Sodium Hydroxide → 5-[2-fluoro-4-(2-methoxy-3,5-dimethylpyridin-4-yl)phenyl]-1-[(S)-tetrahydrofuran-3-yl]-1H-pyrazole-4-carboxylic acid

HRID 1043944노트

반응식

HRID 1043944 반응식
[OH-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([C:10]2[C:15]([CH3:16])=[CH:14][N:13]=[C:12]([O:17][CH3:18])[C:11]=2[CH3:19])[CH:7]=[CH:6][C:5]=1[C:20]1[N:24]([C@H:25]2[CH2:29][CH2:28][O:27][CH2:26]2)[N:23]=[CH:22][C:21]=1[C:30]([O:32]CC)=[O:31]>C(O)C>[F:3][C:4]1[CH:9]=[C:8]([C:10]2[C:15]([CH3:16])=[CH:14][N:13]=[C:12]([O:17][CH3:18])[C:11]=2[CH3:19])[CH:7]=[CH:6][C:5]=1[C:20]1[N:24]([C@H:25]2[CH2:29][CH2:28][O:27][CH2:26]2)[N:23]=[CH:22][C:21]=1[C:30]([OH:32])=[O:31]

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 86686373ethyl 5-[2-fluoro-4-(2-methoxy-3,5-dimethylpyridin-4-yl)phenyl]-1-[(S)-tetrahydrofuran-3-yl]-1H-pyrazole-4-carboxylate

생성물 1

HCID 866863755-[2-fluoro-4-(2-methoxy-3,5-dimethylpyridin-4-yl)phenyl]-1-[(S)-tetrahydrofuran-3-yl]-1H-pyrazole-4-carboxylic acid수율 96.4%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
60 °C

실험 절차

A 5 N aqueous sodium hydroxide solution (79 mL) was added to a solution of ethyl 5-[2-fluoro-4-(2-methoxy-3,5-dimethylpyridin-4-yl)phenyl]-1-[(S)-tetrahydrofuran-3-yl]-1H-pyrazole-4-carboxylate (43.2 g) in ethanol (574 mL) at mom temperature, and the reaction mixture was stirred at 60° C. for two hours and 10 minutes. The reaction mixture was cooled to room temperature and then concentrated to half volume under reduced pressure. Water (300 mL) was added to the residue, and ethanol was distilled off under reduced pressure. MTBE (130 mL) was added to the resulting residue, and the aqueous layer was separated. The organic layer was extracted with water (30 mL). The combined aqueous layers were made acidic with 5 N hydrochloric acid (78 mL) under ice-cooling and extracted with ethyl acetate twice. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound (39.0 g).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated to half volume under reduced pressure
  3. additionWater (300 mL) was added to the residue, and ethanol
  4. distillationwas distilled off under reduced pressure
  5. additionMTBE (130 mL) was added to the resulting residue
  6. customthe aqueous layer was separated
  7. extractionThe organic layer was extracted with water (30 mL)
  8. temperaturecooling
  9. extractionextracted with ethyl acetate twice
  10. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-1960ca39c2ff4bd1b5e07c6977276c69
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08563565B2

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