Lithium Hydroxide → 2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acetic acid

HRID 62053

반응식

HRID 62053 반응식
[F:1][C:2]([F:27])([F:26])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][C:22]([O:24]C)=[O:23])=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.[OH-].[Li+]>O1CCCC1.CO.O>[F:27][C:2]([F:1])([F:26])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][C:22]([OH:24])=[O:23])=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1

참가 물질

6

반응물 2

HCID 3939Lithium HydroxideHCID 90405381methyl 2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acetate

생성물 1

HCID 904042172-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acetic acid수율 98.5%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

In a 100 mL flask, methyl 2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acetate (3.45 g, 9.14 mmol) and lithium hydroxide.hydrate (1.15 g, 27.4 mmol) were diluted with tetrahydrofuran (24.4 mL), methanol (24.4 mL), water (12.2 mL). The reaction was stirred at room temperature for 2 hours. The solvent was evaporated and the resulting solid was diluted with water and adjusted to pH 3 with hydrogen chloride (1 N). The resulting precipitate was extracted with ethyl acetate (5×100 mL). The combined organics were dried over magnesium sulfate, filtered, and concentrated to give the title compound as a white solid (3.27 g, 96%): 1H NMR (400 MHz, DMSO-d6) δ 12.41 (s, 1H), 9.40 (s, 1H), 8.15-8.03 (m, 4H), 7.63 (dq, J=7.9, 1.0 Hz, 2H), 7.49-7.36 (m, 2H), 3.66 (s, 2H), 3.35 (s, 3H); 19F NMR (376 MHz, DMSO-d6) δ −56.98; ESIMS m/z 364 ([M+H]+).

후처리

  1. customThe solvent was evaporated
  2. additionthe resulting solid was diluted with water
  3. extractionThe resulting precipitate was extracted with ethyl acetate (5×100 mL)
  4. dry with materialThe combined organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8de628aad8cd472a84cf4e430d314bd6
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09445594B2

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