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p-Toluenesulfonic acid monohydrate → Methyl 2-(4-hydroxy-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate

HRID 10870
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HRID 10870 반응식
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:24])[N:5]([CH2:12][CH:13]([C:18]1([CH3:23])OCC[O:19]1)[C:14]([O:16][CH3:17])=[O:15])[C:6]2=[O:11].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O.O>[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:24])[N:5]([CH2:12][CH:13]([C:18](=[O:19])[CH3:23])[C:14]([O:16][CH3:17])=[O:15])[C:6]2=[O:11]
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참가 물질

4

반응물 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 21982178Methyl 3-(4-hydroxy-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate

생성물 1

HCID 21982266Methyl 2-(4-hydroxy-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate

시약·촉매·용매 1

HCID 18366337Propan-2-one--water (1/1)용매

반응 조건

온도
100 °C

실험 절차

Methyl 3-(4-hydroxy-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.84 g, 2.51 mmol) was dissolved in 24 mL of a solvent mixture of acetone/water (v/v=5/1), and p-toluenesulfonic acid monohydrate (about 0.19 g) was then added to the obtained solution. The resulting mixture was refluxed at 100° C. for 2 days. After the reaction was completed, the reaction mixture was concentrated under a reduced pressure and then extracted with dichloromethane. The desired product was obtained (0.55 mg, 75%) by performing column chromatography (eluent: n-hexane/ethyl acetate=2/1).

후처리

  1. additionwas then added to the obtained solution
  2. concentrationthe reaction mixture was concentrated under a reduced pressure
  3. extractionextracted with dichloromethane

출처 및 근거

ORD 기록
ord-f68dd14708ea4825b48a089d06cc2308
출처 데이터셋
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07094908B2

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