4-甲氨基苯甲酸 → UP9V9DB2RD

HRID 967775

反应方程式

HRID 967775 反应方程式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH2:18][CH2:17][C:14]3([CH2:16][O:15]3)[CH2:13][CH2:12]2)=[CH:5][CH:4]=1)#[N:2].[CH3:19][NH:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1.C(=O)([O-])O.[Na+]>FC(F)(F)S([O-])(=O)=O.[Sc+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.C(#N)C.O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH2:18][CH2:17][C:14]([CH2:16][N:20]([CH3:19])[C:21]3[CH:22]=[CH:23][C:24]([C:25]([OH:27])=[O:26])=[CH:28][CH:29]=3)([OH:15])[CH2:13][CH2:12]2)=[CH:5][CH:4]=1)#[N:2]

参与物

7

反应物 3

HCID 663454-甲氨基苯甲酸HCID 516892碳酸氢钠HCID 858197211-[2-(4-Cyanophenyl)ethyl]piperidin-4-spiro-2'-oxirane

产物 1

HCID 12986481UP9V9DB2RD收率 64.5%

试剂、催化剂与溶剂 3

HCID 2734571三氟甲磺酸钪催化剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 6342乙腈溶剂2 次

实验过程

Scandium trifluoromethanesulfonate (609 mg) was added to a mixture of the compound (500 mg) obtained in Step 3 of Example 1, 4-methylaminobenzoic acid (343 mg) and anhydrous acetonitrile (10 mL) under cooling with ice-water, and the mixture was stirred at room temperature for sixty eight hours under nitrogen atmosphere. Water (50 mL) and acetonitrile (10 mL) were added to the resulting mixture and the pH of the mixture was adjusted to above 9 with sodium hydrogen carbonate, insoluble matter was removed by filtration and the filtrate was concentrated under reduced pressure. Water in the residue was removed by azeotrope with ethanol, soluble components in the residue were dissolved in ethanol and the insoluble matter was removed by filtration. The filtrate was concentrated under reduced pressure and then, the residue was dissolved in water (50 mL) and the pH of the solution was adjusted to 7 by diluted hydrochloric acid. Precipitate was collected by filtration and washed with water and ethyl acetate successively under stirring. The precipitate was collected by filtration and dried to obtain the titled compound (524 mg) as powder.

后处理

  1. customwas removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customWater in the residue was removed by azeotrope with ethanol, soluble components in the residue
  4. dissolutionwere dissolved in ethanol
  5. customthe insoluble matter was removed by filtration
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. dissolutionthe residue was dissolved in water (50 mL)
  8. filtrationPrecipitate was collected by filtration
  9. washwashed with water and ethyl acetate successively
  10. stirringunder stirring
  11. filtrationThe precipitate was collected by filtration
  12. customdried

来源与证据

ORD记录
ord-4299d678945a4105be6f8c2c05d2b8d2
来源数据集
uspto-grants-2005_10
专利号
US06956046B2

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