ubiquitin cross-reactive protein → 5-氰基-2-糠醛

HRID 1952849

反应方程式

HRID 1952849 反应方程式
C([Li])CCC.C(NC(C)C)(C)C.[C:13]([C:15]1[O:16][CH:17]=[CH:18][CH:19]=1)#[N:14].C(O)(=O)C[C:22](CC(O)=O)(C(O)=O)[OH:23]>CCCCCC.O1CCCC1.O.CN(C)C=O>[C:13]([C:15]1[O:16][C:17]([CH:22]=[O:23])=[CH:18][CH:19]=1)#[N:14]

参与物

9

反应物 4

HCID 311ubiquitin cross-reactive proteinHCID 7912二异丙胺HCID 692452-氰基呋喃HCID 178418339正丁基锂

产物 1

HCID 6421395-氰基-2-糠醛收率 42.3%

试剂、催化剂与溶剂 4

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 6228N,N-二甲基甲酰胺溶剂HCID 8028四氢呋喃溶剂2 次HCID 8058正己烷溶剂

反应条件

温度
-78 °C

实验过程

165 ml (264 mmol) of a 1.6 molar solution of n-butyllithium in n-hexane were added over the course of 20 min to a solution of 26.7 g (264 mmol) of diisopropylamine in 600 ml of tetrahydrofuran cooled to -78° C. The solution was allowed to reach -20° C., again cooled to -75° C. and, at this temperature, a solution of 22.3 g (240 mmol) of 2-cyanofuran in 100 ml of tetrahydrofuran were slowly added dropwise. After stirring for 30 min, 93 ml of dimethylformamide were slowly added dropwise, and the mixture was stirred for a further 30 min. For workup, a solution of 40 g of citric acid in 200 ml of water was added at -70° C. After concentration in a rotary evaporator, 600 ml of saturated sodium chloride solution were added, and the mixture was extracted three times with 200 ml of diethyl ether each time. The combined organic extracts were dried over magnesium sulfate. The desiccant was filtered off and then the solvent was distilled off under water pump vacuum and the residue was purified by column chromatography (mobile phase dichloromethane). The eluate was concentrated and the residue was subjected to steam distillation (boiling range of the azeotrope with water: 60-65° C. at p=0.1 mm Hg). Extraction of the distillate with diethyl ether, drying of the organic phase and concentration of the solution resulted in 10.6 g (88 mmol, 36%) of the title compound. 1H-NMR (270 MHz, d6 -DMSO): δ=7.7 (d, 1H), 7.8 (d, 1H), 9.75 (s, 1H).

后处理

  1. customto reach -20° C.
  2. temperatureagain cooled to -75° C. and, at this temperature
  3. stirringthe mixture was stirred for a further 30 min
  4. concentrationAfter concentration
  5. customin a rotary evaporator, 600 ml of saturated sodium chloride solution
  6. additionwere added
  7. extractionthe mixture was extracted three times with 200 ml of diethyl ether each time
  8. dry with materialThe combined organic extracts were dried over magnesium sulfate
  9. filtrationThe desiccant was filtered off
  10. distillationthe solvent was distilled off under water pump vacuum
  11. customthe residue was purified by column chromatography (mobile phase dichloromethane)
  12. concentrationThe eluate was concentrated
  13. distillationthe residue was subjected to steam distillation (
  14. custom60-65° C.
  15. extractionExtraction of the distillate with diethyl ether
  16. customdrying of the organic phase and concentration of the solution

来源与证据

ORD记录
ord-1b30c6549bf14b67b22d83300eb8b84a
来源数据集
uspto-grants-2000_09
专利号
US06114358

关联笔记

加载中…