Lithium Hydroxide → (S)-3-cyclohexyl-2-(2-oxo-4-m-tolyloxy-2,5-dihydro-pyrrol-1-yl)-propionic acid

HRID 19282ノート

反応式

HRID 19282 の反応式
C[O:2][C:3](=[O:26])[C@@H:4]([N:12]1[CH2:16][C:15]([O:17][C:18]2[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=2)=[CH:14][C:13]1=[O:25])[CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Li+]>O1CCCC1.O>[CH:6]1([CH2:5][C@H:4]([N:12]2[CH2:16][C:15]([O:17][C:18]3[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=3)=[CH:14][C:13]2=[O:25])[C:3]([OH:26])=[O:2])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 66894935(S)-3-cyclohexyl-2-(2-oxo-4-m-tolyloxy-2,5-dihydro-pyrrol-1-yl)-propionic acid methyl ester

生成物 1

HCID 66894940(S)-3-cyclohexyl-2-(2-oxo-4-m-tolyloxy-2,5-dihydro-pyrrol-1-yl)-propionic acid収率 79%

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

反応条件

温度
23 °C

実験手順

To a stirred solution of (S)-3-cyclohexyl-2-(2-oxo-4-m-tolyloxy-2,5-dihydro-pyrrol-1-yl)-propionic acid methyl ester (0.570 g, 0.002 mol) in tetrahydrofuran-water (3:1, 10 mL) was added lithium hydroxide (0.201 g, 0.008 mol). The reaction mixture was stirred at 23° C. for 2 h. After this time, the mixture was concentrated and the reaction mixture was diluted with water. The reaction mixture was acidified with 2N hydrochloric acid, during which time precipitation occurred. The precipitate was removed by filtration, washed with cold water and dried in vacuo to obtain (S)-3-cyclohexyl-2-(2-oxo-4-m-tolyloxy-2,5-dihydro-pyrrol-1-yl)-propionic acid (430 mg, 79%) as a light brown solid.

後処理

  1. concentrationAfter this time, the mixture was concentrated
  2. additionthe reaction mixture was diluted with water
  3. customThe reaction mixture was acidified with 2N hydrochloric acid, during which time precipitation
  4. customThe precipitate was removed by filtration
  5. washwashed with cold water
  6. customdried in vacuo

出典と根拠

ORDレコード
ord-14531b1bfb6843b299ffdd28eb8e0016
出典データセット
uspto-grants-2010_06
特許番号
US07741327B2

反応ノート

読み込み中…