Hydrochloric Acid → 4-[3-[3-[Bis(4-isobutylphenyl)methoxy]benzoyl]indol-1-yl]butyric acid

HRID 249168ノート

反応式

HRID 249168 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[C:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH:8]=1)=[O:6].[H-].[Na+].[CH2:27]([C:31]1[CH:36]=[CH:35][C:34]([CH:37]([C:39]2[CH:44]=[CH:43][C:42]([CH2:45][CH:46]([CH3:48])[CH3:47])=[CH:41][CH:40]=2)Br)=[CH:33][CH:32]=1)[CH:28]([CH3:30])[CH3:29].Cl>CN(C)C=O.O1CCCC1.C(OCC)(=O)C>[CH2:45]([C:42]1[CH:43]=[CH:44][C:39]([CH:37]([C:34]2[CH:35]=[CH:36][C:31]([CH2:27][CH:28]([CH3:30])[CH3:29])=[CH:32][CH:33]=2)[O:1][C:2]2[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=2)[C:5]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH:8]=2)=[O:6])=[CH:40][CH:41]=1)[CH:46]([CH3:48])[CH3:47]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 190247084-[3-(3-Hydroxybenzoyl)indol-1-yl]butyric acidHCID 19101766HCID 19101766、化合物

生成物 1

HCID 190247724-[3-[3-[Bis(4-isobutylphenyl)methoxy]benzoyl]indol-1-yl]butyric acid収率 12.9%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
25 °C

実験手順

A solution of 4-[3-(3-hydroxybenzoyl)indol-1-yl]butyric acid (500 mg) in N,N-dimethylformamide (5 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 136 mg) in N,N-dimethylformamide (10 ml) at 25° . The mixture was stirred at 25° C. for 1 hour, and a solution of bis (4-isobutylphenyl)bromomethane (1.11 g) in tetrahydrofuran (10 ml) was added at 0° C. After stirred at 25° C. overnight, the mixture was poured into a mixture of ethyl acetate and 1N hydrochloric acid. The organic layer was separated, washed with water and brine, and dried over magnesium sulfate. After evaporation of the solvent, the residue was chromatographed on silica gel (20 g) eluting with 2% methanol in chloroform to give 4-[3-[3-[bis(4-isobutylphenyl)methoxy]benzoyl]indol-1-yl]butyric acid (120 mg) as colorless crystals.

後処理

  1. stirringAfter stirred at 25° C. overnight
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of the solvent
  6. customthe residue was chromatographed on silica gel (20 g)
  7. washeluting with 2% methanol in chloroform

出典と根拠

ORDレコード
ord-1f22e7be4adb48989a6f57358ff78c52
出典データセット
uspto-grants-1993_05
特許番号
US05212320

反応ノート

読み込み中…