Sodium Hydroxide → 5-[5-(2,2'-Dimethylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl]-2-hydroxybenzoic acid

HRID 219926노트

반응식

HRID 219926 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:14]=[CH:15][C:16]([OH:23])=[C:17]([CH:22]=3)[C:18]([O:20]C)=[O:19])[N:9]=2)[CH:5]=[CH:4][C:3]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH3:30].[OH-].[Na+]>>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:14]=[CH:15][C:16]([OH:23])=[C:17]([CH:22]=3)[C:18]([OH:20])=[O:19])[N:9]=2)[CH:5]=[CH:4][C:3]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH3:30]

참가 물질

3

반응물 2

HCID 14798Sodium HydroxideHCID 136346390Methyl 5-[5-(2,2'-dimethylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl]-2-hydroxybenzoate

생성물 1

HCID 1358693955-[5-(2,2'-Dimethylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl]-2-hydroxybenzoic acid수율 90%

실험 절차

The title compound was prepared following procedure described for example 4, step 2, but starting from methyl 5-[5-(2,2′-dimethylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl]-2-hydroxybenzoate, obtained in step 1, and using 25 eq. of NaOH at 60° C. for 6 h. Solvents were concentrated and DCM (20 mL) was added. It was washed with HCl 1M. The organic layer was then dried over magnesium sulfate, filtered and concentrated to afford the title compound as a pale orange solid (18 mg; 90%). 1H NMR (DMSO-d6, 300 MHz) δ 8.54 (d, J=2.1 Hz, 1H), 8.22-8.17 (m, 2H), 8.08-8.05 (m, 1H), 7.38-7.28 (m, 4H), 7.19-7.12 (m, 2H), 2.14 (s, 3H), 2.04 (s, 3H). LC/MS (Method A): 385.0 (M−H)−. HPLC (Method A) Rt 5.49 min (Purity: 97.2%).

후처리

  1. customThe title compound was prepared following procedure
  2. customobtained in step 1
  3. customat 60° C.
  4. customfor 6 h
  5. concentrationSolvents were concentrated
  6. additionDCM (20 mL) was added
  7. washIt was washed with HCl 1M
  8. dry with materialThe organic layer was then dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-fe62a9843f1e4905bca6259030284435
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202865B2

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