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

HRID 220395

反応式

HRID 220395 の反応式
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]

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 66133Benzyl triethylammonium chloride触媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-50c7568dcc72409cbf31471272f78f13
出典データセット
uspto-grants-2012_06
特許番号
US08202881B2

関連ノート

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