Water → 2-[1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl-methyl)-1H-pyrazol-3-yl]-isoindole-1,3-dione

HRID 19001ノート

反応式

HRID 19001 の反応式
[NH:1]1[CH:5]=[CH:4][C:3]([N:6]2[C:14](=[O:15])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]2=[O:16])=[N:2]1.[CH3:17][C:18]1([CH3:35])[O:22][C@H:21]([CH2:23]OS(C2C=CC(Cl)=CC=2)(=O)=O)[CH2:20][O:19]1.CC(C)([O-])C.[Na+].O>O1CCOCC1>[CH3:17][C:18]1([CH3:35])[O:22][C@H:21]([CH2:23][N:1]2[CH:5]=[CH:4][C:3]([N:6]3[C:14](=[O:15])[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[C:7]3=[O:16])=[N:2]2)[CH2:20][O:19]1

参加物

6

反応物 4

HCID 962WaterHCID 23676156Sodium t-butoxideHCID 866352284-chloro-benzenesulfonic acid (S)-2,2-dimethyl-[1,3]dioxolan-4-yl-methyl esterHCID 178514958HCID 178514958、化合物

生成物 1

HCID 593449502-[1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl-methyl)-1H-pyrazol-3-yl]-isoindole-1,3-dione収率 74.1%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
103 °C

実験手順

A mixture of 2-(1H-pyrazol-3-yl)-isoindole-1,3-dione (5.00 g, 23.5 mmol), 4-chloro-benzenesulfonic acid (S)-2,2-dimethyl-[1,3]dioxolan-4-yl-methyl ester (8.00 g, 26.1 mmol), and sodium t-butoxide (2.78 g, 28.9 mmol) in 1,4-dioxane (50 mL) was refluxed (103° C.) for 24 h. Upon cooling to 25° C., water (55 mL) was added. The mixture became cloudy and crystallization was observed. Then, water (50 mL) was slowly added over 30 min. Subsequent filtration, washing with water, and suction drying provided 2-[1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl-methyl)-1H-pyrazol-3-yl]-isoindole-1,3-dione (5.69 g, 74.1%) as an off-white solid: LR-ES-MS m/z calculated for C17H17N3O4 [M]+ 327, observed [M+H]+ 328.

後処理

  1. temperatureUpon cooling to 25° C.
  2. customcrystallization
  3. additionThen, water (50 mL) was slowly added over 30 min
  4. filtrationSubsequent filtration
  5. washwashing with water, and suction
  6. customdrying

出典と根拠

ORDレコード
ord-910398ec618d4efe85335c6f11fd5fa4
出典データセット
uspto-grants-2010_06
特許番号
US07741327B2

反応ノート

読み込み中…