Potassium Hydroxide → (3-{(2R)-2-[(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethylamino]propyl}-1H-indol-7-yloxy)acetic acid

HRID 1351927ノート

反応式

HRID 1351927 の反応式
C(N(CC)[C:4](=[O:30])[CH2:5][O:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:15]=1[NH:14][CH:13]=[C:12]2[CH2:16][C@H:17]([NH:19][CH2:20][C@H:21]([OH:29])[C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)[CH3:18])C.[OH-:33].[K+]>O.C(O)C>[OH:29][C@H:21]([C:22]1[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=1)[CH2:20][NH:19][C@H:17]([CH3:18])[CH2:16][C:12]1[C:11]2[C:15](=[C:7]([O:6][CH2:5][C:4]([OH:33])=[O:30])[CH:8]=[CH:9][CH:10]=2)[NH:14][CH:13]=1

参加物

5

反応物 2

HCID 14797Potassium HydroxideHCID 69458605N,N-diethyl-2-(3-{(2R)-2-[(2 R)-2-hydroxy-2-(4-hydroxyphenyl) ethylamino]propyl}-1H-indol-7-yl-oxy)acetamide

生成物 1

HCID 21098824(3-{(2R)-2-[(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethylamino]propyl}-1H-indol-7-yloxy)acetic acid収率 68%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒2 回

実験手順

A solution of N,N-diethyl-2-(3-{(2R)-2-[(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethylamino]propyl}-1H-indol-7-yloxy) acetamide (12 mg, 0.027 mmol) and potassium hydroxide (60 mg, 1.1 mmol) in water (0.5 mL) and ethanol (0.5 mL) is stirred at 60° C. for 6 hours. After cooling, the mixture is concentrated and acidified by addition of water (30 mL) and acetic acid. The resultant is purified by reversed phase column chromatography (COSMOSIL 75C18-OPN (Nacalai Tesque) (octadecyl-silica gel, particle diameter: 75 μm, hereinafter, the same), water→water/methanol=10/ 1) to give the desired (3-{(2R)-2-[(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethylamino]propyl}-1H-indol-7-yloxy)acetic acid (7 mg, yield: 68%).

後処理

  1. temperatureAfter cooling
  2. concentrationthe mixture is concentrated
  3. additionacidified by addition of water (30 mL) and acetic acid
  4. customThe resultant is purified by reversed phase column chromatography (COSMOSIL 75C18-OPN (Nacalai Tesque) (octadecyl-silica gel, particle diameter

出典と根拠

ORDレコード
ord-c4943b9bf95b4bfa8e34482279f12e85
出典データセット
uspto-grants-2007_05
特許番号
US07217724B2

反応ノート

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