1,4-Dioxane → 3-{(2R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxyethylamino]propyl}-1H-indole-7-carboxylic acid

HRID 1351937ノート

反応式

HRID 1351937 の反応式
C(N(CC)[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[NH:13][CH:12]=[C:11]2[CH2:15][C@H:16]([NH:18][CH2:19][C@@H:20]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=1)[OH:21])[CH3:17])=[O:5])C.[O:31]1CCOCC1>Cl>[Cl:28][C:24]1[CH:23]=[C:22]([C@@H:20]([OH:21])[CH2:19][NH:18][C@H:16]([CH3:17])[CH2:15][C:11]2[C:10]3[C:14](=[C:6]([C:4]([OH:31])=[O:5])[CH:7]=[CH:8][CH:9]=3)[NH:13][CH:12]=2)[CH:27]=[CH:26][CH:25]=1

参加物

4

反応物 2

HCID 312751,4-DioxaneHCID 694562293-{(2 R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxyethyl-amino]propyl}-1H-indole-7-carboxylic acid diethylamide

生成物 1

HCID 694577363-{(2R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxyethylamino]propyl}-1H-indole-7-carboxylic acid収率 30%

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

反応条件

温度
150 °C

実験手順

A solution of 3-{(2 R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxyethyl-amino]propyl}-1H-indole-7-carboxylic acid diethylamide (175 mg, 0.41 mmol) in 1,4-dioxane (7 mL) and 6N hydrochloric acid (7 mL) is stirred with heating at 150° C. for 7 hours in a closed system. After cooling, the mixture is evaporated under reduced pressure to remove dioxane, and the resultant is neutralized with an aqueous Na2CO3 solution. The precipitates are filtered, and purified by reversed phase column (octa-decylsilyl, methanol/water=1/1→3/1) to give the desired 3-{(2R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxyethylamino]propyl}-1H-indole-7-carboxylic acid (45 mg, yield: 30%).

後処理

  1. temperatureAfter cooling
  2. customthe mixture is evaporated under reduced pressure
  3. customto remove dioxane
  4. filtrationThe precipitates are filtered
  5. custompurified by reversed phase column (octa-decylsilyl, methanol/water=1/1→3/1)

出典と根拠

ORDレコード
ord-46ccc422023c4242b73ea0d0a0dbc462
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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