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

HRID 237670ノート

反応式

HRID 237670 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-5bcb0c5e4821451c87051ea4f60e2340
出典データセット
uspto-grants-2014_02
特許番号
US08642585B2

反応ノート

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