Citric Acid → 4-[(1S)-1-({[1-(biphenyl-4-ylmethyl)-1H-indol-7-yl]carbonyl}amino)ethyl]benzoic acid

HRID 1909908ノート

反応式

HRID 1909908 の反応式
[C:1]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[C:17]([NH:19][C@H:20]([C:22]3[CH:31]=[CH:30][C:25]([C:26]([O:28]C)=[O:27])=[CH:24][CH:23]=3)[CH3:21])=[O:18])[CH:10]=[CH:9]2)=[CH:3][CH:2]=1.CO.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[C:1]1([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:2]=[CH:3][C:4]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[C:17]([NH:19][C@H:20]([C:22]3[CH:23]=[CH:24][C:25]([C:26]([OH:28])=[O:27])=[CH:30][CH:31]=3)[CH3:21])=[O:18])[CH:10]=[CH:9]2)=[CH:5][CH:6]=1

参加物

6

反応物 4

HCID 311Citric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 58306872methyl 4-[(1S)-1-({[1-(biphenyl-4-ylmethyl)-1H-indol-7-yl]carbonyl}amino)ethyl]benzoate

生成物 1

HCID 583066634-[(1S)-1-({[1-(biphenyl-4-ylmethyl)-1H-indol-7-yl]carbonyl}amino)ethyl]benzoic acid収率 85.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
65 °C

実験手順

To methyl 4-[(1S)-1-({[1-(biphenyl-4-ylmethyl)-1H-indol-7-yl]carbonyl}amino)ethyl]benzoate (0.30 g) were added methanol (4.0 mL), THF (4.0 mL), and a 1 M aqueous sodium hydroxide solution (3.0 mL), followed by stirring at 65° C. for 2 hours and then at room temperature for 3 days. To the reaction mixture was added a 10% aqueous citric acid solution (4.0 mL), and the precipitated solid was collected by filtration, washed with water and a mixture of diethyl ether/hexane (1/1), and dried at 60° C. under reduced pressure to obtain 4-[(1S)-1-({[1-(biphenyl-4-ylmethyl)-1H-indol-7-yl]carbonyl}amino)ethyl]benzoic acid (0.25 g).

後処理

  1. waitat room temperature for 3 days
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with water
  4. additiona mixture of diethyl ether/hexane (1/1)
  5. customdried at 60° C. under reduced pressure

出典と根拠

ORDレコード
ord-f2214388ebd64b279ed511f6bc3b5401
出典データセット
uspto-grants-2013_12
特許番号
US08598355B2

反応ノート

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