Dimethylformamide → 1-(1-Ethylpropyl)-6-methylergoline-8carboxylic acid

HRID 570041ノート

反応式

HRID 570041 の反応式
[CH3:1][N:2]1[CH:7]2[CH2:8][C:9]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][C:16]=4[CH:6]2[CH2:5][CH:4]([C:18]([OH:20])=[O:19])[CH2:3]1)[NH:11][CH:10]=3.[OH-].[K+].CN(C=O)C.[C:28]1(C)[CH:33]=[CH:32]C(S(OC(CC)CC)(=O)=O)=[CH:30][CH:29]=1>O>[CH2:29]([CH:28]([N:11]1[C:12]2[C:17]3[C:9]([CH2:8][C@@H:7]4[C@@H:6]([C:16]=3[CH:15]=[CH:14][CH:13]=2)[CH2:5][CH:4]([C:18]([OH:20])=[O:19])[CH2:3][N:2]4[CH3:1])=[CH:10]1)[CH2:33][CH3:32])[CH3:30]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 14797Potassium HydroxideHCID 622987NoName_3979HCID 12568537Pentan-3-yl 4-methylbenzene-1-sulfonate

生成物 1

HCID 138780051-(1-Ethylpropyl)-6-methylergoline-8carboxylic acid収率 59.8%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A 250 ml, three-neck round bottom flask was charged with 10.0 g (33.9 mmol) of 92% pure 9,10-dihydrolysergic acid, 10.3 g (158 mmol) of 86% pure powdered potassium hydroxide and 75 ml of DMF. The mixture was stirred until the solid constituents were completely dissolved, and 17.9 g (73.9 mmol) of p-toluenesulfonic acid, 1-ethylpropyl ester was added. The reaction mixture was stirred at room temperature overnight and 300 ml of deionized water was added. The mixture was filtered, and 1N hydrochloric acid was added to the filtrate until the pH was adjusted to approximately 6.5. The precipitated solid was collected by vacuum filtration and rinsed with water to provide 6.9 g of 1-(1-ethylpropyl)-6-methylergoline-8-carboxylic acid. The identity of the solid was determined by thin layer chromatography employing chloroform:methanol:acetic acid (18:6:1, v:v:v) as the solvent system as compared to an authentic reference standard. The products obtained from Example 1 and Example 2 were combined to provide 7.6 g of solid, which was recrystallized from methanol to provide 2.1 g of the desired product following drying of the solid in vacuo. The purity of the product was 95.6% as determined by HPLC as compared to an authentic reference standard.

後処理

  1. dissolutionwere completely dissolved
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. filtrationThe mixture was filtered
  4. addition1N hydrochloric acid was added to the filtrate until the pH
  5. filtrationThe precipitated solid was collected by vacuum filtration
  6. washrinsed with water

出典と根拠

ORDレコード
ord-08baa4e6f04a4306b7dbd408f775296b
出典データセット
uspto-grants-1988_03
特許番号
US04734501

反応ノート

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