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 20570ノート

反応式

HRID 20570 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-41a5948e1e0b4d4c9514b05e524fd593
出典データセット
uspto-grants-2010_06
特許番号
US07745475B2

反応ノート

読み込み中…