Potassium Hydroxide → N-(5-carboxypentyl)-3-(1-naphthoyl)-1H-indole

HRID 55923

反応式

HRID 55923 の反応式
C([O:3][C:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([C:20]([C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][CH:23]=2)=[O:21])=[CH:12]1)=[O:5])C.[OH-].[K+]>C1COCC1.O>[C:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([C:20]([C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][CH:23]=2)=[O:21])=[CH:12]1)([OH:5])=[O:3]

参加物

4

反応物 2

HCID 14797Potassium HydroxideHCID 68159362N-(5-Ethoxycarbonylpentyl)-3-(1-naphthoyl)-1H-indole

生成物 1

HCID 68159208N-(5-carboxypentyl)-3-(1-naphthoyl)-1H-indole

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

反応条件

温度
60 °C

実験手順

To a solution of 2 (5.0 g, 12 mmol) in a mixture of THF/H2O (1:1) was added potassium hydroxide (1.7 g) and the mixture was stirred at 60° C. for 1 h. The THF was removed under vacuum, the aqueous solution acidified to pH 1 by the addition of hydrochloric acid solution (1N) and extracted by ethyl acetate (3×100 ml). The combined organic phases were washed by water (100 ml), brine solution (100 ml), dried over sodium sulphate, filtered and concentrated to dryness. The crude product obtained was dissolved in ethyl acetate (10 ml) and the Hapten-A precipitated by the addition of a mixture of ether/hexane as a white solid, filtered and dried under high vacuum to give Hapten-A (3.6 g, 78%).

後処理

  1. customThe THF was removed under vacuum
  2. additionthe aqueous solution acidified to pH 1 by the addition of hydrochloric acid solution (1N)
  3. extractionextracted by ethyl acetate (3×100 ml)
  4. washThe combined organic phases were washed by water (100 ml), brine solution (100 ml)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-17e8838374e3476c959697b133c82e3a
出典データセット
uspto-grants-2016_09
特許番号
US09434687B2

関連ノート

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