1,1'-Carbonyldiimidazole → (1R,2S)-ethyl 1-(1H-imidazole-1-carboxamido)-2-vinylcyclopropanecarboxylate

HRID 1675394노트

반응식

HRID 1675394 반응식
S(C1C=CC(C)=CC=1)(O)(=O)=O.[NH2:12][C@:13]1([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:15][C@H:14]1[CH:16]=[CH2:17].[CH:23]1[N:27]=[CH:26][N:25]([C:28](N2C=NC=C2)=[O:29])[CH:24]=1>C1COCC1>[N:25]1([C:28]([NH:12][C@:13]2([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:15][C@H:14]2[CH:16]=[CH2:17])=[O:29])[CH:24]=[CH:23][N:27]=[CH:26]1

참가 물질

4

반응물 2

HCID 682631,1'-CarbonyldiimidazoleHCID 46737761(1R,2S)-ethyl 1-amino-2-vinylcyclopropanecarboxylate 4-methylbenzenesulfonate

생성물 1

HCID 57816680(1R,2S)-ethyl 1-(1H-imidazole-1-carboxamido)-2-vinylcyclopropanecarboxylate수율 70%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Under nitrogen, (1R,2S)-ethyl 1-amino-2-vinylcyclopropanecarboxylate tosylate salt (5 g, 1 eq.) and CDI (2.7 g, 1.1 eq.) were dissolved in THF (50 mL) containing TEA (2.3 mL, 1.1 eq.). The reaction mixture was then refluxed overnight. The solvent was removed under reduced pressure. The residue was dissolved in DCM, and washed twice with water. The organic layer was dried over sodium sulfate and then concentrated. The residue was purified by chromatography on silica gel to yield compound 33 as pale yellow oil in 70% yield.

후처리

  1. temperatureThe reaction mixture was then refluxed overnight
  2. customThe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in DCM
  4. washwashed twice with water
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-829828b0f7654fb094befcc549e21ff9
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003659B2

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