Trifluoroacetic acid → HCID 58452643、化合物

HRID 70673ノート

反応式

HRID 70673 の反応式
FC(F)(F)C(O)=O.[C:8]([C:12]1[CH:17]=[CH:16][C:15](/[C:18](/[C:37]2[N:42]=[C:41]([O:43]C)[C:40]([C:45]#[N:46])=[CH:39][CH:38]=2)=[CH:19]\[C@H:20]2[CH2:24][CH2:23][C:22](=[O:25])[N:21]2CC2C=CC(OC)=CC=2OC)=[CH:14][CH:13]=1)([CH3:11])([CH3:10])[CH3:9]>C1(OC)C=CC=CC=1>[C:8]([C:12]1[CH:13]=[CH:14][C:15](/[C:18](/[C:37]2[NH:42][C:41](=[O:43])[C:40]([C:45]#[N:46])=[CH:39][CH:38]=2)=[CH:19]\[C@H:20]2[CH2:24][CH2:23][C:22](=[O:25])[NH:21]2)=[CH:16][CH:17]=1)([CH3:11])([CH3:9])[CH3:10]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 67398288HCID 67398288、化合物

生成物 1

HCID 58452643HCID 58452643、化合物収率 36.4%

試薬・触媒・溶媒 1

HCID 7519Anisole溶媒

反応条件

温度
85 °C

実験手順

Trifluoroacetic acid (1 mL) was added to a solution of 6-{(E)-1-(4-tert-butylphenyl)-2-[(2R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-2-yl]ethenyl}-2-methoxypyridine-3-carbonitrile (32 mg) in anisole (1 mL), and the mixture was stirred at 85° C. overnight. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→1:5). The resulting compound was dissolved in 1,4-dioxane (1 mL) and 48% hydrobromic acid (1 mL) was added, after which the mixture was stirred at 65° C. for one hour. Saturated aqueous sodium bicarbonate was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:5→chloroform:methanol=5:1) to give the title compound (8 mg, 36%) as a colorless solid.

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→1:5)
  3. dissolutionThe resulting compound was dissolved in 1,4-dioxane (1 mL)
  4. addition48% hydrobromic acid (1 mL) was added
  5. stirringafter which the mixture was stirred at 65° C. for one hour
  6. additionSaturated aqueous sodium bicarbonate was added to the reaction solution
  7. extractionfollowed by extraction with ethyl acetate
  8. washThe organic layer was washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customafter which the solvent was evaporated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:5→chloroform:methanol=5:1)

出典と根拠

ORDレコード
ord-ed7f9f441dea45f29eb37473cb45ca0f
出典データセット
uspto-grants-2014_09
特許番号
US08822503B2

反応ノート

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