Water → Methyl 4-[5-(2-carboxy-2-methylpropyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate

HRID 330201ノート

反応式

HRID 330201 の反応式
FC(F)(F)C(O)=O.[C:8]([C:11]([CH3:40])([CH3:39])[CH:12]([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([CH2:23][CH2:24][CH3:25])[CH:18]=[C:17]2[CH2:26][C:27]1[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][C:28]=1[O:37][CH3:38])O)([OH:10])=[O:9].C([SiH](CC)CC)C.O>C(Cl)(Cl)(Cl)Cl>[C:8]([C:11]([CH3:39])([CH3:40])[CH2:12][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([CH2:23][CH2:24][CH3:25])[CH:18]=[C:17]2[CH2:26][C:27]1[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][C:28]=1[O:37][CH3:38])([OH:10])=[O:9]

参加物

6

反応物 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 19870544Methyl 4-[5-(2-carboxy-1-hydroxy-2-methylpropyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate

生成物 1

HCID 19870564Methyl 4-[5-(2-carboxy-2-methylpropyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate収率 56%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

Trifluoroacetic acid (1.25 g) was added slowly to a stirred solution of methyl 4-[5-(2-carboxy-1 hydroxy-2-methylpropyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate 0.5 g) and triethylsilane (0.128 g) in carbon tetrachloride (7 ml) under an atmosphere of nitrogen. After 35 min, the mixture was poured into water and extracted with ethyl acetate. The combined organic extracts were washed (water (4 times), brine), dried (MgSO4) and evaporated to give a dark oil. The product was purified by flash chromatography, eluting with 90:10:2 toluene:ethyl acetate:acetic acid, to give methyl 4-[5-(2-carboxy-2-methylpropyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate as an oil (0.27 g, 56%): partial NMR (250 MHz, DMSO-d6): 0.82(t, 3H, CH2CH3), 1.02(s, 6H, C(CH3)2), 1.68(m, 2H, CH2CH3), 291(s, 2H, C(CH3)2CH2), 3.82(s, 3H, OCH3), 3.89(s, 3H, OCH3), 4.01(m, 4H, NCH2, ArCH2Ar'), 12.15(br s, about 1H, COOH).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe combined organic extracts were washed (water (4 times), brine)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give a dark oil
  6. customThe product was purified by flash chromatography
  7. washeluting with 90:10:2 toluene

出典と根拠

ORDレコード
ord-92804e4c38764e1886b9b2f5de314b36
出典データセット
uspto-grants-1990_01
特許番号
US04894386

反応ノート

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