7-Methyl-8-oxononanoic acid → 6-(4,5,6-triiodo-2,3-dimethyl-3H-3-indolyl)hexanoic acid

HRID 508295ノート

反応式

HRID 508295 の反応式
[I:1][C:2]1[CH:3]=[C:4]([NH:10]N)[CH:5]=[C:6]([I:9])[C:7]=1[I:8].[CH3:12][CH:13]([C:22](=O)[CH3:23])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20]>C(O)(=O)C>[I:1][C:2]1[C:7]([I:8])=[C:6]([I:9])[CH:5]=[C:4]2[C:3]=1[C:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])([CH3:12])[C:22]([CH3:23])=[N:10]2

参加物

4

反応物 2

HCID 222668237-Methyl-8-oxononanoic acidHCID 866953333,4,5-Triiodophenylhydrazine

生成物 1

HCID 717361666-(4,5,6-triiodo-2,3-dimethyl-3H-3-indolyl)hexanoic acid収率 23.5%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A mixture of 3,4,5-triiodophenylhydrazine 2 g (4 mmol) and 1 g (5 mmol) of 7-methyl-8-oxononanoic acid was refluxed in 15 mL of acetic acid for 16 hours. The acetic acid was evaporated, and the residue was dissolved in CHCl3, and washed by aqueous NaHCO3 and water. The organic layer was dried with CaCl2 and solvent was removed under reduced pressure by a rotary evaporator. The residue was column purified (Silica gel 60, 0-4% methanol-chloroform) to give 0.6 g of 6-(4,5,6-triiodo-2,3-dimethyl-3H-3-indolyl)hexanoic acid. 1H-NMR (200 MHz, DMSO-d6), δ, ppm: 8.02 (1H, s, arom.), 2.16 (3H, s, 2-CH3), 2.07 (2H, t, CH2COOH), 1.65-1.05 (6H, m, CH2), 1.26 (3H, s, CH3), 0.58-0.20 (2H, m, CH2).

後処理

  1. customThe acetic acid was evaporated
  2. dissolutionthe residue was dissolved in CHCl3
  3. washwashed by aqueous NaHCO3 and water
  4. dry with materialThe organic layer was dried with CaCl2 and solvent
  5. customwas removed under reduced pressure by a rotary evaporator
  6. custompurified (Silica gel 60, 0-4% methanol-chloroform)

出典と根拠

ORDレコード
ord-0c955a06e7554394be971b58ac2fbb7f
出典データセット
uspto-grants-2015_08
特許番号
US09095612B2

反応ノート

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