Methyl chloroformate → tert-butyl 4-(2,2-dimethylbutyl)-2-{2-[4-(5-fluoropyridin-2-yl)phenyl]-1-[(methoxy carbonyl)amino]ethyl}-1H-imidazole-1-carboxylate

HRID 1881468노트

반응식

HRID 1881468 반응식
C(N(CC)CC)C.Cl[C:9]([O:11][CH3:12])=[O:10].[NH2:13][CH:14]([C:29]1[N:30]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH:31]=[C:32]([CH2:34][C:35]([CH3:39])([CH3:38])[CH2:36][CH3:37])[N:33]=1)[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][N:23]=2)=[CH:18][CH:17]=1>>[CH3:39][C:35]([CH3:38])([CH2:36][CH3:37])[CH2:34][C:32]1[N:33]=[C:29]([CH:14]([NH:13][C:9]([O:11][CH3:12])=[O:10])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][N:23]=3)=[CH:18][CH:17]=2)[N:30]([C:40]([O:42][C:43]([CH3:45])([CH3:44])[CH3:46])=[O:41])[CH:31]=1

참가 물질

4

반응물 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 66705676tert-butyl 2-{1-amino-2-[4-(5-fluoropyridin-2-yl)phenyl]ethyl}-4-(2,2-dimethylbutyl)-1H-imidazole-1-carboxylate

생성물 1

HCID 66705856tert-butyl 4-(2,2-dimethylbutyl)-2-{2-[4-(5-fluoropyridin-2-yl)phenyl]-1-[(methoxy carbonyl)amino]ethyl}-1H-imidazole-1-carboxylate

실험 절차

Triethylamine (0.02 mL, 0.16 mmol) followed by methyl chloroformate (5 μL, 0.05 mmol) were added to an ambient temperature solution of tert-butyl 2-{1-amino-2-[4-(5-fluoropyridin-2-yl)phenyl]ethyl}-4-(2,2-dimethylbutyl)-1H-imidazole-1-carboxylate (24 mg, 0.05 mmol). After stirring at ambient temperature for 1 h, the reaction mixture was quenched with water and extracted with methylene chloride. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Preparatory plate chromatography eluting with 20% ethyl acetate/hexane afforded tert-butyl 4-(2,2-dimethylbutyl)-2-{2-[4-(5-fluoropyridin-2-yl)phenyl]-1-[(methoxy carbonyl)amino]ethyl}-1H-imidazole-1-carboxylate.

후처리

  1. customthe reaction mixture was quenched with water
  2. extractionextracted with methylene chloride
  3. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  4. concentrationconcentrated in vacuo
  5. washPreparatory plate chromatography eluting with 20% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-0f09ab7ae8c2474f8c6ed49520b50a86
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318767B2

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