Ammonium Chloride → 1,3-Dioxo-2-(1-tert-butoxycarbonyl-2,6-dioxo-3-fluoropiperidin-3-yl)isoindoline

HRID 618693노트

반응식

HRID 618693 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[O:11]=[C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](=[O:21])[N:13]1[CH:22]1[CH2:27][CH2:26][C:25](=[O:28])[N:24]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:23]1=[O:36].C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:47])(=O)=O)=CC=1.[Cl-].[NH4+]>O1CCCC1.O.C(OCC)(=O)C>[O:21]=[C:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12](=[O:11])[N:13]1[C:22]1([F:47])[CH2:27][CH2:26][C:25](=[O:28])[N:24]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[C:23]1=[O:36]

참가 물질

8

반응물 4

HCID 25517Ammonium ChlorideHCID 588007N-FluorobenzenesulfonimideHCID 2733832Lithium HexamethyldisilazideHCID 15408802Tert-butyl 3-(1,3-dioxoisoindolin-2-yl)-2,6-dioxopiperidine-1-carboxylate

생성물 1

HCID 154280601,3-Dioxo-2-(1-tert-butoxycarbonyl-2,6-dioxo-3-fluoropiperidin-3-yl)isoindoline

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

In a similar fashion, lithium bis(trimethylsilyl)amide (24 mL, 24 mmol, 1.0 M) is added to a stirred solution of 1,3-dioxo-2-(1-tert-butoxycarbonyl-2,6-dioxopiperidin-3-yl)isoindoline(7.16 g, 20 mmol) in tetrahydrofuran (250 mL) at -40° C. After 1 hour, N-fluorobenzenesulfonimide (7.6 g, 24 mmol) is added to the mixture. The mixture is allowed to reach room temperature and kept overnight. The solution is stirred with ethyl acetate (200 mL), aqueous ammonium chloride (100 ml, sat), and water (100 mL). The aqueous layer is separated and extracted with ethyl acetate (200 mL). The combined organic layers are washed with water (100 mL), brine (100 mL), and dried over sodium sulfate. The solvent is removed in vacuo. The residue is purified by chromatography (silica gel) to give the intermediate 1,3-dioxo-2-(1-tert-butoxycarbonyl-2,6-dioxo-3-fluoropiperidin-3-yl)isoindoline.

후처리

  1. customto reach room temperature
  2. waitkept overnight
  3. customThe aqueous layer is separated
  4. extractionextracted with ethyl acetate (200 mL)
  5. washThe combined organic layers are washed with water (100 mL), brine (100 mL)
  6. dry with materialdried over sodium sulfate
  7. customThe solvent is removed in vacuo
  8. customThe residue is purified by chromatography (silica gel)

출처 및 근거

ORD 기록
ord-409a5f40fcc84c95b2080e2545cda4e3
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05955476

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