=1[CH3:51]

Participants

7

Reactant 4

HCID 116712-Hydroxyisobutyric acidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178426651HCID 178426651, compound

Product 1

HCID 866973443-(4-Bromo-3,5-dimethyl-phenyl)-5-(2-hydroxy-prop-2-yl)-[1,2,4]oxadiazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-(Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU; 0.55 g) is added to a solution of 2-hydroxy-isobutyric acid (0.18 g) and N,N-diisopropyl-ethylamine (1.4 mL) in N,N-dimethylformamide (5 mL) at room temperature. The solution is stirred at room temperature for 10 min prior to the addition of 4-bromo-N-hydroxy-3,5-dimethyl-benzamidine (0.40 g). The solution is stirred at room temperature for another 10 min and then at 110° C. overnight. After cooling to room temperature, water is added and the resulting mixture is extracted with ethyl acetate. The combined extract is washed with brine, dried (MgSO4), and concentrated. The residue is chromatographed on reversed phase (HPLC; acetonitrile/water/trifluoroacetic acid) to give the title compound. LC (method 11): tR=1.16 min; Mass spectrum (ESI+): m/z=313/315 (Br) [M+H]+.

Workup

  1. stirringThe solution is stirred at room temperature for another 10 min
  2. customat 110° C.
  3. customovernight
  4. temperatureAfter cooling to room temperature
  5. extractionthe resulting mixture is extracted with ethyl acetate
  6. extractionThe combined extract
  7. washis washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customThe residue is chromatographed on reversed phase (HPLC; acetonitrile/water/trifluoroacetic acid)

Sources & evidence

ORD record
ord-5bcb0c5e4821451c87051ea4f60e2340
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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