Lithium hydroxide, monohydrate → 3-fluoro-4-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenoxy)benzoic acid

HRID 20570노트

반응식

HRID 20570 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[O:13][C:14]1[CH:19]=[C:18]([C:20]([NH:22][C:23]2[CH:27]=[CH:26][N:25]([CH3:28])[N:24]=2)=[O:21])[CH:17]=[C:16]([O:29][C@@H:30]([CH3:33])[CH2:31][OH:32])[CH:15]=1)[C:5]([O:7]CC)=[O:6].O.[OH-].[Li+]>C1COCC1.O>[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[O:13][C:14]1[CH:19]=[C:18]([C:20]([NH:22][C:23]2[CH:27]=[CH:26][N:25]([CH3:28])[N:24]=2)=[O:21])[CH:17]=[C:16]([O:29][C@@H:30]([CH3:33])[CH2:31][OH:32])[CH:15]=1)[C:5]([OH:7])=[O:6]

참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 59346875ethyl 3-fluoro-4-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenoxy)benzoate

생성물 1

HCID 593469353-fluoro-4-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenoxy)benzoic acid수율 95.8%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of ethyl 3-fluoro-4-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenoxy)benzoate (1.8 g, 3.94 mmol) in THF (60 mL) was added to a solution of lithium hydroxide monohydrate (0.83 g, 19.7 mmol) in water (30 mL). The mixture was stirred at RT for 72 hours and the THF removed in vacuo. The aqueous layer was extracted into ethyl acetate (100 mL) to remove any impurities, then acidified with 1M hydrochloric acid and extracted into ethyl acetate (2×100 mL). The combined extracts were dried (MgSO4) and the solvent removed in vacuo to give the desired compound (1.62 g).

후처리

  1. customthe THF removed in vacuo
  2. extractionThe aqueous layer was extracted into ethyl acetate (100 mL)
  3. customto remove any impurities
  4. extractionextracted into ethyl acetate (2×100 mL)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. customthe solvent removed in vacuo

출처 및 근거

ORD 기록
ord-41a5948e1e0b4d4c9514b05e524fd593
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745475B2

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