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Phthalic anhydride, 3-acetoxy- → 1,3-Dioxo-2-(2,6-dioxopiperidin-3-yl)-4-acetoxyisoindoline

HRID 533360
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HRID 533360 반응식
[C:1]([O:4][C:5]1[CH:15]=[CH:14][CH:13]=[C:7]2[C:8]([O:10][C:11](=[O:12])[C:6]=12)=O)(=[O:3])[CH3:2].FC(F)(F)C(O)=O.[NH2:23][CH:24]1[CH2:30][CH2:29][C:28](=[O:31])[NH:27][C:25]1=[O:26].CC([O-])=O.[Na+]>C(O)(=O)C>[O:10]=[C:8]1[C:7]2[C:6](=[C:5]([O:4][C:1](=[O:3])[CH3:2])[CH:15]=[CH:14][CH:13]=2)[C:11](=[O:12])[N:23]1[CH:24]1[CH2:30][CH2:29][C:28](=[O:31])[NH:27][C:25]1=[O:26]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 294175Phthalic anhydride, 3-acetoxy-HCID 517045Sodium AcetateHCID 53447112Trifluoroacetic acid--3-aminopiperidine-2,6-dione (1/1)

생성물 1

HCID 250152191,3-Dioxo-2-(2,6-dioxopiperidin-3-yl)-4-acetoxyisoindoline수율 66%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

1,3-Dioxo-2-(2,6-dioxopiperidin-3-yl)-4-acetoxyisoindoline was prepared and isolated as follows. A mixture of 3-acetoxyphthalic anhydride (40 mg), aminoglutarimide trifluoroacetate (47 mg), and NaOAc (32 mg) in acetic acid (2 mL) was refluxed for 5 h. The solvent was evaporated, water (10 mL) was added, and the resulting solution was stirred for several minutes. The solid was filtered out and recrystallized from ethyl acetate to give 1,3-dioxo-2-(2,6-dioxopiperidin-3-yl)-4-acetoxyisoindoline as pale yellow crystals (35 mg, 66%): 1H NMR (DMSO) δ 11.16 (s, 1H), 11.07 (s, 1H), 7.64 (t, J=7.2 Hz, 1H), 7.22-7.31 (m, 2H), 5.05 (dd, J=5.4 Hz, J=12.5 Hz, 1H), 2.87-2.92 (m, 2H), 2.48 (s, 3H), 2.08-2.00 (m, 2H).

후처리

  1. custom1,3-Dioxo-2-(2,6-dioxopiperidin-3-yl)-4-acetoxyisoindoline was prepared
  2. customisolated
  3. temperaturewas refluxed for 5 h
  4. customThe solvent was evaporated
  5. additionwater (10 mL) was added
  6. filtrationThe solid was filtered out
  7. customrecrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-dc2da9662d7d4c2984161ee8c08bd700
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08853253B2

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