Sodium Hydroxide → AZD 8329

HRID 1799372노트

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HRID 1799372 반응식
[OH-].[Na+].[CH:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH:4]1[NH:13][C:14]([C:16]1[CH:17]=[N:18][N:19]([C:25]3[CH:34]=[CH:33][C:28]([C:29]([O:31]C)=[O:30])=[CH:27][CH:26]=3)[C:20]=1[C:21]([CH3:24])([CH3:23])[CH3:22])=[O:15])[CH2:10]2>CO>[CH:3]12[CH2:10][CH:9]3[CH2:8][CH:7]([CH2:6][CH:5]([CH2:11]3)[CH:4]1[NH:13][C:14]([C:16]1[CH:17]=[N:18][N:19]([C:25]3[CH:34]=[CH:33][C:28]([C:29]([OH:31])=[O:30])=[CH:27][CH:26]=3)[C:20]=1[C:21]([CH3:23])([CH3:24])[CH3:22])=[O:15])[CH2:12]2

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 59516081HCID 59516081, 화합물2회

생성물 1

HCID 25006684AZD 8329수율 89.3%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
70 °C

실험 절차

2M aqueous sodium hydroxide solution (51.7 mL, 103.32 mmol) was added to methyl 4-[4-(2-adamantylcarbamoyl)-5-tert-butyl-pyrazol-1-yl]benzoate (Intermediate #56) (4.5 g, 10.33 mmol) in methanol (100 mL). The mixture was stirred at 70° C. for 1 hour and then cooled to ambient temperature, concentrated under reduced pressure and diluted with water (100 mL). The reaction mixture was adjusted to pH 3 with 2M HCl. The reaction mixture was extracted with EtOAc (500 mL) and washed to sequentially with water (2×100 mL), and saturated brine (50 mL). The organic layer was dried over MgSO4, filtered and evaporated to give a pale yellow solid. The solid was washed with EtOAc (20 mL), collected by filtration and dried under vacuum to give 4-[4-(2-adamantylcarbamoyl)-5-tert-butyl-pyrazol-1-yl]benzoic acid (3.89 g, 89%) as a cream crystalline solid.

후처리

  1. temperaturecooled to ambient temperature
  2. concentrationconcentrated under reduced pressure
  3. additiondiluted with water (100 mL)
  4. extractionThe reaction mixture was extracted with EtOAc (500 mL)
  5. washwashed to sequentially with water (2×100 mL), and saturated brine (50 mL)
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customto give a pale yellow solid
  10. washThe solid was washed with EtOAc (20 mL)
  11. filtrationcollected by filtration
  12. customdried under vacuum

출처 및 근거

ORD 기록
ord-5ded6b6b10b54e39b396048a5d488c9b
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08344016B2

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