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

HRID 19001노트

반응식

HRID 19001 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
103 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-910398ec618d4efe85335c6f11fd5fa4
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741327B2

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