Lithium hydroxide, monohydrate → (R)-2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxylic acid

HRID 59887

反応式

HRID 59887 の反応式
[CH2:1]([O:3][C:4]1[CH:27]=[CH:26][CH:25]=[CH:24][C:5]=1[O:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]2[N:18]=[CH:17][C:16]([C:19]([O:21]CC)=[O:20])=[CH:15][N:14]=2)[CH2:8]1)[CH3:2].O[Li].O>C1COCC1.O>[CH2:1]([O:3][C:4]1[CH:27]=[CH:26][CH:25]=[CH:24][C:5]=1[O:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]2[N:18]=[CH:17][C:16]([C:19]([OH:21])=[O:20])=[CH:15][N:14]=2)[CH2:8]1)[CH3:2]

参加物

4

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 131737069ethyl (R)-2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxylate

生成物 1

HCID 118366221(R)-2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxylic acid収率 78.5%

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

反応条件

温度
22.5 °C

実験手順

To a solution of ethyl (R)-2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxylate (71.5 g, 193 mmol) in THF/H2O (1:1, 2 L) was added LiOH.H2O (24.2 g, 578 mmol) at 20-25° C. The reaction mixture was stirred at 20-25° C. for 24 hours. The mixture was concentrated, and the aqueous phase was washed with diethyl ether (2 times with 500 mL). The aqueous phase was acidified to pH 2 with 1N HCl (˜400 mL). The precipitated solid was filtered and dried to afford (R)-2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxylic acid (52 g, 78%). MS (ES+) 344.18 (M+H).

後処理

  1. concentrationThe mixture was concentrated
  2. washthe aqueous phase was washed with diethyl ether (2 times with 500 mL)
  3. filtrationThe precipitated solid was filtered
  4. customdried

出典と根拠

ORDレコード
ord-7920f8588bf448158309a362e6ad18eb
出典データセット
uspto-grants-2016_09
特許番号
US09440949B2

関連ノート

読み込み中…