Potassium Carbonate → Tert-butyl 1,3-dioxoisoindolin-2-yl(2-isopropoxyethyl)carbamate

HRID 220395

반응식

HRID 220395 반응식
CS(O[CH2:6][CH2:7][O:8][CH:9]([CH3:11])[CH3:10])(=O)=O.[O:12]=[C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[N:14]1[NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(OCC)(=O)C.O>[O:22]=[C:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13](=[O:12])[N:14]1[N:23]([CH2:6][CH2:7][O:8][CH:9]([CH3:10])[CH3:11])[C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29]

참가 물질

8

반응물 3

HCID 11430Potassium CarbonateHCID 801162N-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)(tert-butoxy)formamideHCID 184650452-Isopropoxyethyl Methanesulfonate

생성물 1

HCID 58180589Tert-butyl 1,3-dioxoisoindolin-2-yl(2-isopropoxyethyl)carbamate수율 83%

시약·촉매·용매 4

HCID 66133Benzyl triethylammonium chloride촉매HCID 962Water용매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

A round bottom flask charged with 2-isopropoxyethyl methanesulfonate (example 77A, 0.791 g, 4.34 mmol) in acetonitrile (21.70 mL) was stirred under an atmosphere of nitrogen. tert-Butyl 1,3-dioxoisoindolin-2-ylcarbamate (1.138 g, 4.34 mmol) was added along with potassium carbonate (2.399 g, 17.36 mmol) and benzyltriethylammonium chloride (0.198 g, 0.868 mmol). The reaction mixture was heated at 50° C. 24 h and cooled to rt over the weekend. The reaction mixture was diluted with ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. The combined organics were washed with brine, dried over anhydrous sodium sulfate, vacuum filtered through a plug of silica gel and concentrated in vacuo. The crude oil was used without additional purification (1.26 g, 83% yield).

후처리

  1. temperature24 h and cooled to rt over the weekend
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe combined organics were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate, vacuum
  5. filtrationfiltered through a plug of silica gel
  6. concentrationconcentrated in vacuo
  7. customThe crude oil was used without additional purification (1.26 g, 83% yield)

출처 및 근거

ORD 기록
ord-50c7568dcc72409cbf31471272f78f13
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202881B2

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