Thiazolidinedione → 5-(4-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl)-propyl}-2-methyl-benzylidene)-thiazolidine-2,4-dione

HRID 502073ノート

反応式

HRID 502073 の反応式
[CH2:1]([C:3]([C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[C:23]([CH3:29])[CH:22]=1)([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]([OH:19])[C:15]([CH3:18])([CH3:17])[CH3:16])=[C:8]([CH3:20])[CH:7]=1)[CH2:4][CH3:5])[CH3:2].[S:30]1[CH2:34][C:33](=[O:35])[NH:32][C:31]1=[O:36].C(O)(=O)C.N1CCCCC1>C1(C)C=CC=CC=1>[CH2:1]([C:3]([C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[C:34]2[S:30][C:31](=[O:36])[NH:32][C:33]2=[O:35])=[C:23]([CH3:29])[CH:22]=1)([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]([OH:19])[C:15]([CH3:17])([CH3:18])[CH3:16])=[C:8]([CH3:20])[CH:7]=1)[CH2:4][CH3:5])[CH3:2]

参加物

5

反応物 3

HCID 5437ThiazolidinedioneHCID 9793820Piperidine, acetateHCID 577634244-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-2-methyl-benzaldehyde

生成物 1

HCID 866047825-(4-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl)-propyl}-2-methyl-benzylidene)-thiazolidine-2,4-dione収率 94%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a mixture of enantiomer 1 of 4-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-2-methyl-benzaldehyde (0.64 g, 1.61 mmol) and toluene (20 mL) is added 90% 2,4-thiazolidinedione (0.25 g, 1.94 mmol), and piperidine acetate (0.04 g, 0.24 mmol). The solution is heated to a reflux overnight and the water removed by a Dean-Stark trap. The solution is diluted with EtOAc (60 mL), washed with water (50 mL), saturated NaHCO3 (50 mL), dried over MgSO4, filtered and concentrated. Purified by ISCO (20%-50% EtOAc gradient) to furnish the title compound (0.75 g, 1.51 mmol, 94%).

後処理

  1. temperatureThe solution is heated to a reflux overnight
  2. customthe water removed by a Dean-Stark trap
  3. additionThe solution is diluted with EtOAc (60 mL)
  4. washwashed with water (50 mL), saturated NaHCO3 (50 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurified by ISCO (20%-50% EtOAc gradient)

出典と根拠

ORDレコード
ord-34888c4144e24cd8988b05ff9eed7f73
出典データセット
uspto-grants-2010_08
特許番号
US07772425B2

反応ノート

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