Hydrochloric Acid → 1,3-Dioxo-2-(2,6-dioxo-3-fluoropiperidin-3-yl)isoindoline

HRID 618695노트

반응식

HRID 618695 반응식
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]1[CH2:17][CH2:16][C:15](=[O:18])[N:14](C(OC(C)(C)C)=O)[C:13]1=[O:26].[H-].[Na+].Cl([F:33])(=O)(=O)=O.Cl>CN(C)C=O.C(Cl)Cl>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1([F:33])[CH2:17][CH2:16][C:15](=[O:18])[NH:14][C:13]1=[O:26]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 15408802Tert-butyl 3-(1,3-dioxoisoindolin-2-yl)-2,6-dioxopiperidine-1-carboxylate

생성물 1

HCID 98820501,3-Dioxo-2-(2,6-dioxo-3-fluoropiperidin-3-yl)isoindoline

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 1,3-dioxo-2-(1-tert.-butoxycarbonyl-2,6-dioxopiperidin-3-yl)-isoindoline (1.0 g. 2.8 mmol) in dimethylformamide (10 mL) is added sodium hydride (112 mg, 2.8 mmol, 60%) at room temperature. After about 30 minutes, perchloryl fluoride (5 mmol) is bubbled into the mixture. The mixture is stirred with methylene chloride (10 mL) and 1N hydrochloric acid (10 mL) for one hour. The organic layer is separated and the solvent removed in vacuo to yield 1,3-dioxo-2-(2,6-dioxo-3-fluoropiperidin-3-yl)isoindoline which can be further purified through chromatography.

후처리

  1. customThe organic layer is separated
  2. customthe solvent removed in vacuo

출처 및 근거

ORD 기록
ord-f5926b8a5c4e446db6559f160e6d14f7
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05955476

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