Lithium Hydroxide → 3-Cyclopentyl-2-(4-pyridin-3-yl-phenyl)-propionic acid

HRID 1935206ノート

反応式

HRID 1935206 の反応式
C[O:2][C:3](=[O:23])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Li+]>O1CCCC1>[CH:6]1([CH2:5][CH:4]([C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:15][CH:16]=2)[C:3]([OH:23])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 674834933-Cyclopentyl-2-(4-pyridin-3-yl-phenyl)-propionic acid methyl ester

生成物 1

HCID 224679003-Cyclopentyl-2-(4-pyridin-3-yl-phenyl)-propionic acid収率 63.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

A solution of 3-cyclopentyl-2-(4-pyridin-3-yl-phenyl)-propionic acid methyl ester (450 mg, 1.45 mmol) in tetrahydrofuran (5 mL) was treated with a 0.8M aqueous lithium hydroxide solution (2.18 mL, 1.74 mmol). The resulting reaction mixture was stirred at 25° C. for 3 d. The reaction mixture was then partitioned between water (50 mL) and ethyl acetate (50 mL), and the layers were separated. The aqueous layer was further extracted with ethyl acetate (2×50 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting solid was purified by precipitation from methylene chloride/ethyl acetate to afford 3-cyclopentyl-2-(4-pyridin-3-yl-phenyl)-propionic acid (271 mg, 63%) as a white solid: mp 136-138° C.; EI-HRMS m/e calcd for C19H21NO2 (M+) 295.1572, found 295.1572.

後処理

  1. customThe resulting reaction mixture
  2. customThe reaction mixture was then partitioned between water (50 mL) and ethyl acetate (50 mL)
  3. customthe layers were separated
  4. extractionThe aqueous layer was further extracted with ethyl acetate (2×50 mL)
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting solid was purified by precipitation from methylene chloride/ethyl acetate

出典と根拠

ORDレコード
ord-eb328bd7fcde41d288e7dbf20e7dff55
出典データセット
uspto-grants-2002_05
特許番号
US06384220B2

反応ノート

読み込み中…