Hydrochloric Acid → HCID 178490506、化合物

HRID 2225520

反応式

HRID 2225520 の反応式
P(Cl)(OCC)(OCC)=O.C([O:13][C:14]1[CH:24]=[CH:23][C:17]([CH:18]=[CH:19][C:20]([OH:22])=O)=[CH:16][C:15]=1[O:25][CH3:26])(=O)C.[CH3:27][N:28]([CH3:41])[CH2:29][CH2:30][CH2:31][CH2:32][NH:33][C@H:34]1[CH2:39][CH2:38][C@H:37]([CH3:40])[CH2:36][CH2:35]1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C1C=CN=CC=1.CO.C(Cl)Cl.C(N(CC)CC)C>[CH3:41][N:28]([CH3:27])[CH2:29][CH2:30][CH2:31][CH2:32][N:33]([C@H:34]1[CH2:39][CH2:38][C@H:37]([CH3:40])[CH2:36][CH2:35]1)[C:20](=[O:22])[CH:19]=[CH:18][C:17]1[CH:23]=[CH:24][C:14]([OH:13])=[C:15]([O:25][CH3:26])[CH:16]=1

参加物

10

反応物 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 13139Diethyl chlorophosphateHCID 757754-Acetoxy-3-methoxy-cinnamic acidHCID 178483465HCID 178483465、化合物

生成物 1

HCID 178490506HCID 178490506、化合物

試薬・触媒・溶媒 4

HCID 142844-(Dimethylamino)pyridine触媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

A mixture solution of 2.8 ml of diethyl chlorophosphate, 2.7 ml of triethylamine, 2.3 g of 4-acetoxy-3-methoxycinnamic acid, and 100 ml of methylene chloride was stirred for 1 hour at room temperature. Next, 3.5 ml of N-(4-dimethylaminobutyl)-trans-4-methylcyclohexylamine (Example 74) and 0.5 g of 4-dimethylaminopyridine were added to the solution under ice-cooling. The solution was stirred further for 4 hours at room temperature. Then, 100 ml of methanol and 5 g of potassium carbonate were added to the solution, and the solution was stirred for 1.5 hours at room temperature. After stirring, the reaction solution was neutralized with 2N hydrochloric acid under ice-cooling. The solution was extracted three times with 50 ml of ethyl acetate. The organic layer obtained was washed twice with an aqueous sodium hydrogencarbonate solution and twice with aqueous sodium chloride solution, and was dried over magnesium sulfate. Thereafter, the solvent was removed in vacuo. The product obtained was recrystallized from methylene chloride/either, yielding 1.7 g of N-(4-dimethylaminobutyl)-N-(trans-4-methylcyclohexyl)-4-hydroxy-3-methoxycinnamamide (a compound of the present this invention) as a pale yellow oily oil, which had the following physiochemical properties:

後処理

  1. temperaturecooling
  2. stirringthe solution was stirred for 1.5 hours at room temperature
  3. stirringAfter stirring
  4. temperaturecooling
  5. extractionThe solution was extracted three times with 50 ml of ethyl acetate
  6. customThe organic layer obtained
  7. washwas washed twice with an aqueous sodium hydrogencarbonate solution and twice with aqueous sodium chloride solution
  8. dry with materialwas dried over magnesium sulfate
  9. customThereafter, the solvent was removed in vacuo
  10. customThe product obtained
  11. customwas recrystallized from methylene chloride/either

出典と根拠

ORDレコード
ord-c79e22688b6a49a1bcef35cccfc4002f
出典データセット
uspto-grants-1994_09
特許番号
US05344845

関連ノート

読み込み中…